TS. Cao c gic (Ch bin) ThS. H xun thu ThS.

Cao th vn giang

Thit k bi ging
Nng cao - Tp hai

Nh xut bn H ni
1

Chng VI Hirocacbon khng no

Bi 39 anken Danh Php, cu trc, ng phn

A. Mc tiu bi hc 1. Kin thc HS bit: Khi nim, cng thc chung ca dy ng ng anken, bit phn loi v gi tn mt s anken n gin. Cu trc electron v cu trc khng gian ca anken. Vit ng phn cu to v ng phn hnh hc ca anken. HS hiu: V sao anken c nhiu ng phn hn ankan tng ng. Nguyn nhn mt s anken c ng phn hnh hc l do s phn b cc nhm th cc v tr khc nhau i vi mt phng cha lin kt . 2. K nng T cng thc cu to bit gi tn v ngc li t tn gi vit c cng thc cu to nhng anken n gin. Vit ng phn hnh hc v ng phn cu to ca anken. B. chun b ca GV v HS GV: My tnh, my chiu, cc phiu hc tp. M hnh phn t etilen, ng phn cis-trans ca but-2-en. HS: n tp kin thc bi ankan v xem trc bi anken.

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I ng ng v danh php Hot ng 1 1. Dy ng ng v tn thng thng ca anken GV chiu m hnh phn t ca etilen HS quan st v tho lun. ln mn hnh cho HS quan st:

a)

b) Cng thc phn t ca mt s ng ng ca etilen: C3H6, C4H8, C5H10 T C2H4 theo khi nim ng ng. C2H4(CH2)k C2+kH4+k t 2+k = n th CnH2n (n 2). Etilen cu to c mt lin kt i (gm mt lin kt bn vng v mt lin kt km bn), vy: Anken l hirocacbon khng no mch h trong phn t c mt lin kt i.

yu cu HS tho lun v cc vn sau: Vit CTCT cc cht tip theo l ng ng ca C2H4. Lp cng thc chung dy ng ng ca etilen. Phn tch cu to ca etilen t nu nh ngha dy ng ng ca etilen.

GV yu cu HS nu cch gi tn thng HS gi tn. thng ca cc ankan sau? propan CH3CH2CH3 CH3CH2CH3, CH3 CH2CH2CH3, CH3CH2CH2CH3 butan CH3CHCH3, CH3CHCH3 isobutan CH3 CH3 GV b sung: Tn thng thng ca mt s anken n gin ly t tn ankan tng ng nhng i ui an thnh ui ilen.
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 Cn thm v tr ca lin kt i trc tn gi. V tr lin kt i trn nguyn t cacbon th 1, 2, tng ng gi l , GV yu cu HS gi tn thng thng cc anken c cng thc sau: CH2= CHCH3 CH2=CHCH2CH3 CH3 CH =CHCH3 CH2=C CH3 CH3 GV b sung tn gi ca mt s gc ca anken: CH2=CH gc vinyl CH2=CHCH2 gc anlyl Hot ng 2 2. Tn thay th GV chiu ln mn hnh tn gi ca mt HS quan st v tho lun. s anken n gin. CTCT CH2= CH2 CH2= CHCH3 CH3CH =CHCH3 CH2=C CH3 CH3 Tn gi eten propen

HS gi tn: CH2=CHCH3 CH2=CHCH2CH3 CH3 CH =CHCH3 CH2=C CH3 CH3 propilen -butilen -butilen isobutilen

CH2=CHCH2CH3 but-1-en but-2-en 2-metylpropen

Yu cu HS nhn xt rt ra quy lut gi Quy lut gi tn: S ch v tr nhnh Tn tn cc anken theo tn thay th. chnh GV hng dn HS chn mch chnh, - tn nhnh cch nh s mch C.

mch

- s ch v tr nguyn t C u tin cha lin kt i - en

 Mch chnh l mch cha lin kt GV yu cu HS gi tn cc anken sau i, di nht v cho nhiu nhnh nht. nh s C mch chnh bt u t theo tn thay th: pha gn lin kt i hn. CH2=CHCH2CH2CH3 HS gi tn: CH3 CH =CHCH2CH3 CH2=C CH2CH3 CH3 CH2=CH CHCH3 CH3 CH2=CHCH2CH2CH3 pent-1-en CH3CH =CHCH2CH3 pent-2-en CH2=C CH2CH3 2-metylbut-1-en CH3 CH2=CHCHCH3 3-metylbut-1-en CH3 II. cu trc v ng phn Hot ng 3 1. Cu trc GV chiu ln mn hnh cu trc ca HS quan st. etilen.

a)

b) HS tho lun v tr li: Nguyn t cacbon ni i trng thi lai ha sp2 (lai ho tam gic). Lin kt i gm 1 lin kt (bn vng) v 1 lin kt (km bn). Hai nguyn t C v bn nguyn t H u nm trn cng mt mt phng. Gc lin kt HCH v HCC gn bng nhau v bng 1200 .
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GV yu cu HS tho lun cc vn sau: Trng thi lai ho ca nguyn t C. Cu to ca lin kt i.

V tr tng i ca cc nguyn t. Gc lin kt HCC, HCH.

 Kh nng quay ca cc nguyn t Hai nguyn t C khng th quay t quanh trc lin kt i. do quanh trc lin kt C=C (do cn tr bi lin kt ). Hot ng 4 2. ng phn a) ng phn cu to GV yu cu HS: Nu khi nim ng phn. Da theo cng thc cu to th anken c chia thnh nhng loi ng phn no? HS tho lun v tr li: ng phn l nhng hp cht khc nhau nhng c cng cng thc phn t. Da theo cng thc cu to c phn lm 2 nhm: ng phn mch C. ng phn v tr lin kt i.

Vit cc ng phn cu to v gi tn HS vit ng phn ca C5H10v gi tn: anken c cng thc phn t C5H10. CH2=CHCH2CH2CH3 pent-1-en CH3CH =CHCH2CH3 pent-2-en CH2=CHCHCH3 3-metylbut-1-en CH3 CH3 CH2C=CH2 2-metylbut-1-en CH3 CH3 CH =CCH3 2-metylbut-2-en CH3 b) ng phn hnh hc GV chiu m hnh phn t ng phn cis trans ca but2-en ln mn hnh. HS quan st v tho lun.

GV nu vn : nh vy but-2-en c ng phn cis v ng phn trans vy iu kin no c ng phn cis-trans? GV hng dn, iu khin HS gii quyt vn . Cu trc ca lin kt i C=C. Cu trc khng gian ca lin kt i C=C, s phn b ca cc lin kt n quanh C c ni i. Yu cu HS rt ra iu kin c ng phn cistrans v khi nim v ng phn hnh hc (cis trans).

HS tham gia gii quyt vn : Lin kt i gm 1 lin kt v 1 lin kt . Cc nguyn t xung quanh lin kt i C=C nm trn mt mt phng nn khng th quay c quanh trc lin kt. C th nu s sau gii thch. R1 R3 C=C R4 R2 R3 R 4 iu kin: R1 R2 + ng phn cis: khi mch chnh nm cng mt pha ca lin kt C= C. + ng phn trans: Khi mch chnh nm pha khc nhau ca lin kt C= C.

Vit ng phn hnh hc ca pent-2-en.

HS vit ng phn hnh hc pent-2-en. C 2H 5 H 3 C H 3C H C=C C=C H C2 H 5 H H cis-pent-2-en trans-pent-2-en

Hot ng 5 Cng c bi v bi tp v nh 1. Cng c bi: GV khc su mt s kin thc cho HS v:

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 Cng thc chung ca anken. Cu to ca lin kt i. Quy tc gi tn anken. Cc loi ng phn ca anken. GV chiu mt s bi tp sau ln mn hnh cho HS tho lun: 1. Gi tn anken sau: CH3 CH3 C CH2C = CHCH3 CH3 C2H 5 B. 2,2-imetyl-5-etylhex-4-en D. 4-imetyl-2,2-imetylhex-4-en p n A. 2. Cho 3 hirocacbon sau: CH3 CH2C=CH2 CH3 CH3 CH2C=CHCH3 CH3 CH3 CH2C=CHCH3 C 2H 5 A. 1, 2, 3 B. 2 (3) (1) A. 3-etyl-5,5-imetylhex-2-en C. 3-etyl-5,5-imetylhex-3-en

(2)

Hirocacbon no cho ng phn cis-trans? C. 1, 3 D. 2, 3 p n B. 3. Trong phn t cc anken, theo chiu tng s nguyn t cacbon, phn trm khi lng ca cacbon: A. C. Tng dn Khng i B. Gim dn D. Bin i khng theo quy lut. p n C. 2. Bi tp v nh 1, 2, 3, 4, 5 (SGK).

D. Hng dn gii bi tp SGK 1. a) S; b) S ; c) ; d) . 2. Cng thc phn t CnH2n (n 2) Cng thc cu to chung: R1R2C=CR3R4. Dng bng sau so snh: Ankan Thnh phn Cu to Cha C v H. Mch h. Trong phn t ch c lin kt n. 3. a) CH3 CH2CH=CHCH3 b) CH3 CH2C=CH2 CH3 c) CH3 CH2CH=CCH3 CH3 d) CH2=CCH3 CH3 e) CH3 CH2CH2C=CHCH3 CH3 g) CH3C = CCH3 CH3 CH3 4. a) Xiclobutan l ng phn ca buten, thuc loi ng phn cu to (khc nhau v bn cht nhm chc). b) Th d cng s nguyn t C l 4, C4H10 c hai ng phn nhng C4H8 c ba ng phn cu to, trong c mt ng phn cu to c ng phn hnh hc: C4H10 : CH3CH2CH2CH3 CH3 CHCH3 CH3
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Anken Cha C v H. Mch h. Trong phn t c mt lin kt i C=C.

Xicloankan Cha C v H. Mch vng. Trong phn t ch c lin kt n.

C4H8: CH3CH=CHCH3 H3C C=C H H CH3

CH3 CH2CH=CH2 H 3C C=C H CH3 H

CH3 C=CH2 CH3

5. a) But-2-en c ng phn hnh hc cis v trans cn but-1-en th khng c, do cu to ca but-2-en tho mn hai iu kin: C cha lin kt i C=C. Mi nguyn t C mang lin kt i nh vi hai nhm nguyn t khc nhau. b) 6 penten ng phn l: A: B: CH3 CH2CH=CHCH3 pent-2-en CH3 CH2C=CH2 CH3 2-metylbut-1-en C: H3C C=C H cis-pent-2-en H C2H 5 H 3C H C=C C2H 5 H trans-pent-2-en CH3 CH2CH2CH=CH3 pent-1-en CH3 CHCH=CH2 CH3 3-metylbut-1-en CH3C=CHCH3 CH3 2-metylbut-2-en

Cc cht dy A (mch khng nhnh) v dy B (mch c nhnh) l ng phn mch C ca nhau. Hai cht trong dy A cng nh trong dy B l ng phn v tr nhm chc. Hai cht trong dy C l ng phn hnh hc.

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Bi 40

anken tnh cht, iu ch v ng dng

A. Mc tiu bi hc 1. Kin thc HS bit: Quy lut bin i nhit nng chy, nhit si ca anken. Tnh cht ho hc c trng ca anken l phn ng cng, iu ch v mt s ng dng ca anken. Cch phn bit ankan vi anken bng phng php ho hc. HS hiu: Nguyn nhn gy ra phn ng cng, phn ng trng hp, phn ng oxi ho khng hon ton l do cu to ca phn t anken c lin kt . C ch cng axit vo anken, ni dung quy tc Mac-cp-nhi-cp. 2. K nng Gii bi tp lin quan n anken. Vit phng trnh ho hc minh ho tnh cht ho hc ca anken. 3. Tnh cm, thi Anken v sn phm trng hp c nhiu ng dng trong i sng sn xut. V vy, gip HS thy c tm quan trng ca vic nghin cu anken. B. chun b ca GV v HS GV: My tnh, my chiu, cc phiu hc tp. Ho cht: Nc brom, H2SO4 c, etanol, thuc tm. Dng c: ng nghim, nt cao su c gn ng dn kh, kp ng nghim, n cn, b gi th nghim. HS: n tp kin thc bi ankan v xem trc bi anken.

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C. tin trnh dy hc Hot ng ca GV Hot ng 1 Kim tra bi c GV chiu hai bi tp ln mn hnh yu cu HS tho lun. 1. Nu iu kin c ng phn cis- HS 1: Dng s sau: trans. Cho v d minh ho? R1 C=C R2 iu kin: R1 R2 R4 R 3 R4 R3 Hot ng ca HS

+ ng phn cis: Khi mch chnh nm cng mt pha ca lin kt C= C. + ng phn trans: Khi mch chnh nm pha khc nhau ca lin kt C= C. V d: H 3C C=C H H cis-but-2-en 2. Anken c cng thc CH3C =CHCH2CH3 CH3 Tn thay th ca anken l: A. 3-metylpent-3-en B. 2-metylpent2-en C. 2-metylpent-3-en D. 3-etylbut-2-en GV nhn xt kt qu bi lm ca 2 HS cho HS khc rt kinh nghim.
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CH3

H3C C=C

CH3 H trans-but-2-en

HS 2 chn p n ng.

p n B.

I. tnh cht vt l Hot ng 2 1. Nhit si, nhit nng chy v khi lng ring GV chiu li bng 6.1 ln mn hnh cho HS quan st, yu cu HS nhn xt quy lut bin i cc tnh cht sau ca anken: Trng thi. Nhit si. Nhit nng chy. Khi lng ring. HS tho lun ln lt tr li cc cu hi ca GV, rt ra nhn xt: Trng thi: + 3 anken u l cht kh. + Cc anken khc l cht lng hoc rn. t0nc, t0s v khi lng ring tng theo chiu tng ca phn t khi. Anken nh hn nc. 2. Tnh tan v mu sc GV yu cu HS nghin cu SGK v HS nghin cu SGK v tr li: nhn xt v tnh tan v mu sc ca Anken ho tan tt trong du m, hu anken. nh khng tan trong nc. Anken l nhng cht khng mu. II. tnh cht ho hc Hot ng 3 GV yu cu HS rt ra nhng nhn xt HS c im cu to ca anken: c mt chung v mi quan h gia c im lin kt i (mt lin kt bn vng v mt lin kt km bn). cu to v tnh cht ca anken. Lin kt i d on l trung tm phn ng. Phn ng ph v lin kt km bn. 1. Cng hiro GV yu cu HS: Nhc li khi nim phn ng cng. HS tho lun. Phn ng cng l phn ng trong

phn t hp cht hu c kt hp vi phn t khc to thnh phn t

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hp cht mi. Nu iu kin xy ra phn ng Khi c xc tc Ni v un nng. cng H2 vo anken, vit phng trnh Phng trnh ho hc: ho hc gia etilen v H2. Ni CH2 = CH2 + H2 CH3CH3 t
o

Vit phng trnh ho hc tng Phng trnh ho hc tng qut: Ni qut anken cng H2. CnH2n+2 CnH2n + H2 to Sn phm phn ng cng hiro vo (Sn phm thu c l ankan) anken l g?
2. Cng halogen GV lm th nghim : HS quan st v tho lun. Dn t t kh etilen (t ti ng kh) Thy dung dch brom (mu nu ) b vo dung dch brom, yu cu HS quan nht dn, chng t nng Br2 gim. st gii thch hin tng bng phng trnh ho hc. Gii thch: Do brom tn cng vo lin GV hng dn HS gii thch hin kt i ph v lin kt . tng. Phng trnh ho hc. CH2=CH2 + Br2(dd) CH2BrCH2Br 1,2-ibrometan GV yu cu HS nu ng dng ca ng dng: phn bit anken vi ankan phn ng anken vi brom. do ankan khng lm mt mu dung dch brom iu kin thng. GV hng dn HS nghin cu th HS nghin cu SGK. nghim hnh 6.3 trong SGK, yu cu HS: Kt lun etilen cng clo to thnh cht Rt ra kt lun. lng dng du, khng tan trong nc, p sut trong ng nghim gim lm cho nc dng ln.

Vit phng trnh ho hc gia Vit phng trnh ho hc. CH2=CH2 + Cl2 CH2ClCH2Cl etilen vi Cl2.
1,2-icloetan

Vit phng trnh tng qut gia Phng trnh tng qut:
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anken vi halogen, sn phm to CnH2n + X2 CnH2nX2 thnh l g? Sn phm to thnh l dn xut ihalogen. 3. Cng HX (X l OH, Cl, Br) a) Cng axit GV gi HS vit phng trnh ho HS vit phng trnh ho hc: hc ca anken vi hirohalogenua CH2=CH2 + HBr CH3CH2Br (HCl, HBr, HI), axit H2SO4 m c. etyl bromua CH2=CH2 + HCl CH3CH2Cl etyl clorua CH2=CH2 + H2SO4 CH3CH2OSO3H etyl hirosunfat GV chiu s chung axit cng vo HS quan st, phn tch v tr li. anken ln mn hnh cho HS quan st: C=C + H A C=C H A C=C H + (1)

C=C

+ HA

C=C + + A C=C H H A Yu cu HS nhn xt v:

(2)

Phn ng xy ra qua bao nhiu giai Phn ng xy ra qua 2 giai on. on. Kiu phn ct phn t HA. bn ca cacbotion trung gian. Phn t HA b phn ct kiu d li. Cacbocation l tiu phn trung gian khng bn.

Phn t no tn cng vo ni i Phn mang in tch dng tn cng trc. trc.

b) Cng nc (phn ng hirat ho) GV gi HS vit phng trnh ho HS: iu kin thch hp (c H+ xc tc v
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hc ca phn ng etilen cng nc.

un nng), anken c th cng nc.

H ,t CH2=CH2+H2O CH3CH2OH
+ o

etanol c) Hng ca phn ng cng axit v nc vo anken GV vit s phn ng cng ca HS quan st, tho lun v tr li. propen vi HCl. CH3CH2CH2Cl 1- clopropan CH CH=CH +
3 2

CH3CHCH3 Cl 2- clopropan GV yu cu HS nhn xt sn phm Phn ng gia propilen vi HBr cho 2 chnh v sn phm ph t rt ra sn phm: quy tc Mac-cp-nhi-cp. 1- clopropan l sn phm ph. GV hng dn HS rt ra quy tc 2- clopropan l sn phm chnh. Mac-cp- nhi-cp. Quy tc Mac-cp-nhi-cp: Trong phn ng vi cng HA hoc nc vo lin kt i, nguyn t H (hay phn mang in tch dng) u tin cng vo nguyn t C bc thp hn (cacbon c nhiu hiro hn), cn A (phn mang in tch m) u tin cng vo nguyn t C bc cao hn (cacbon c t hiro hn). GV yu cu HS vit phng trnh ho HS vit phng trnh ho hc. hc ca isobutilen vi H2O. CH3CHCH2OH CH3 sn phm ph CH3C=CH2+ H2O OH CH
3

CH3CCH3 CH3
sn phm chnh

GV chiu ln mn hnh mt bi tp HS tho lun v chn. trc nghim nh sau: Trng hp no ng cho quy tc
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Mac-cp-nhi-cp. A. Anken bt i xng cng vi X2. B. Anken i xng cng vi HX. C. Anken bt i xng cng vi HX. D. Anken i xng cng vi X2. p n C. Hot ng 4 4. Phn ng trng hp GV yu cu HS nghin cu SGK ri HS nghin cu SGK v tho lun tr li cc cu hi sau:
Vit phng trnh phn ng trng Phng trnh ho hc. o xt,t hp etilen. n CH2 = CH2 (CH2CH2)n Nu ngha ca cc i lng. etilen polietilen

T rt ra khi nim phn ng CH = CH : gi l monome. 2 2 trng hp, cch gi tn. n: l h s trng hp (thng ly gi tr trung bnh).

Phn ng trng hp l qu trnh cng hp lin tip nhiu phn t nh ging nhau hoc tng t nhau to thnh nhng phn t rt ln (gi l polime). Tn polime = poli + tn monome. Tng t yu cu HS vit phng trnh Phng trnh ho hc: o xt,t trng hp ca propilen v but-2-en. nCH3 CH =CH2 (CHCH2) n
CH3 propilen
o

polipropilen

xt ,t nCH3CH=CHCH3 (CH CH)n

CH3 CH3 polibutilen

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Hot ng 5 5. Phn ng oxi ho a) Phn ng oxi ho hon ton GV lm th nghim t chy etilen HS quan st th nghim v nhn xt. trong khng kh yu cu HS nhn xt:

Mu ngn la. Sn phm to thnh.

Ngn la khng mu, sng xanh. Sn phm kh, khng mi.

Vit phng trnh phn ng chy Phng trnh chy. o t ca etilen. 2C2H4 + 5O2 4CO2 + 4H2O o Vit phng trnh ho hc chy t 2nCO2 + 2nH2O CnH2n + 3nO2 tng qut ca anken. T l n CO2 : n H2 O = 1 : 1 T l n H2O v n CO2 .
b) Phn ng oxi ho khng hon ton GV lm th nghim: Sc kh etilen HS quan st th nghim. vo dung dch KMnO4 (l) yu cu HS: Hin tng: Dung dch KMnO4 mu tm Nu hin tng. b nht dn, c kt ta nu en xut hin. Gii thch.

ng dng ca phn ng.

Gii thch:

GV tng t yu cu HS vit phng Etilen phn ng vi dung dch KMnO4 trnh ho hc ca anken vi dung lm cho nng KMnO4 gim nn mu tm nht dn, sinh ra MnO2 kt ta mu dch KMnO4. nu en. 3CH2=CH2 + 4H2O + 2KMnO4 3CH2 CH2 + 2MnO2 + 2KOH OH OH

ng dng phn bit anken vi ankan.

HS vit phng trnh ho hc tng qut. GV: Gi HS vit phng trnh ho 3CnH2n + 4H2O + 2KMnO4 hc tng qut. 3CnH2n(OH)2 + 2MnO2 + 2KOH

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III. iu ch v ng dng Hot ng 6 1. iu ch + Trong phng th nghim: GV gii thiu: Etilen c iu ch t etanol theo phng trnh ho hc:
H 2 SO 4 c C2H5OH o C2H4 + H2O 170 C

HS tho lun.

Phng php iu ch ny thng ln cc kh nh CO2, SO2. Vy dng cch no loi b SO2, CO2, t yu cu HS trnh by cch lp rp b dng c iu ch C2H4 sch.

SO2, CO2 l oxit axit nn dng mt baz mnh nh dung dch NaOH. Hn hp kh trc khi thu dn qua bnh ng dung dch NaOH.
HS tho lun cch lp dng c c lp nh hnh sau:

HS trong cng nghip anken c iu GV yu cu HS nu phng php ch t ankan bng phng php. iu ch anken trong cng nghip v hiro ho ankan: xt vit phng trnh ho hc minh ho. CnH2n + H2 Cn H2n + 2 o + Trong cng nghip:
t ,p

Crackinh ankan
xt Cn H2n + 2 Cp H2p +2 + CmH2m t o ,p

2. ng dng GV: Su tp mu vt, tranh nh, mt HS tho lun nhng ng dng chnh ca s ng dng c bn ca anken. Chiu anken:
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ln mn hnh cho HS quan st (hoc Nguyn liu cho tng hp ho hc. cho HS nghin cu SGK). V d: axit hu c, keo dn Yu cu HS khi qut ho ng dng Phng trnh ho hc: O o ca anken, vit phng trnh ho hc Ag,t 2CH2=CH2 + O2 2CH2 CH2 minh ho (nu c). Tng hp polime. v d
xt,t n CH2 = CH2 (CH2 - CH2)n p
o

Lm dung mi
Hot ng 7 Cng c bi bi tp v nh 1. Cng c bi GV nhc li cc ni dung cn nm vng cho HS:

Tnh cht vt l ca anken. Phn ng cng H2, X2, HA v quy tc cng Mac-cp-nhi-cp. Phn ng trng hp v oxi ho.
GV chiu ln mn hnh cc bi tp sau luyn tp. 1. Khi cng HBr vo hn hp cc HS tho lun. ng phn mch h C4H8 th thu c ti a bao nhiu sn phm. A. 3 B. 4 C. 5 D. 6 p n C.

2. nhn bit CH4 v C2H4 ta dng HS tho lun. dung dch no sau y: A. NaOH B. KMnO4 C. HCl D. CuSO4 p n B.

2. Bi tp v nh 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 (SGK)

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D. Hng dn gii bi tp SGK 1. a) ; b) ; c) S ; d) .

2. Anken hot ng ho hc hn hn ankan l do trong phn t c cha lin kt , y l nhng lin kt km bn nn c kh nng phn ng d dng hn. Cc phng trnh ho hc:
CCl 4 a) CH3 CH =CH2 + Br2 CH3 CHBrCH2Br

b) CH3CH=CH2 + HI CH3CHICH3 c) CH3CH=CH2 + H2SO4 (c) CH3CHCH3 OSO3H d) CH3CH=CH2 + H2O CH3CHOHCH3 e) 3CH3CH=CH2 + 2KMnO4 + 4H2O 3CH3CHOHCH2OH + 2KOH +2MnO2
t ,p C H CH 2 g) n CH3CH =CH2 | CH 3 n 3. b) Trng hp isobutilen
o

H + ,t o

CH 3 | t o ,p CH C n CH2= C CH 3 | | CH3 CH 3 n

Vi n = 15.000 th PTK trung bnh ca polime l : 15.000 x 56 = 840000 4. t cng thc phn t olefin l CnH2n. Phng trnh ho hc ca phn ng
Ni ,t vi hiro:CnH2n + H2 CnH2n + 2 0, 448 0,02 = 0, 02 22, 4
o o

Phng trnh ho hc ca phn ng vi brom: CnH2n + Br2 CnH2nBr2 0,02 0,02 Vy ta c: (14n + 160) x 0,02 = 4,32 n = 4. Cng thc phn t l C4H8. V ankan thu c l mch nhnh, do CTCT ca olefin l: CH2=CCH3 CH3 (2-metylpropen)
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5.

A1 : CH2=CCH2CH3 CH3 A2 : CH3 C=CHCH3 CH3 A3 : CH3CHCH=CH2 CH3

: 2-metylbut-1-en : 2-metylbut-2-en : 3-metylbut-1-en

A1, A2 v A3 cng mch C nh nhau (khi hiro ho ra cng mt ankan), ch khc v tr nhm chc (C=C). Chng l ng phn v tr nhm chc.
6. CnH2n+2 : a (mol) ; CnH2n : a(mol).

- S mol Br2 = 0,1 (mol), S mol CO2 = 0,6 (mol) CnH2n + Br2 CnH2nBr2 0,1 0,1 3n + 1 to CnH2n+2 + nCO2 + (n+1)H2O O2 2 0,1 0,1n 3n to CnH2n + O2 nCO2 + nH2O 2 0,1 0,1n a) 0,1n + 0,1n = 0,6 n = 3 CTCT ca ankan l C3H8 (m = 44g/mol), CTCT : CH3CH2CH3; CTCT ca ankan l C3H6 (m = 42g/mol), CTCT : CH2=CHCH3. b) Mhh =

0, 1, 4 4 + 0, 1 .4 2 43 = 4, 3g / m o l d h h / k k = = 1, 4 8 0, 1 + 0, 1 29
8 = 0,05 (mol) 160

7. S mol Br2 =

CnH2n + Br2 CnH2nBr2 0,05 2,8 MA = = 56 (g/mol) 0,05 Vy CTPT ca A l : C4H8. Cc cng thc cu to: CH2=CHCH2CH3; CH2=CCH3; CH3
22

0,05

14n = 56

n = 4.

CH3CH=CHCH3

Khi hirat ho A ch thu c mt ancol duy nht. Vy CTCT ca A l: CH3CH=CHCH3 Cu trc: H3C

CH3 C=C H

H3C C=C H

H CH3

8. a) ng nghim th nht chuyn thnh ng nghim b) hnh 6.5. Hexan Khng phn ng vi dung dch KMnO4, khng tan trong dung dch KMnO4 nn cht lng phn lm 2 lp, dung dch khng nht mu. ng nghim th hai chuyn thnh ng nghim c) hnh 6.5. Hex-1-en c phn ng oxi ho vi dung dch KMnO4 lm nht mu dung dch KMnO4, sn phm sinh ra khng tan trong nc v vy phn lm hai lp.

b) Phng trnh ho hc: 3CH2CH2CH2CH2CH=CH2 + 2KMnO4 + 4H2O 3CH3CH2CH2CH2CHCH2 + 2MnO2 + 2KOH OH OH 9. Phng trnh ho hc: CH2=CHCH2CH3 CH3CH2CH2CH3
5000C

(I) (II)

- H2

CH3CH=CHCH3

Cng thc cu trc ca (II) CH3 H3C

H 3C

C=C CH3 H H cis-but-2-en trans-but-2-en 10. V etilen v propilen c th tng hp ra polime v cc ho cht hu c khc. Th d: H
t ,p nCH2 = CH2 (CH2 CH2 )n xt
o

C=C

CH2=CH2 + Cl2 CH2Cl CH2Cl

500 C CH2 =CHCl + HCl CH2 =CH2 + Cl2
o

t ,p CH 2 C H nCH2 = CHCl xt | Cl n o 1 as,t CH2 = CH2 + O2 CH 2 CH 2 2 O

o

(etilen oxi)

23

t ,p nCH2 = CH CH3 CH 2 C H xt | CH 3 n
o

500 C CH2=CH CH3 + Cl2 CH2=CH CH2Cl + HCl

o

H 2 SO 4 CH2=CH2 + H2O CH3CH2OH

E. T liu tham kho

S c mt ca lin kt trong phn t anken lm cho anken c kh nng phn ng cao hn nhiu so vi ankan, trong phn ng cng electrophin (k hiu AE) vo ni i l phn ng c trng nht. Theo quan nim hin nay, hu ht mi phn ng AE ca anken l nhng phn ng nhiu giai on hay cng tng bc. giai on u (chm) tc nhn electrophin (mang in dng) tn cng vo nguyn t cacbon mang in m () ca ni i b phn cc ho to ra cacbocation trung gian. Tip theo, giai on sau (nhanh) cacboncation s tc dng vi phn mang in m ca phn t tc nhn hoc dung mi to ra sn phm cng.
Chm Br V d: CH2=CH2 + HBr CH3 C H 2 CH3CH2Br nhanh -Br:

Chm CH2 = CH2 + Br2 CH2 -Br:

Br | Br CH2 C H2 C H2 nhanh | Br Br

Trong cc phn ng cng trn, nu giai on sau c mt cc cht nucleophin nh H2O, I, Cl, th s sinh ra sn phm cng cc cht nucleophin vo cacbocation:
H2 O H 2 SO 4 long H CH2=CH2 + H CH3 C H 2 CH3CH2 O H 2 CH3CH2OH to

Br
NaCl CH2 = CH2 + Br2 CH2

BrCH2CH2Br

(54%)

CH2

Br Cl

BrCH2CH2Cl (46%)

24

Phn ng cng ca mt tc nhn bt i xng (nh HCl, H2SO4, HOH, HBr, ICl,) vo mt anken bt i xng (nh CH3CH=CH2, CH3CH=CHCH2CH3,) s u tin xy ra theo hng to thnh cacbocation trung gian bn hn (quy tc Mac-cp-nhi-cp). V d: CH3CH=CH2 + HBr -Br

+ Br CH3CHCH3
(bn hn)

CH3CHBrCH3 (95%)

+ CH3CH2CH2 Br CH3CH2CH2Br (5%)

(km bn)

25

Bi 41
A. Mc tiu bi hc 1. Kin thc
HS bit:

ankaien

Khi nim v ankaien v c im cu trc ca h lin kt i lin hp Tnh cht, phng php iu ch v ng dng ca buta-1,3-ien v isopren.
HS hiu:

Nguyn nhn gy ra phn ng cng v phn ng trng hp kiu 1,4 do cu to ca phn t ankaien c lin kt lin hp. HS vn dng: Vit c mt s phng trnh ho hc lin quan n ankaien.
2. K nng

Quan st th nghim, m hnh phn t. Rt ra nhn xt v cu to v tnh cht ca ankaien. D on c tnh cht ho hc, kim tra v kt lun. Vit phng trnh ho hc minh ho tnh cht ho hc ca buta-1,3-ien.
3. Tnh cm, thi
Ankaien v sn phm trng hp c nhiu ng dng trong i sng sn xut, lm HS thy c tm quan trng ca vic nghin cu ankaien t to cho HS nim hng th trong hc tp.

B. chun b ca GV v HS

GV: My tnh, my chiu, cc phiu hc tp. M hnh phn t butaien. Ho cht, m cao su, mt s vt liu bng cao su (vng giun). HS: n tp bi anken v xem trc bi ankaien.

26

C. tin trnh dy hc Hot ng ca GV Hot ng 1 Kim tra bi c

GV gi 2 HS ln bng trnh by cc vn sau, cc HS khc chun b nhn xt v b sung. 1. T cu to ca anken nu tnh cht HS 1: Etilen c cu to gm 1 lin ho hc ca etilen v nu v d minh kt i (c lin kt km bn). ho? Phn ng cng hiro (phn ng hiro ho):
Ni CH3 CH3 CH2 = CH2 + H2 to

Hot ng ca HS

Phn ng cng brom:

CH2=CH2 + Br2(dd) CH2BrCH2Br 1,2-ibrometan Phn ng trng hp:
xt,t nCH2 = CH2 (CH2CH2)n etilen polietilen Phn ng oxi ho: 3CH2=CH2 + 4H2O + 2KMnO4 3CH2CH2 + 2MnO2 + 2KOH OH OH 2. Trnh by phng php ho hc HS 2: Sc t t hn hp qua dung tch ly kh metan tinh khit t hn hp dch brom th etilen b hp th: metan v etilen. CH =CH + Br CH BrCH Br
o

2(dd)

Kh khng b hp th l metan sch.

I. phn loi Hot ng 2

GV chiu cng thc cu to thu gn mt HS quan st v tho lun. s ankaien ln mn hnh.
27

CH2= C = CH2 CH2= C = CH CH3 CH2= C CH2= CH2 CH3

propaien buta-1,2-ien

CH2= CH CH =CH2 buta-1,3-ien

3-metylbuta-1,3-ien (isopren) Yu cu HS nhn xt:

C 2 lin kt i C=C trong phn t.

c im chung v rt ra khi nim u l hirocacbon khng no mch ankaien. h. Lp cng thc tng qut ca ankaien? Khi nim ankaien:
Ankaien l hirocacbon khng no mch h trong phn t c hai lin kt i.

T propaien.
C3H4 C3H4(CH2)k C3 + k H4 + 2k t k = n 3 CnH2n 2 (n 3) GV yu cu HS nghin cu SGK v tr HS nghin cu SGK v tho lun: li cc cu hi sau: Da vo v tr tng i gia hai C s phn loi ankaien. lin kt i.

C th chia ankaien thnh nhng loi C th chia ankaien thnh 3 loi: no? Cho v d minh ho. + Ankaien c 2 lin kt i cnh nhau. Trong cc loi ankaien nu th loi V d: CH2=CH=CH2 no quan trng nht? V sao? + Ankaien c hai lin kt i cch nhau 1 lin kt n (ankaien lin hp).
V d: CH2= CH CH =CH2 + Ankaien c 2 lin kt i cch xa nhau. V d: CH2= CH CH2 CH =CH2 Trong cc ankaien trn th ankaien lin hp quan trng nht v c nhiu ng dng trong thc t.

28

GV chiu ln mn hnh cng thc cu HS quan st tho lun. to thu gn v tn gi ca mt s ankaien. CH2= C = CH2 CH2= C = CH CH3 CH2= CHCH =CH2 CH3 propaien buta-1,2-ien buta-1,3-ien (isopren)

CH2=CCH2=CH2 2-metylbuta-1,3-ien CH2=CHCH2CH=CH2 penta-1,4-ien Yu cu HS rt ra cch gi tn ankaien. HS a ra quy tc gi tn: Tn mch chnh

s ch v tr lin kt i ien

II. cu trc phn t v phn ng ca butaien v Isopren Hot ng 3 1. Cu trc phn t butaien
GV chiu m hnh phn t ca buta-1,3- HS quan st tho lun. ien ln mn hnh:

yu cu HS tho lun:

Trng thi lai ho ca nguyn t C. V tr tng i ca cc nguyn t. c im ca 2 lin kt .

Cc nguyn t C u trng thi lai ho sp2. 4 nguyn t C v 6 nguyn t H u nm trn mt mt phng. Ankaien c hai lin kt i lin hp to nn s xen ph electron trn ton b trc cacbon.

C hai u c lin kt i (lin kt So snh cu to ca buta-1,3-ien vi km bn) butaien c lin kt etilen, t rt ra tnh cht ho hc ca lin hp nn bn hn lin kt trong buta-1,3-ien. etilen.
29

GV hng dn HS phn tch cu to v Tnh cht ho hc ca butaien ging anken: C phn ng cng, phn so snh vi etilen. ng trng hp, phn ng oxi ho khng hon ton.

Hot ng 4 2. Phn ng cng ca butaien v isopren

GV chiu li m hnh buta-1,3-ien ln HS quan st tho lun. mn hnh v yu cu HS phn tch khi Vi t l (1:1) X2 c th tn cng cng X2 vo buta-1,3-ien th X c kh vo: nng cng vo cc v tr no, gii thch V tr 1,2 ph v 1 lin kt . cc t l mol phn ng khc nhau? V tr 1,4 ph v c hai lin kt v to thnh mt lin kt i gia.

V tr 1,3 khng th c v khng m bo ho tr cho cc nguyn t.

Vi t l (1:2) th ph v c hai lin kt i, cng vo tt c cc v tr.

a) Cng hiro
GV tng t vi anken yu cu HS vit HS vit phng trnh ho hc tng phng trnh ho hc ca ankaien vi qut Ni H2 v cho v d, sn phm thu c l CnH2n 2 + 2H2 CnH2n + 2 to g? V d:
Ni CH2=CHCH=CH2 + 2H2 to

CH3CH2CH2CH3 Sn phm thu c l ankan.

b) Cng halogen v hirohalogen

GV cho HS bit:

T l % sn phm cng 1,2:

800C khong 80%, 400C khong 20%

T l % sn phm cng 1,4:

800C khong 20%, 400C khong 80%

HS tu vo nhit phn ng.

nhit rt thp u tin cng

30

GV: iu kin no th u tin cng vo v tr 1,2. vo v tr 1,2 hay cng vo v tr 1,4. nhit cao hn u tin cng vo v tr 1,4. GV trn c s phn tch, yu cu HS HS vit phng trnh ho hc. vit phn ng ca buta-1,3-ien vi Cng1,2. brom theo cc t l mol khc nhau. 80o C CH2 =CH CH=CH2+Br2 CH2=CHCHCH2 Br Br

Cng 1,4.
40 C CH2=CH CH=CH2 + Br2
o

CH2CH=CHCH2 Br Cng ng thi vo c hai lin kt i. CH2=CH CH=CH2 + 2Br2 (d ) CH2CH CH CH2 Br Br Br Br GV cho bit tng t vi anken: HS tho lun phn ng cng HX. ankaien phn ng vi HX tun theo quy tc Cng 1,2 Mac-cp-nhi-cp v yu cu HS vit 80o C CH2=CH CH=CH2 +HBr phng trnh phn ng minh ho (to ra CH2=CH CHCH3 sn phm chnh). Br

Cng 1,4

Br
o

40 C CH2=CHCH=CH2 + HBr

GV b sung: Isopren c phn ng tng t buta-1,3-ien. GV chiu bi tp sau ln mn hnh cho HS tho lun: Cho buta-1,3-ien cng HBr (1:1) cho ti a bao nhiu sn phm? L nhng sn phm no?

CH3CH=CHCH2Br HS tho lun v tr li c bn sn phm l: CH2= CH CH2 CH2Br CH2= CH CH CH3 Br

31

H3C C=C H H C=C

CH2Br H CH2Br

H H 3C GV: T cc phn ng trn yu cu HS rt HS tho lun rt ra nhn xt: ra nhn xt tnh cht ca buta-1,3-ien. Butaien v isopren c kh nng tham gia phn ng cng. GV hng dn HS rt ra nhn xt.

nhit thp u tin to thnh sn phm cng 1,2, nhit cao u tin to thnh sn phm cng 1,4. Phn ng cng HX theo quy tc Mac-cp-nhi-cp.
c) Phn ng trng hp
GV yu cu HS nhc li khi nim phn HS: Phn ng trng hp l qu ng trng hp, iu kin c phn ng trnh cng hp lin tip nhiu phn t nh ging nhau hoc tng t nhau trng hp. to thnh nhng phn t rt ln (gi l polime). GV b sung: Khi c mt cht xc tc, nhit , p iu kin c phn ng trng sut thch hp, buta-1,3-ien v isopren hp l c mt cht xc tc, nhit tham gia phn ng trng hp ch yu theo , p sut thch hp. kiu cng 1,4 to thnh cc polime m mi mt xch c cha mt lin kt i gia.

Yu cu yu cu HS vit sn phm HS tho lun phn ng trng hp l: xt phn ng: n CH2=CH CH=CH2 t o ,p xt n CH2= CH CH= CH2 t o ,p (CH2CH= CH CH2)n xt xt n CH2= C CH = CH2 n CH = C CH= CH t o ,p o
2 2
t ,p

CH3 GV b sung:
32

(CH2 C =CH CH2)n CH3 poliisopren

 Sn phm trng hp ca buta-1,3-ien v isopren c gi l cao su (cao su l cht hu c c tnh n hi), c tnh cht gn ging cao su t nhin. Tng t anken: ankaien cng lm mt mu dung dch KMnO4.
Hot ng 5 3. iu ch, ng dng ca butaien v isopren
GV su tp mt s hnh nh, mu vt ca cc polime c iu ch t butaien v isopren chiu ln cho HS quan st, yu cu rt ra ng dng ca ankaien v vit cng thc gi tn cc polime trn. HS quan st tho lun. Buta-1,3-ien v isopren l monome quan trng tng hp polime (cao su) c tnh n hi. (CH2C=CHCH2)n cao su isopren CH3

GV hng dn HS nu cc phng php HS butaien v isopren iu ch bng iu ch butaien v isopren. cch tch hiro t ankan tng ng.
xt CH3CH2CH2CH3 to

CH2=CH CH=CH2 + 2H2

xt CH3CHCH2CH3 to

CH3

CH2=C CH=CH2 + 2H2 CH3

Hot ng 6 Cng c bi v bi tp v nh 1. Cng c bi.

GV chiu ln mn hnh cc bi tp sau, HS tho lun: yu cu HS tr li cng c kin thc Phn ng cng H2. hc: Phn ng cng Br2 theo kiu 1,2 v 1. Nu tnh cht ho hc c bn ca kiu 1,4.
33

buta-1,3-ien.

Phn ng trng hp kiu 1,4. Phn ng oxi ho.

2. Vit cng thc cu to v gi tn cc HS tho lun: ankaien c cng thc l C5H8, ch ra CH3CH= CHCH=CH2 (1) cc ankaien lin hp. CH3CH= C=CHCH3 (2)
CH2=CCH=CH2 CH3 CH3C=C=CH2 CH3 (3) (4)

CH2= C=CH CH2CH3 (5) CH2=CHCH2CH=CH2 (6) Ch c (1) v (3) l ankaien lin hp.

2. Bi tp v nh 1, 2, 3, 4, 5, 6 (SGK) D. Hng dn gii bi tp SGk 1. a)

- Polien: L nhng hirocacbon trong phn t c t hai lin kt i tr ln. - ien: L nhng hirocacbon trong phn t c t hai lin kt i tr. - Ankaien: ien mch h c cng thc chung CnH2n2(n 3) gi l ankaien. b) Ankaien c phn chia lm hai loi: Ankaien lin hp v Ankaien khng lin hp. c) Cng thc chung ca ankaien : CnH2n2(n 3). So vi ankan v anken c cng s nguyn t cacbon, ankaien c cng s nguyn t H km ankan 4 nguyn t H, km anken 2 nguyn t H.

2. a) Cng thc cu to v tn gi cc ankaien c cng thc phn t:

- C4H 6 : - C5H8: CH2=C=CHCH2CH3; penta-1,2-ien CH2=CHCH=CHCH3; penta-1,3-ien CH2=CHCH2CH=CH2 penta-1,4-ien CH2 = C = CH CH3 ; buta-1,2-ien CH2 = CH CH = CH2 buta-1,3-ien

34

CH3CH=C=CHCH3; penta-2,3-ien H2C=CH C=C H

CH2= C= CCH3 ; CH3 3-metylbuta-1,2-ien CH3 H d) S ; H2C=CH C=C H e) .

CH2=C=CH=CH2 CH3 2-metylbuta-1,3-ien H CH3

b) ng phn tn ti di dng ng phn hnh hc : penta-1,3-ien:

cis-penta-1,3-ien 3. a) S ;
b) ; c) S ;

trans-penta-1,3-ien

5. a) Cng thc phn t ca A : C5H8.

b) Cc d kin u bi cho cha xc nh cng thc cu to ca A, v c 3 cng thc cu to ph hp: CH2= C CH=CH2 , CH3 C =C =CH2 , CH3 CH3 CH3 CHCCH CH3

6. p s: Khi lng polibutaien thu c l 1580 kg. E. t liu tham kho

Theo quan nim hin nay, trong phn ng cng electrophin vo ankaien, tc nhn electrophin (H+, Br+,) tn cng vo u mang in m ca mch lin hp b phn cc ho v to ra mt cacbocation lin hp.
+

+ 2 3 4

Br

Br

CH2 = CH CH =CH2
1

BrCH2 CH CH = CH2
1 2 3 4

cacbocation ny, in tch dng khng tp trung mt nguyn t C2 m c gii to ra c mch cho ti nguyn t C4 theo s :
Br CH2 CH
+

CH

CH2

V vy, giai on th hai, anion Br c th tn cng vo nguyn t C2 hoc C4, to ra cc sn phm cng 1, 2 v cng 1, 4.

35

(1,2) Br CH2 CH

CH

CH2 +

BrCH2CHBrCH =CH2 BrCH2CH = CHCH2Br

Br (1,4)

Phn ng cng mt tc nhn bt i xng (HCl) vo ankaien bt i xng (isopren) xy ra theo hng ph hp vi s phn b mt electron trong phn t, c th l H+ s tn cng vo u no c mt electron cao hn trong mch lin hp ca phn t: H H C H CH2 = C CH = CH2 CH3 CH3 C CH = CH2 Cl (cng 1,2) + H+ CH3 CH3 C
+

CH

CH2

Cl

CH3 CH3 C = CH CH2 Cl (cng 1,4)

36

Bi 42

khi nim v tecpen

A. Mc tiu bi hc 1. Kin thc

HS bit:

Khi nim v tecpen v c im cu trc ca tecpen. Ngun gc v gi tr ca mt s tecpen n gin khai thc v s dng
hp l ngun tecpen. HS hiu: Chng ct li cun hi nc l mt phng php tch bit quan trng trong phng th nghim v trong sn xut tecpen.

2. K nng

Phn bit c tecpen vi nhng hirocacbon hc. D on c tnh cht ho hc, kim tra v kt lun. Vit phng trnh
ho hc biu din tnh cht ho hc ca tecpen.

3. Tnh cm, thi

Vic gn l thuyt vi thc tin, c bit gi tr v ng dng ca tecpen, lm nhen nhm trong HS tinh thn ham tm hiu nghin cu thin nhin.

B. chun b ca GV v HS

GV:

My tnh, my chiu, cc phiu hc tp. Tranh v hnh 6.7 SGK.

HS: Chun b kin thc bi tecpen.

37

C. tin trnh dy hc Hot ng ca GV Hot ng 1 Kim tra bi c

GV gi 2 HS ln bng trnh by cc ni dung sau, cc HS chun b nhn xt v b sung : 1. Ankaien c phn loi nh th HS 1: no? mi loi cho mt th d. C th chia Ankaien thnh 3 loi Ankaien c 2 lin kt i cnh nhau. V d: CH2=CH=CH2 Ankaien c hai lin kt i cch nhau 1 lin kt n (ankaien lin hp). V d: CH2= CHCH =CH2

Hot ng ca HS

Ankaien c 2 lin kt i cch xa nhau.

V d: CH2= CHCH2CH =CH2 2. Khi cho buta-1,3-ien tc dng vi HS 2 chn p n ng. dung dch HBr (1:1), 800C sn phm chnh thu c l: A. 3-brombut-1-en. B. 1-brombut-2-en. C. 2,3-ibrombutan. D. 1,4-ibrombutan.

p n A.

I- Thnh phn, cu to v dn xut Hot ng 2 1. Thnh phn

GV chiu ln mn hnh hnh 6.7 SGK HS quan st tho lun. (hoc tranh v hnh 6.7 SGK) cho HS quan st.
38

Tinh du thng, s, qu, chanh, cam -tecpinen, -tecpinen, C10H16: -pinen. C15H24: -ceren, -ceren, -selinen. C40H56: caroten, licopen. Yu cu HS nhn xt: Cng thc chung ca tecpen.

Thnh phn phn t. Khi nim tecpen.

Cng thc chung (C5H8)n n2. Gm c C, H l hirocacbon khng no Tecpen l hirocacbon khng no thng
c cng thc chung l: (C5H8)n n2.

2. Cu to
GV vit cng thc cu to ca mt s tecpen. HS quan st tho lun.

miaxen

oximen

limonen

caren

-pinen

-pinen

39

 caroten (mu vng, trong c c rt).

licopen (mu , trong qu c chua). yu cu HS nhn xt c im cu to Phn t tecpen c cu to mch h ca cc tecpen trn. hoc vng v c cha cc lin kt i C=C.

3. Mt vi dn xut cha oxi ca tecpen

GV gii thiu mt dn xut vi cha HS tho lun v nhn xt. oxi ca tecpen, yu cu HS nhn xt v c im cu to v ng dng? Loi mch h:
ch2oh
ch 2 o h

Cu to mch h khng no trong phn t c mt nhm OH. ng dng l nhng n hng qu dng trong cng nghip hng liu v thc phm.

geraniol

xitronelol

Geraniol c trong tinh du hoa hng. Xitronelol c trong tinh du s.

oh

Cu to mch vng c cha oxi. ng dng trong cng nghip thc phm Mentol v menton c trong tinh du bc h. v dc phm.
mentol menton Mt s dn xut khc.

40

cho
cho

geranial

xitronelal
ch2oh

retinol (vitamin A, C20H29OH ).

c h2 o h

phitol dng este c trong dip lc.

IIngun tecpen thin nhin Hot ng 3 1. Ngun tecpen thin nhin

GV yu cu HS nghin cu SGK v tr HS tho lun. li cc vn sau:

Tecpen c u?

Nu cng thc phn t mt s tecpen + Tecpen cng thc C10H16, C15H24 c thng dng. trong qu, l v nha loi thng.
+ Squalen C30H50 c trong du gan c. + Caroten v licopen C40H56 l sc t mu ca c rt v c chua chn.

Tecpen v dn xut c cha oxi ca tecpen thng gp trong gii thc vt. Chng c trong l, thn, hoa, qu hoc r. Ngoi ra cn c trong c th ng vt.

+ Retinol (vitaminA: C20H29OH) c trong lng trng v du gan c

41

2. Khai thc tecpen

GV gii thiu: Phng php hay dng HS quan st. khai thc tecpen l phng php chng ct li cun hi nc (hnh 6.8 SGK).

HS: Tecpen v dn xut cha oxi (tinh du) c thnh phn chnh l GV hng dn HS phn tch c im hirocacbon nn hu nh khng tan cu to ca tecpen, t gii thch ti trong nc, nh hn nc v c nhit sao li hay dng phng php chng si tng i thp d bay hi. ct li cun hi nc. GV b sung: Chng ct li cun hi nc l mt phng php tch bit quan trng trong phng th nghim v trong sn xut. GV gii thiu mt s c s sn xut tinh du trong nc ta.

3. ng dng
GV su tp mu vt, tranh, nh mt s HS quan st (hoc nghin cu SGK). ng dng c bn ca tecpen. Chiu ln mn hnh cho HS quan st (hoc cho HS nghin cu SGK). Tecpen c ng dng: Yu cu HS khi qut ng dng ca Lm hng liu trong cng nghip m tecpen. phm.

Lm nguyn liu trong cng nghip thc phm.

42

 Tecpen v dn xut ca tecpen cn dng sn xut dc phm.

Hot ng 4 Cng c bi v bi tp v nh 1. Cng c bi
GV khc su kin thc cho HS v:

c im cu to ca tecpen v dn xut ca tecpen .

Mch h hoc mch vng. C cha cc lin kt i trong phn t.

ng dng ca tecpen v dn xut ca tecpen.
C ng dng quan trng trong cng nghip: m phm, thc phm, dc phm.

2. Bi tp v nh 2, 3, 4, 5, 6 (SGK) D. Hng dn gii bi tp SGK 2. Cng thc ca oximen v limonen

oximen

limonen

3. Do cng thc phn t oximen v limonen c 10 nguyn t C nn iu kin thng oximen v limonen trng thi lng, t tan trong nc, tan trong mt s dung mi hu c. tch chng c th dng phng php chng ct li cun hi nc. 4. a) S ;
d) ; h) S ; b) S ; e) ; i) ; c) ; g) S ; k) .

43

5. Phng trnh ha hc l:
Ni

+ 2H2(d)

Br + 2Br2(d) Br Br Br

CH2OH

+ Na

CH2ONa

+ 1/2 H2

CH2OH

+ Br2

CH2OH Br Br

44

Bi 43
A. Mc tiu bi hc 1. Kin thc
HS bit:

ankin

Khi nim, cng thc chung ca dy ng ng ankin, bit phn loi v gi tn mt s ankin n gin. Cu to, tnh cht ho hoc c trng ca ankin, iu ch v mt s ng dng ca ankin. Cch phn bit ankan, anken vi ankin bng phng php ho hc.
HS hiu: Nguyn nhn gy ra phn ng th ion kim loi, phn ng trng hp v phn oxi ho khng hon ton l do cu to ca phn t ankin c lin kt ba (gm 2 lin kt v mt lin kt ).

2. K nng

Quan st th nghim, m hnh phn t ankin, rt ra nhn xt v cu to, tnh cht ca ankin. T cng thc bit gi tn v ngc li t gi tn vit c cng thc nhng ankin n gin. Vit phng trnh ho hc minh ho tnh cht ho hc ca ankin.
3. Tnh cm, thi
Ankin c nhiu phn ng mi l, v vy vic nghin cu ankin to cho HS nim hng th trong hc tp, kch thch s sng to.

B. chun b ca GV v HS

GV:

My tnh, my chiu, cc phiu hc tp. M hnh phn t axetilen. Ho cht: CaC2, nc brom, dung dch AgNO3, dung dch KMnO4, dung dch NH3, nc ct.
45

 Dng c: ng nghim, nt cao su km ng dn kh, kp ng nghim, n cn v b gi th nghim. HS: n tp kin thc v anken v xem trc bi ankin.
C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I. ng ng, ng phn, danh php, tnh cht vt l v cu trc Hot ng 1 1. ng ng, ng phn, danh php
GV chiu cng thc cu to thu gn ca mt s ankin ln mn hnh v yu cu HS nhn xt rt ra khi nim ankin. CHCH; CH3CCH; CH3CCCH3 HS quan st, tho lun v nhn xt.

c im chung ca cc hp cht l c mt ni ba trong phn t. Ankin l hirocacbon khng no mch h, trong phn t c cha mt lin kt ba.
C2H2; C3H4; C4H6 CnH2n2 (n 2)

GV t ra cc vn sau yu cu HS HS tho lun. tr li: Anken c cc kiu ng phn cu Anken c nhng kiu ng phn cu to : to no? + ng phn mch C.

Tng t anken yu cu HS nu cc kiu + ng phn v t lin kt i. ng phn ca ankin. Ging anken l ankin c ng phn cu to nhng khng c ng phn cis - trans.
GV yu cu HS vit cng thc ng phn C5H8: ca ankin c cng thc C5H8. CH3CH2 CH2CCH CH3CH2 CC CH3 CH3CH CCH CH3

46

GV chiu ln mn hnh bi tp. HS tho lun, tr li: Quan h s ng phn cu to ca anken C5H10 (x) v ankin C5H8 (y) l A. x > y C. x = y B. x < y D. C 3 trng hp trn p n A.

GV chiu ln mn hnh cng thc cu HS tho lun a ra kt qu: to v tn gi thng thng mt s ankin sau: CH CH, CH3CCH CH3CCCH3 ,CH3CH2CCCH3 CH CH CH3 C CH CH3 C C CH3 axetilen metylaxetilen imetylaxetilen

CH3CH2CCCH3 etylmetylaxetilen Yu cu HS rt ra quy tc gi tn thng Tn thng thng: thng ca cc ankin v gi tn cc + Tn gc ankyl lin kt vi nguyn t ankin c cng thc C5H8. C ca lin kt ba + axetilen. (Cc gc ankyl c gi l theo th t ch ci u tin ca tn gi chng). HS vit ng phn v gi tn. CH3CCCH2CH3 etylmetyl axetilen CH3CH2CH2CCH propylaxetilen CH3CHCCH CH3 isopropylaxetilen GV chiu ln mn hnh bng 6.2 SGK cho HS quan st (hoc c th cho HS nghin cu bng 6.2 SGK). Yu cu HS: HS quan st tho lun. Nu quy tc gi tn thay th ca Quy tc: S ch v tr nhnh + tn nhnh + tn mch chnh + s ch v tr lin kt ankin. ba + in Cch chn mch chnh.
47

 Chn mch C di nht c cha lin kt ba. Cch nh s. nh s th t t pha gn lin kt n Cch ghi ch s lin kt ba. S ch v tr lin kt ba ghi ngay trc ui in. Yu cu HS gi tn cc ankin c cng HS vit ng phn v gi tn: thc C6H10 CH3CH2CH2CH2 CCH hex-1-in
CH3CH2CH2CCCH3 CH3CH2CCCH2CH3 hex-2-in hex-3-in

CH3CHCH2CCH 4-metylpent-1-in CH3 CH3CHCCCH3 4-metylpent-2-in CH3 CH3CH2CHCCH 4-metylpent-1-in CH3 CH3 CH3 C CCH 3,3-imetylbut-1-in CH3

Hot ng 2 2. Tnh cht vt l

GV chiu bng 6.2 trang 175 ln mn hnh, yu cu HS nhn xt.

Hot ng 3 3. Cu trc phn t

GV chiu m hnh phn t axetilen ln HS tho lun v tr li. mn hnh.

Yu cu HS tho lun:
48

 Vit cng thc electron ca axetilen, Cng thc electron: t nu cu to ca lin kt ba. H : C C : H
H C C H Cu to ca lin kt ba gm hai lin kt v mt lin kt gia. Trng thi lai ho ca C trong lin kt Nguyn t C trng thi lai ho sp. ba, gc lin kt HCC. Gc lin kt HCC l 1800. V tr tng i ca cc nguyn t. Hai nguyn t C v hai nguyn t H cng nm trn ng thng.

Rt ra tnh cht ho hc c th c ca Tnh cht ho hc ca ankin: + Do cu to gm hai lin kt km ankin. bn vng nn ankin c phn ng cng ging anken, ankaien. + Hai lin kt nm trn cng hai nguyn t cacbon lm phn cc lin kt CH nn ank-1-in c phn ng th ion kim loi (hay kim loi).
II. Tnh cht ho hc Hot ng 4 1. Phn ng cng a) Cng hiro
GV yu cu HS phn tch cu to ca HS tho lun v tr li: ankin, kh nng phn ng ca ankin vi H2. Ankin c 2 lin kt km bn c kh nng cng H2 ph v tng lin kt . GV gi HS: phn ng ca ankin vi Khi c xc tc Ni th phn ng xy ra qua 2 giai on: H2 xy ra qua 2 giai on theo s :
Ni CH 2 =CH 2 o Yu cu HS vit phng trnh ho hc CH CH + H2 t minh ho s trn. Giai on 2: to ankan

+ H2 + H2 C2H4 C2 H 6 C2H2 Ni Ni

Giai on 1: to anken

Ni CH3 CH3 CH2 = CH2 + H2 o t

49

GV b sung: Mun phn ng dng giai on 1 th dng xc tc thch hp (Pd/PdCO3 xc tc nhim c gim kh nng xc tc) phn ng dng li giai on 1 to anken. HS vit phng trnh ho hc. GV yu cu HS vit phng trnh ho Pb / PdCO3 CH CH + H2 CH2 = CH2 hc. to GV yu cu HS lp s tng qut ca HS vit s : + H2 + H2 ankin vi hiro v vit phng trnh C H CnH2n CnH2n+2 n 2n 2 Ni Ni ho hc minh ho. Ni CnH2n 2 + H2 CnH2n to
Ni CnH2n + H2 CnH2n+2 to

b) Cng brom
GV lm th nghim: HS quan st tho lun. Cho vi mu nh canxicacbua vo ng nghim ng 1ml H2O v y nhanh bng nt c ng dn kh u vut nhn, Hin tng: ban u c kh thot ra, dn kh thot ra vo dung dch Br2. kh lm nht dung dch brom. Yu cu HS nu hin tng v gii Gii thch: Kh thot ra l axetilen thch bng phng trnh ho hc. phn ng vi dung dch Br2 theo hai giai on lin tip. CH CH + Br2 CH = CH Br Br 1,2-ibrometen CH = CH + Br2  Br CH CH Br Br GV b sung: Giai on sau xy ra kh hn giai on trc. Ni chung ankin lm mt mu dung dch brom chm hn anken. Br Br Br 1,1,2,2-tetrabrometan

50

c) Cng hiroclorua
GV yu cu HS: HS tho lun.

Vit cc phng trnh ho hc ca + Ankin cng HX xy ra qua 2 giai ankin vi HCl. on lin tip.
o xt ,t GV gi : Phn ng ny cng xy ra CH CH + HCl CH2 = CHCl qua hai giai on v giai on sau kh vinyl clorua khn hn giai on trc. o xt,t CH2 =CHCl + HCl CH3 CHCl2

1,1-icloetan + Khi c xc tc thch hp ankin tc GV hng dn HS vit phng trnh dng vi HCl sinh ra dn xut ho hc ca axetilen vi HCl. monoclo ca anken.
HgCl2 CHCH+HCl o CH2 = CHCl 150 200 C

So snh vi phn ng cng Br2, H2 cho v d minh ho?

+ Khc vi cng H2, Br2. Ankin bt i cng HX tun theo quy tc Maccp-nhi-cp CH3 CCH + HCl CH3 C =CH2 Cl CH3CH=CH2+ HClCH3CCl2CH3 2,2-icloetan

d) Cng nc (hirat ho)

HS lng nghe v vit phng trnh ho Khi c mt HgSO4 trong mi trng axit hc. th ankin c th cng H2O to ra hp cht trung gian khng bn v chuyn thnh anehit hoc xeton. GV gii thiu cho HS bit:

Phn ng cng nc cng xy ra theo quy tc Mac-cp-nhi-cp.

GV yu cu HS vit phng trnh ho hc ca etin v propin vi nc.

HgSO4 ,H2SO4 CHCH+H2O [CH2=CHOH] o 80 C

khng bn CH3CHO
51

CH3 CH3CCH+H2O [CH2=COH]

HgSO4 ,H2SO4 o 80 C

khng bn CH3COCH3 GV hng dn HS nhn xt phn ng HS nhn xt: Phn ng cng hp vi cng hp ca ankin vi nc so vi nc ch xy ra vi t l mol (1:1). phn ng cng H2, Br2, HCl.

e) Phn ng ime v trime ho

GV hng dn HS vit phng trnh HS tho lun v vit phng trnh ho ho hc: xem axetilen (HCCH) nh hc:

mt HX v yu cu HS vit phng Hai phn t axetilen cng hp. trnh ho hc ime v trime ca xt,t o CHCH + HCCH axetilen. CH2=CHC CH vinylaxetilen Ba phn t axetilen cng hp.
C,600 C 3C2H2 C6 H 6 ( o

) benzen

Hot ng 5 2. Phn ng th bng ion kim loi

GV lm th nghim: Sc kh axetilen HS quan st v nhn xt. vo dung dch AgNO3 trong dung dch NH3 ( c chun b sn: Nh t t dung dch AgNO3 vo dung dch NH3 v lc n khi dung dch trong sut). Hin tng: C kt ta mu vng xut GV yu cu HS: Quan st v nu hin hin. tng. HS tham gia gii quyt vn : GV nu vn : So vi ank-1-in th ank-2-in khng c hin tng g xy ra, ti sao li c s khc nhau nh vy? GV hng dn, iu khin HS gii
52

 So vi ank-1-in th ank-2-in khng So snh s phn cc lin kt CH c H lin kt vi CC. trong C ni ba vi cc lin kt CH Lin kt CH ca( CCH) b phn khc. cc mnh nht do lin kt ba tp trung Kh nng phn ng ca H lin kt mt eletron cao nht. CC. Do b phn cc mnh nn lin kt Vit phng trnh ho hc minh ho. CH ca ank-1-in phn cc mnh, ng cao d Tng t yu cu HS vit phng trnh nguyn t H c tnh linh + b thay th bi ion bc(Ag ). ho hc cho propin.
HCCH + 2AgNO3 + 2NH3 AgCCAg+ 2NH4NO3 bc axetilua (mu vng) CH3CCH + AgNO3+NH3

quyt vn . Yu cu HS: So snh cu to ca ank-1-in vi ank-2-in.

CH3CCAg+NH4NO3 GV hng dn HS kt lun vn , yu Kt lun: ch c ank-1-in mi c phn cu HS nu ng dng ca phn ng ng ho hc vi AgNO3 to ra kt ta. trn? ng dng tnh cht trn c dng phn bit ank-1-in vi anken, ankaien v ankin khc.

Hot ng 6 3. Phn ng oxi ho a) Phn ng oxi ho hon ton

GV lm th nghim t chy axetilen trong khng kh. Yu cu HS vit phng trnh phn ng chy ca ankin v nhn xt v:

Hin tng. T l s mol H2O v CO2. Nhit lng to ra.

HS quan st, nhn xt.

Axetilen chy cho ngn la mu xanh nht. o 5 t C2H 2 + O 2 2CO2 + H2O 2

53

CnH2n2+

o 3n 1 t O2 nCO2+(n1)H2O 2 n CO2 > n H2O .

Phn ng chy to nhiu nhit.

b) Phn ng oxi ho khng hon ton
GV lm th nghim: Sc kh axetilen HS quan st v tho lun: vo dung dch thuc tm (KMnO4) yu cu HS: Hin tng dung dch thuc tm nht Nu hin tng. mu dn ng thi xut hin kt ta mu nu (MnO2).

Gii thch.

Gii thch ankin c lin kt km bn nn phn ng vi KMnO4 ging anken v ankaien.

Phng trnh ho hc:

GV hng dn HS vit phng trnh 3CHCH + 8KMnO4 3(COOK)2 + 2KOH ho hc (minh ho). + 8MnO2+ 2H2O GV nhn xt: Phn ng lm mt mu dung dch thuc tm c th dng nhn bit cc ankin. So vi anken phn ng ny xy ra chm hn.

III. iu ch v ng dng Hot ng 7 1. iu ch

GV gii thiu: Phng php iu ch HS: Axetilen c sn xut ch yu t axetilen trong cng nghip l nhit metan. o 1500 C phn mtan 15000C, yu cu HS vit 2CH C2H2+ 3H2 4 phng trnh ho hc. GV b sung: Ngoi ra ngi ta cn iu HS vit phng trnh ho hc: o 900 C ch C2H2 t than v vi. CaCO3 CaO + CO2 l in GV hng dn HS vit phng trnh CaO + 3C CaC2 + CO ho hc iu ch t n.
54

GV lm th nghim iu ch axetilen t t n CaC2: Cho vo trong bnh tam gic mt t t n CaC2, trong bnh c cha sn mt t nc. y nhanh bng nt cao su c gn ng thu tinh vut nhn, cho HS quan st v th mt s tnh cht vt l. GV yu cu HS: Vit phng trnh phn ng. HS quan st v tho lun: Phng trnh ho hc. Kh thot ra c tnh cht g (mu, CaC2 + 2H2O Ca(OH)2 + C2H2 mi) Gii thch. Kh thot ra khng mu, c mi

Gii thch kh thot ra c mi do t n c ln nhiu tp cht ca lu GV b sung: Phng php iu ch cc cht t than v vi ngy nay t hunh, nit nn to ra kh c mi nh H2S, NH3. c dng v khng kinh t.
2. ng dng
GV: t tnh cht ho hc ca ankin, yu HS tho lun: cu HS nu ng dng. Axetilen chy to nhiu nhit nn c dng lm nhin liu. V d: n x oxi-axetilen dng hn, ct kim loi. Mt s thit b to ngn la cho nhit cao. Cc phn ng cng, trime, ime v GV: C th su tp tranh nh, mu vt chiu ln mn hnh cho HS quan st, trng hp c ng dng trong qu trnh tng hp cc hp cht hu c. lm phong ph ng dng ca axetilen.

Hot ng 8 Cng c bi v bi tp v nh 1. Cng c bi

GV: Chia HS thnh 4 nhm pht cc phiu hc tp c cc ni dung sau:

55

Phiu 1: t chy hon ton 3 ankin A. B. C thu c 3,36 lt CO2 (ktc) v 1,8 gam H2O. Vy tng s mol ca 3 ankin l:
A. 0,15 B. 0,25 C. 0,08 D. 0,05

p n D. Phiu 2: Bng phng php ho hc. Hy phn bit etan, etilen v axetilen.
HS tho lun:

Dn c ba kh vo dung dch AgNO3/NH3, kh no to kt ta mu vng th kh l C2H2. Dn hai kh cn li qua dung dch brom, kh lm nht mu dung dch brom l C2H4. Cn li l etan.
Phiu 3: Cht hu c X c cng thc phn t C6H6 mch h khng phn nhnh. Bit 1 mol X tc dng vi AgNO3/NH3 d to ra 292 gam kt ta. X c cng thc cu to no di y.
A. CHCCCCH2CH3 C. CHCCH2CCCH3 B. CHCCH2CH=C=CH2 D. CHCCH2CH2CCH

p n D. Phiu 4: Trong mt bnh kn cha hirocacbon X v hiro, nung nng bnh n khi phn ng hon ton thu c ankan duy nht. cng nhit , p sut trong bnh trc khi nung gp ba ln p sut trong bnh sau khi nung. t chy mt lng Y thu c 8,8 g CO2 v 5,4 g H2O. Cng thc phn t ca X l:
A. C2H2 B. C2H4 C. C4H 6 D. C3H4

p n A. 2. Bi tp v nh 1, 2, 3, 4, 5, 6 (SGK) D. hng dn gii bi tp SGK 1. nh ngha sai: A, B, C; nh ngha ng : D, E. 2. Cc cng thc cu to ca hirocacbon mch h vi cng thc C5H8.
CHCCH2CH2CH3; (A) pent-1-in CH3CCCH2CH3 ; (B) pent-2-in CHCCHCH3 CH3 (C) 3-metylbut-1-in

56

CH2=C=CHCH2CH3; CH2=CHCH=CHCH3; (D) penta-1,2-ien CH3CH =C=CH CH3 ; (G) penta-2,3-ien (E) penta-1,3-ien CH2=CCH=CH2

CH2=CHCH2CH=CH2 (F) penta-1,4-ien CH3C=C=CH2

CH3 (H) 2-metylbuta-1,3-ien

CH3 (I) 3-metylbuta-1,2-ien

(A) v (B) l ng phn v tr lin kt ba. (A) v (C), (B) v (C) l ng phn mch cacbon. (D), (E), (F), (G) cng nh (H), (I) l ng phn v tr lin kt i. (D), (E), (F), (G) l ng phn mch cacbon vi (H) v (I). (A), (B), (C) v (D), (E), (F), (G), (H), (I) l ng phn nhm chc. 3. Cc phng trnh ho hc:
Ni,t a) CH3 C CH + 2H2 CH3 CH2 CH3 o

Pd / PbCO3 CH3 CH = CH2 b) CH3 C CH + H2 CCl 4 c) CH3 C CH + Br2 CH3CBr =CHBr 20o C

CCl 4 d) CH3 C CH + 2Br2 CH3 CBr2 CHBr2 20o C

H2 O e) CH3 C CH + AgNO3 + NH3 CH3 CCAg + NH4NO3

Hg / H h) CH3 C CH + HOH CH3 C CH3 2+

g) CH3 C CH + 2HCl(k) CH3 CCl2CH3

+

4. a) Dng dung dch AgNO3 /NH3 nhn ra C2H2: C kt ta mu vng nht. Dng nc brom nhn ra C2H4 ( lm mt mu nc Br2), cn li l etan.
b) Dng dung dch AgNO3/NH3 nhn ra but-1-in (c kt ta vng nht), cn li l butaien. c) Dng dung dch AgNO3 /NH3 nhn ra but-1-in (c kt ta vng nht), cn li l but-2-in.

5. a) Phng php i t CH4 c dng nhiu v CH4 c nhiu trong kh thin nhin v sn phm ch bin du m, cn phng php i t vi tn nng lng nhiu hn, cho kh axetilen c ln nhiu tp kh (H2S, NH3, PH3 ) l nhng kh c c hi, gi thnh cao hn.

57

b)

+ HCl CHCH CH2=CHCl o 150 200 C,xt HgCl 2

5000C

HCl

+ Cl2 CH2=CH2 CH2Cl CH2Cl

c) Phng php i t etilen cho sn phm r hn v CH2 = CH2 c sn trong kh crackinh cn CHCH phi iu ch t CH4 15000C tn nng lng nn t hn.

6. Phng trnh ho hc:

2CH4
1500 C CH CH + 3H2
o

(1) (2)

HCCH + 2[Ag(NH3 )2]OH AgCCAg + 2H2O + 4NH3

a) Theo phng trnh ho hc (1) nu gi s mol C2H2 sinh ra l x th : 3,36 S mol hn hp kh sau phn ng nhit phn l : + 2x = 0,15 + 2x 22,4 Theo u bi th tch hn hp gim 20% l th tch C2H2 : tnh ra c x = 0,05 mol. Nu phn ng t hiu sut 100% th s mol C2H2 l phn ng nhit phn l: b) % VC2 H2 = 20% ; 0,05.100% 66,67% 0,075
VH2 = 60% ;

x.100% = 20% 2x + 0,15

0,15 mol. Vy hiu sut 2

% VCH4 = 20%

c) Cho hn hp qua dung dch AgNO3/NH3 d, thu ly dung dch ri cho phn ng vi dung dch H2SO4 long d, thu c C2H2.

58

e. t liu tham kho S iu ch cc sn phm cng nghip t Axetilen

polivinyl axetat CH2=CH OCOCH3
polivinylclorua (PVC)

polivinyl ete

axit axetic C2H5OH

etyl axetat

CH2=CHOR

CH3CHO

CH3CHCH2-CH2 OH OH CH2=CHCH=CH2 buta-1,3-ien

CH2=CHCl CH2=CHCN polivinylnitrin CH2=CHCOX (X= OH, OR, -NH2)

axit acrylic v dn xut

CH CH axetilen

CH2=CHC CH

cao su Buna

CH2=CHCOCH3 vinylmetyl xeton ( CH=CH )n polien CH2-CH CH-CH2 OH OH Cl2CHCHCl2 tetracloetan

HOCH2CH2CH2CH2OH buta-1,4-iol axit sucxinic HOOC-(CH2)4-COOH axit aipic NC-CH2CH2CH2CH2-CN aipo nitrin O tetra hiro furan

Nilon-6,6

H2N-(CH2)6-NH2 hexametylen iamin

59

Bi 44

luyn tp Hirocacbon khng no

A. Mc tiu bi hc 1. Kin thc

HS bit:

S ging nhau v khc nhau v tnh cht gia anken, ankin v ankaien. Cch phn bit ankan, anken, ankaien bng phng php ho hc.
HS hiu:

Mi lin quan gia cu trc, tnh cht ho hc c trng ca hirocacbon khng no v phng php iu ch ca anken, ankin v ankaien.
2. K nng

T cng thc cu to bit gi tn v ngc li t tn gi vit c cng

thc cu to ca nhng anken, ankin, ankaien n gin.

Rn luyn k nng so snh, tm mi lin h gia thc c bn gia anken,

ankin v ankaien t c cch nh h thng.

Vn dng kin thc hc t bit cch gii ng bi tp.

B. chun b ca GV v HS

GV:

My tnh, my chiu, cc phiu hc tp, h thng bi tp n tp. Bng s chuyn ho gia ankan, anken ankin v ankaien.

HS: n tp cc kin thc l thuyt, phng php gii bi tp v anken,

ankaien, ankin.

60

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I Kin thc cn nm vng Hot ng 1 1. Cu trc

GV nu cc vn c bn hc:

Khi nim anken, ankaien, ankin. c im cu trc lin kt ca anken ankaien, ankin. Tnh cht ho hc c bn ca hirocacbon khng no. Phng php iu ch v ng dng ca anken, ankaien, ankin.
GV chia HS theo cc nhm (4 nhm) HS tho lun: v giao ni dung luyn tp cho cc Anken nhm. 1. CTTQ CnH2n (n 2, n N* ) GV: yu cu HS (nhm 1) nu cng 2. Cu trc nguyn t C ca lin kt thc tng qut v cu trc ca anken, i trng thi lai ho sp2. Cc ankaien, ankin. nguyn t lin kt vi C ni i nm trn cng mt mt phng. R1 C=C R2 R4 CnH2n2 (n 3, n N* ) R3

Ankaien
1. CTTQ 2. Cu trc 4 nguyn t C ca lin kt i trng thi lai ho sp2. Cc nguyn t lin kt vi C ni i nm trn cng mt mt phng.

61

R1 C=C R2 R4

R3 R6 C=C R5

Ankin
1. CTTQ CnH2n2 (n 2, n N* )

2. Cu trc nguyn t C ca lin kt ba trng thi lai ho sp. Cc nguyn t lin kt vi C ni ba nm trn cng ng thng. R1 C C R2

2. Tnh cht vt l GV yu cu HS (nhm 2) nu tnh cht HS tho lun. vt l ca cc hirocacbon khng no, T C2 C4 th kh, t C5 tr i quy lut bin i t0s, t0nc. th lng hoc rn. Hirocacbon l hp cht khng mu, khng tan trong nc, nh hn nc. t0s, t0nc tng dn khi s nguyn t C tng. Anken, ankin, ankaien khng c mi, cn tecpen c mi c trng. 3. Tnh cht ho hc
GV yu cu HS (nhm 3) nu tnh cht ho hc ca cc hirocacbon khng no, so snh kh nng cng brom ca anken v ankin. HS tho lun. a) Phn ng cng: Cng hiro khi c xc tc (Ni, Pt, Pd) v nhit thch hp th u b hiro ho thnh ankan tng ng. Ring ankin phn ng cng xy ra theo hai giai on, mun phn ng dng giai on 1 th dng xc Pd/PbCO3, sn phm l anken. Cng halogen u lm mt mu dung dch brom v b halogen ho thnh dn xut i hoc tetra halogen.

62

Tc cng brom ca anken nhanh hn ankin khong nm ln, ankin c kh nng cng nhiu brom hn anken.

Cng HX theo quy tc Mac-cp-nhicp: hirocacbon khng no c kh nng cng HX phn ng cng th hng tn cng ca X vo C ni i, ni ba c bc cao hn s l sn phm chnh. Ankaien cng theo kiu 1,2 v 1,4.
b) Trng hp: Khi c xc tc ph hp v c nhit , p sut th anken v ankaien u dy u d trng hp thnh polime, ankin khng b trng hp m ch b ime ho, trime ho c) Oxi ho: tt c u lm mt mu dung dch thuc tm; Chy mnh v to nhiu nhit n CO2 n H2 O d) Ring ank-1-in c phn ng th nguyn t H ca C ni ba bng ion bc. GV yu cu HS (nhm 4) nu phng HS tho lun v tr li. php iu ch v ng dng ca cc a) iu ch: hirocacbon khng no. Trong cng nghip sn xut anken, ankin v ankaien ch yu t ankan du m. Trong phng th nghim axetilen c iu ch t t n (CaC2). Cn etilen c iu ch t ancol etylic. b) ng dng: Anken, ankaien ch yu dng sn xut polime lm cht do, cao su. Anken v ankin c dng lm nguyn liu sn xut cc dn xut ca hirocacbon. Ankin cn c s dng l nhin liu n x.

63

Hot ng 2 II. Bi tp
GV chiu bi tp 1 (SGK) ln mn hnh HS tho lun. 1. a) Hy in tip cc s thch hp vo bng sau:
Cng Hirocacbon Ankan Monoxicloankan Anken Ankin Ankaien Oximen( ) Limonen( )
* *

S nguyn t H t hn ankan tng ng 0 2

thc phn t CnH2n+2 CnH2n CnH2n CnH2n2 CnH2n2 CnH2n2 C10H16

S lin kt pi () 0 0

S vng (v) 0 1

Tng s ( + v) 0 1

(**) Dng k hiu ( + v) trong cc bi tp s c li v gn b) Hy cho bit s lng nguyn t H phn t xicloankan v phn t mi loi hirocacbon khng no t hn phn t ankan tng ng l bao nhiu, gii thch v sao li t hn ngn y . HS tho lun v a ra kt qu: 1. a)
Cng Hirocacbon thc phn t Ankan Monoxicloankan Anken Ankin Ankaien Oximen(*) Limonen( )
*

S nguyn t H t hn ankan tng ng 0 2 2 4 4 6 6

S lin kt pi () 0 0 1 2 2 3 2

S vng (v) 0 1 0 0 0 0 1

Tng s ( + v) 0 1 1 2 2 3 3

CnH2n+2 CnH2n CnH2n CnH2n2 CnH2n2 CnH2n2 C10H16

64

b) S nguyn t H xicloankan t hn ankan 2 nguyn t v xicloankan c 1 vng no, anken c s nguyn t H t hn ankan v anken c 1 lin kt . Ankin, ankaien c s nguyn t H t hn ankan 4 nguyn t v chng c 2 lin kt . GV chiu bi tp 2 (SGK) ln mn hnh HS tho lun. 2. Hy in cc t hoc cc s cho di y vo ch trng trong cc cu sau: a) Anken v(1)u c ( + v) = 1, nhng(2)c (v) = 1 cn ( 3)c (v) = (4) b) (5)v(6)u c ( + v) = 2, chng u c =(7)v (v)= (8) A: ankin; B: 1; C: xicloankan; D: 2; E: anken; G: ankaien, H: 2, K: 0 HS tho lun v a ra kt qu: a) (1) xicloankan (2) xicloankan (3) anken (4) 0 b) (5) ankanien (6) ankin (7) 2 (8) 0 GV chiu bi tp 3 (SGK) ln mn hnh HS tho lun. 3. a) Menton (mi bc h) c cng thc phn t C10H18O, ch cha 1 lin kt i. Hi n c cu to mch h hay mch vng? b) Vitamin A cng thc phn t C20H30O, ch cha 1vng 6 cnh khng cha lin kt ba. Hi trong phn t c my lin kt i? HS tho lun v a ra kt qu: a) Menton c CTPTC C10H18O c + v = 2.20 + 2 18 = 2( + v = 2; = 1 v 2

v = 1) .

b) CTPTca vitamin A l C20H30O c 2.20 + 2 30 + v= = 6.( + v= 6; v=1 = 5), khng c lin kt ba, vy s 2 lin kt i l 5. GV chiu bi tp 4 (SGK) ln mn hnh HS tho lun. 4. a) Hy vit cng thc cu to chung ca anken, ankaien, ankin v nu c im trong cu trc khng gian ca chng. b) Hy cho bit nhng nhm nguyn t no quyt nh c tnh ho hc ca anken, ankaien, ankin. V sao ?
65

c) Hy nu nhng phn ng c trng ca anken, anka-1,3-ien v ankin. HS tho lun v a ra kt qu: a) Cng thc chung ca anken, ankaien, ankin. Anken CnH2n (n 2) c im cu trc khng gian cc nguyn t lin kt trc tip vi C=C u nm trn mt mt phng v gc lin kt 1200.

Ankin CnH2n2 (n 2) c im cu trc khng gian cc nguyn t lin kt trc tip vi CC u nm trn mt ng thng v gc lin kt bng 1800 Ankaien CnH2n2 (n 3) c im cu trc khng gian tu thuc vo v t tng i ca cc lin kt i nu hai ni i cch xa nhau th cc nguyn t lin kt trc tip vi C=C u nm trn mt mt phng v gc lin kt 1200.
b) Nhm nguyn t quyt nh tnh cht ca anken, ankaien, ankin l nhm: C=C v CC bi v cc nhm c mang lin kt km bn nn l trung tm ca cc phn ng ho hc. c) Phn ng c trng ca anken, anka-1,3-ien, ankin l phn ng cng (H2, Br2, HX) phn ng oxi ho khng hon ton. Ring ank-1-in c phn ng th bi ion bc to ra kt ta mu vng.

Anka-1,3-ien c phn ng cng 1,2 v cng 1,4.

GV chiu bi tp 5 (SGK) ln mn hnh HS tho lun. 5. a) Hy nu nguyn tc chung iu ch anken, ankeien, ankin dng trong cng nghip tng hp hu c. Ly v d iu ch cht tiu biu cho mi loi. b) V sao etilen l ho cht hu c c sn xut vi sn lng ln nht ? HS tho lun v a ra kt qu: a) Nguyn tc chung iu ch anken, ankaien, ankin l tch hiro ra khi ankan. Th d iu ch cht tiu biu: xem SGK. b) Etilen ngy nay c dng lm nguyn liu quan trng trong sn xut polime (PE, PVC) v nhiu ho cht c bn khc (nh etanol, axetanehit ) nn c sn xut vi sn lng ln nht. GV chiu bi tp 6 (SGK) ln mn hnh HS tho lun. 6. Dng cng thc cu to hy vit phng trnh ho hc ca phn ng theo s sau: + Br2 C C4H6Br2 (mt cht) 0 t ,xt A + Br2 t0 ,xt - H2 D C4H6Br2 (hai cht) C4H10 0 - H2 t xt , B + AgNO3, NH3 - H2 E kt ta
66

HS tho lun v a ra kt qu:

t ,xt CH3CH=CHCH3 + H2 (A) CH3CH2CH2CH3
o

t ,xt CH3CH2CH2CH3 CH2=CHCH2CH3 + H2 (B)

o

t ,xt CH3CH=CHCH3 H2 + CH3CCCH3

o

(C) (D) (D) (E)

CH3CH=CHCH3 H2 + CH2=CHCH=CH2
t o ,xt

CH2=CHCH2CH3 H2 + CH2=CHCH=CH2
t o ,xt

CH2=CHCH2CH3 H2 + CH2CCH2CH3
t o ,xt

CH3 CCCH3 + Br2 CH3CBr=CBrCH3 CH2 CH CH = CH2 CH2 =CHCH =CH2 + Br2 Br Br CH2 CH CH = CH2 Br Br HCCCH2CH3 + AgNO3 + NH3 AgCCCH2CH3 + NH4NO3 GV chiu bi tp 7 (SGK) ln mn hnh HS tho lun. 7. Khi t chy hon ton mt hirocacbon th kh (iu kin thng) th thy th tch cc kh to thnh sau phn ng ng bng th tch cc kh tham gia phn ng ( cng nhit v p sut). Hy cho bit hirocacbon c th nhn nhng cng thc phn t nh th no ? HS tho lun v a ra kt qu: Phng trnh ho hc. o y y t C xH y + ( x + ) O 2 H2O x CO2 + 4 2 y y 1+x+ =x+ y=4 4 2

Vy hirocacbon th kh c th l : CH4 ; C2H4 ; C3H4 ; C4H4. GV chiu bi tp 8 (SGK) ln mn hnh HS tho lun. 8. Hn hp A gm hai cht k tip nhau trong dy ng ng ca etilen. Cho 3,36 lt (ktc) hn hp kh trn phn ng hon ton vi Br2 trong CCl4 th thy khi lng bnh cha nc brom tng thm 7,7 gam. a) Hy xc nh cng thc phn t ca hai anken . b) Vit cng thc cu to ca anken ng phn c cng cng thc vi hai anken cho.
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HS tho lun v a ra kt qu: 3,36 = 0,15 (mol) S mol ca hn hp = 22,4 Gi cng thc chung ca hai anken l :

C n 2n

a) C n 2n + Br2 C n 2 n Br2 Khi lng bnh brom tng chnh l khi lng ca hai anken. 7, 7 = = 5,13 (g/mol) 14 n = 51,3 n = 3,66 0,15
V hai olefin k tip nhau nn CTPT l : C3H6 v C4H8 b) Gi s mol ca C3H6 : a (mol) c M= 42 (g/mol) ; C4H8 : b (mol) c M = 56 (g/mol) ta c h: a + b = 0,15 42a + 56b = 7,7 Gii h phng trnh, c a = 0,05 ; b = 0,1. 0,05.100% % th tch C3H6 = = 33,33% 0,15 % th tch C4H8 = 100% 33,33% = 66,67% c) Cc CTCT c th c ca: C3H6 l : CH2 = CH CH3 C4H8 l : CH2=CHCH2CH3 ;

CH3CH =CHCH3 ;

CH2 =CCH3 CH3

GV chiu bi tp 9 (SGK) ln mn hnh HS tho lun. 9. Nhit phn 2,8 lt (ktc) etan 12000C ri cho mt na hn hp kh thu c sc qua bnh ng nc brom (d) th thy khi lng bnh ny tng ln thm 1,465g. Cho na hn hp kh cn li phn ng vi dung dch AgNO3 trong amoniac th thu c 0.60g kt ta mu vng. Bit rng phn ng nhit phn to ra etilen, axetilen l phn ng khng hon ton, cc phn ng tip sau u xy ra hon ton. Hy xc nh thnh phn phn trm v th tch ca hn hp kh thu c. HS tho lun v a ra kt qu: 2,8 S mol ca C2H6 = = 0,125 (mol) 22,4

68

 Khi nhit phn C2H6 thu c : C2H4 : a (mol) ; C2H2 : b (mol) ;

H2 : (a+2b) mol v C2H6 : d. C2H4 + Br2 C2H4Br2 a a C2H2 + 2Br2 C2H2Br4 b 2b C2H2 + 2AgNO3 + 2NH3 AgCCAg + 2NH4NO3 2.0,6 b= = 0,005 (mol) do : 28a + 26b = 1,465.2 = 2,93 a = 0,1 (mol) 240 n 2 = a + 2b = 0,1 + 0,01 = 0,11

n C2 2 d = 0,125 (a + b) = 0,125 (0,1 + 0,005 ) = 0,01 Tng s mol hn hp kh : 0,1 + 0,005 + 0,11 + 0,02 = 0,235 0,1.100% 0,005.100% = 42,55% % n C24 = = 2,13% % n C22 = 0,235 0,235
% n 2 =
0,11.100% = 46,8% 0,235

% n C2 6 = 100% (42,55% + 2,13% + 46,8%) = 8,52%

Bi tp ngh 1. Ankaien sau c bao nhiu ng phn hnh hc.

CH3CH=CHCH=CHCH3 D. Khng c ng phn hnh hc. p n B 2. Hn hp X gm hai anken l ng ng lin tip c t khi so vi H2 bng 19. Tm cng thc phn t cc anken v % th tch mi anken trong hn hp. A. C2H4 28,6% v C3H6 71,4%. B. C2H4 71,4% v C3H6 28,6%. C. C3H6 28,6% v C4H8 71,4%. D. C3H6 71,4% v C4H8 28,6%. p n A 3. t chy hon ton m gam hn hp hai ankin cho ra 13,2 gam CO2 v 3,6 gam H2O. Tnh khi lng brom ti a c th cng vo m gam hn hp trn. A. Khng d kin B. 32 gam C. 16 gam D. 8 gam A. 2 B. 3 C. 4

69

4. Khi hiro ho hon ton licopen C40H56 thu c cht C40H82 cn hiro ho hon ton caroten C40H56 thu c cht C40H78. Hi trong licopen v trong caroten c bao nhiu lin kt i v bao nhiu vng. Bit trong phn t c hai cht ch c lin kt n, lin kt i v vng 6 cnh. A. 13 lin kt i, khng vng; 11 lin kt i, 2 vng. B. 11 lin kt i, khng vng; 13 lin kt i, 1 vng. C. 12 lin kt i, 1 vng; 12 lin kt i, 2 vng.

D. 13 lin kt i, 1 vng;

13 lin kt i, 2 vng.

p n A. 5. t chy hon ton 22,4 lt hn hp kh X gm CO, CH4, C3H6 (ktc) thu c 44,8 lt CO2 (ktc). Tnh % th tch ca C3H6 trong X.

A. 21,9 % C. 32,7 %

B. 25,36 % D. 50 %

p n D. 6. Hirocacbon X tc dng vi dung dch brom d thu c dn xut tetrabrom (cha 4 nguyn t brom) Y. Bit trong Y brom chim 75,82% khi lng. Tm cng thc phn t ca X. A. C7H10 B. C8H6 C. C8H8 D. C9H6 p n B.

70

Bi 45 thc hnh Tnh cht ca hirocacbon khng no

A. Mc tiu bi hc 1. Kin thc

Bit c mc ch, cch tin hnh, k thut tin hnh mt s th nghim c th: iu ch v th tnh cht ca axetilen: Phn ng chy, phn ng vi dung dch brom, vi dung dch AgNO3 trong NH3. Phn ng ca hirocacbon khng no vi nc brom. Cng c tnh cht l ho ca mt s hp cht hu c nh tecpen, axetilen.
2. K nng

S dng dng c, ho cht tin hnh c an ton, thnh cng cc th nghim trn. Quan st, m t hin tng, gii thch, vit cc phng trnh ho hc. Vit tng trnh th nghim.
3. Tnh cm, thi

Bit cch iu ch t s dng hp l ho cht lng nh. Thng qua hot ng th nghim to nn hng th khi hc b mn ho hc.
B. chun b ca GV v HS

GV

My tnh, my chiu, hnh v. Ho cht: + t n.

+ Nc ct.

+ Nc brom. + C chua chn. + Dung dch KMnO4. + Dung dch AgNO3/NH3.

Dng c:

+ ng nghim , n cn. + ng ht nh git. + Nt cao su c lp ng thu tinh vut nhn.

71

+ B gi th nghim. + Ci gi, cc th nghim.

HS: n tp kin thc ca hirocacbon khng no. Xem trc bi thc hnh.

C. tin trnh dy hc Hot ng ca GV Hot ng 1 Dn d trc bui thc hnh GV nu cc ni dung chnh ca bui HS nghe GV trnh by v tho lun thc hnh. theo nhm thc hnh. GV yu cu HS trnh by cc kin thc lin quan n bui thc hnh. Lu HS khi dng ho cht v s dng cn thn cc dng c th nghim. Chia lp hc thnh cc nhm thc hnh mi nhm gm 45 HS. I. Ni dung th nghim v cch tin hnh Hot ng 2 Th nghim 1. iu ch v th tnh cht ca etilen Hot ng 3 Th nghim 2. iu ch v th tnh cht ca axetilen GV: Hng dn HS cc nhm lm th HS lm th nghim theo cc bc: nghim nh SGK. Cho mt vi mu CaC2 bng ht en vo mt ng nghim to c kp cht trn gi st. Rt nc vo ng nghim, y nhanh bng nt cao su c cm ng dn kh. HS quan st thy c kh khng mu GV yu cu HS quan st hin tng v thot ra mnh lit.
72

Hot ng ca HS

gii thch.

Gii thch: Do c phn ng ho hc sau xy ra. CaC2 + 2H2O Ca(OH)2 + C2H2

GV yu cu HS th mt s tnh cht vt l ca kh thot ra: Tnh tan (trong nc). Mi. GV yu cu HS gii thch: Ti sao kh thot ra c mi m theo tnh cht ca axetilen l khng c mi. Cch loi tr cc kh . GV chiu ln mn hnh m hnh mt s dung c iu ch axetilen:

HS tin hnh th tnh cht vt l: Sc kh thot ra vo nc thy kh thot ra hu nh khng tan trong nc. Dng tay vy nh kh thot ra ngi thy kh c mi kh chu (mi kh t n). HS tho lun: Kh axetilen khng c mi, nhng li ln mt s tp cht sinh ra nh H2S, NH3, c trong t n (CaC2). loi tr kh H2S v NH3 ta cho kh i qua dung dch NaOH long. GV hng dn HS tip tc th cc tnh HS tip tc lm th nghim th tnh cht: cht ho hc ca axetilen. Th nghim t chy C2H2: GV yu cu HS nhm 1 lm th nghim + Cho mt vi mu CaC2 bng ht
73

t chy kh C2H2 thot ra. GV lu HS: Axetilen chy to nhiu nhit nn phi lm th nghim vi lng nh ho cht v cn thn khi t kh.

en vo mt ng nghim to c kp cht trn gi st. + Rt nc vo ng nghim. + y nhanh bng nt cao su c cm ng dn kh. + t kh thot ra v a mt s trng li gn ngn la. Hin tng: Axetilen chy vi ngn la sng, to nhiu nhit, to ra CO2 v nc, khi a mt s trng li gn xut hin mui en v cc git nc trn mt s. Gii thch: do c phn ng ho hc: o 5 t C2H2 + O2 2CO2 + H2O (H < 0) 2 Ngoi ra c mt phn C2H2 chy khng hon ton sinh ra C nn lm en mt s v hi nc ngng t to thnh git trn mt s.

HS tin hnh th nghim. GV yu cu HS nhm 3 lm th nghim Th nghim phn ng vi nc brom sc kh qua dung dch brom v dung v dung dch KMnO4. dch KMnO4. HS: Sc t t kh C2H2 iu ch nh th nghim trn vo vo nc brom thy nc brom b nht mu dn, khi sc vo dung dch KMnO4 th thy mu tm ca dung dch nht dn ng thi GV gii thiu: phng trnh ho hc c xut hin kt ta mu nu. ca C2H2 vi KMnO4 (y l phn ng Gii thch: do c phn ng ho hc: ph v lin kt ba to ra cc sn phm C2H2 + Br2 C2H2Br2 phc tp): 1,2-ibrometen 3C2H2 + 8KMnO4 3(COOK)2 + 8MnO2 + KOH + H2O C2H2Br2 + Br2 C2H2Br4 1,1,2,2-tetrabrometan GV yu cu HS nhm 3 lm th nghim HS nhm 3 tin hnh th nghim phn
74

sc kh thot ra vo dung dch AgNO3 ng ca C2H2 vi dung dch trong dung dch NH3. AgNO3/NH3. Dn dng kh qua cc ng nghim ng dung dch AgNO3/NH3 ( chun b sn). Hin tng thy c kt ta mu vng xut hin. Gii thch: Do C2H2 phn ng vi dung dch AgNO3/NH3 to ra kt ta Yu cu HS quan st, c tng nhm HS mu vng (bc axetilua). m t hin tng th nghim v gii HCCH + 2AgNO3 + 2NH3 thch bng phng trnh ho hc. AgCCAg + 2NH4NO3
Hot ng 4 Th nghim 3. phn ng ca hirocacbon khng no vi nc brom GV hng dn HS tin hnh th HS tin hnh th nghim: nghim. Cho vi git du thng vo ng nghim cha 2ml nc brom, lc k, yn vi pht. Hin tng thy nc brom b nht Yu cu HS quan st, nu hin tng mu, nu lu th s mt mu. Gii thch: Du thng l mt tecpen v gii thch. (GV hng dn HS phn tch thnh c trong thin nhin (-pinen C10H16). phn ca du thng gii thch hin Khi phn ng ho hc xy ra cng brom vo ni i ca tecpen c trong tng th nghim). du to thnh dn xut i halogen khng mu.

GV hng dn HS tin hnh th HS tin hnh th nghim: nghim. Ct i qu c chua chn tch b cc ht ra.
Nghin nt phn c chua b ht, lc ly phn nc thu c nc c chua c mu .

GV yu cu HS gii thch hin tng.

Nh t t tng git nc brom (mu nu nht) vo nc c chua (mu ), GV ghi nhn cc kin v b sung lc k, yn thy hin tng dung
75

cch gii thch y ngn gn;

dch chuyn sang mu tm nht.

Nc c chua chn p cng l mt Tip tc nh vi git brom vo lc tecpen (licopen C40H56) trong phn t k, yn thy dung dch chuyn sang c nhiu lin kt i lin hp. mu xanh nht. Khi phn ng ho hc xy ra, Br2 cng vo mt s ni i dn n s ni i lin hp thay i v kt qu mu sc thay i theo. Ngoi tecpen trong nc c chua cn c mt s hp cht khc nh hng n mu ca dung dch.
Hot ng 5 II. Cng vic sau bui thc hnh

GV: Nhn xt v bui thc hnh v HS: thu dn, v sinh phng th nghim hng dn HS thu dn ho cht, ra cn thn, an ton. ng nghim v dng c th nghim, v sinh phng th nghim. GV: Yu cu HS lm tng trnh theo mu. HS lm tng trnh theo mu sau y: Ngy thng.nm. H v tn: Lp:. T th nghim:. Tng trnh ho hc bi s:. Tn bi:
Tn th nghim Phng php tin hnh Hin tng quan st Gii thch vit phng trnh phn ng

76

Chng VII Hirocacbon thm Ngun hirocacbon thin nhin

Bi 46

benzen v ankylbenzen

A. Mc tiu bi hc 1. Kin thc

HS bit:
nh ngha, cng thc chung, c im cu to, ng phn, danh php. Tnh cht vt l: Quy lut bin i nhit nng chy, nhit si ca cc cht trong dy ng ng benzen. Tnh cht ho hc: Phn ng th (quy tc th), phn ng cng vo vng benzen. Phn ng th v oxi ho mch nhnh.

HS hiu:
Cu to c bit ca vng benzen: cu trc phng v phn t c dng hnh lc gic u, c h lin kt lin hp l nguyn nhn dn n benzen th hin tnh cht ca hirocacbon no v khng no.
2. K nng

Vit c cng thc cu to ca benzen v mt s cht trong dy ng ng.

Vit c cc phng trnh ho hc biu din tnh cht ho hc ca benzen v mt s cht trong dy ng ng, vn dng quy tc th d on sn phm ca phn ng.

Tnh khi lng benzen, toluen tham gia phn ng hoc thnh phn phn trm v khi lng ca cht trong hn hp.
3. Tnh cm, thi

Hiu c cch gii quyt mu thun gia cu to v tnh cht ho hc ca hirocacbon thm to nn s hng th khi gii quyt vn mi.
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B. chun b ca GV v HS

GV:

My tnh, my chiu, cc phiu hc tp. Ho cht : Benzen, toluen, dung dch brom trong CCl4. Dng c: ng nghim, cp ng nghim, b gi th nghim.

HS: n tp kin thc bi ankaien v xem trc bi benzen v ng ng.

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I. cu trc, ng ng, ng phn v danh php Hot ng 1 1. Cu trc ca phn t benzen a) S hnh thnh lin kt trong phn t benzen

GV chiu m hnh biu din s hnh HS quan st v nhn xt. thnh lin kt v lin kt benzen ln mn hnh (hoc cho HS xem hnh 7.1 SGK):

Su nguyn t C trong phn t benzen trng thi lai ho sp2 . Mi nguyn t C s dng 3 obitan GV hng dn HS quan st v yu cu lai ho to lin kt vi hai nhn xt v: nguyn t C bn cnh n v mt Trng thi lai ho ca nguyn t C. nguyn t H. S hnh thnh lin kt . Su obitan p cn li xen ph bn nhau to thnh h lin hp tng i S hnh thnh lin kt . H lin kt ca benzen c c im bn. Benzen khc vi cc hirocacbon no khc vi cc hirocacbon hc. hc l c h lin kt lin hp khp kn. b) M hnh phn t

GV chiu m hnh phn t benzen ln HS quan st v nhn xt. mn hnh:

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cho HS quan st v yu cu HS nhn xt: V tr tng i ca cc nguyn t trong vng benzen. Gc ho tr CCC v CCH. Cu trc ca vng benzen.

C 6 nguyn t H v 6 nguyn t C u nm trn cng mt mt phng. Gc ha tr lin kt u bng 1200 Khung C l mt hnh lc gic u, cc nguyn t nm trn cc nh ca hnh lc gic. c) Biu din cu to ca benzen

GV yu cu HS trnh by cc cch biu HS tho lun v a ra cc cch biu din cng thc cu to ca phn t din: benzen. C 2 cch biu din benzen u c GV b sung: Khi biu din cng thc ca benzen khng phi ghi r cc nguyn t H, ch khi cn mi ghi r.
Hot ng 2 2. ng ng, ng phn v danh php GV chiu ln mn hnh mt s cht c HS tho lun a ra kt qu cng thc: C6H5, C7H8, C8H10 C6H6 theo khi nim ng ng. Yu cu HS lp cng thc phn t C6H6(CH2)k C6+kH6 + 2k chung ca benzen. t 6+k = n (k, n N)

n > 6 k = n 6 thay vo ta c Cng thc tng qut CnH2n6 n > 6. GV chiu bng 7.1 SGK ln mn hnh, HS quan st, tho lun v a ra nhn xt: yu cu HS rt ra cc nhn xt: Ankylbenzen c nhng kiu ng Ankylbenzen c cc ng phn v: phn no. + V tr tng i ca cc nhm ankyl Khi no th ankylbenzen c hin xung quanh vng benzen. tng ng phn? + Cu to mch C ca nhnh. Cch gi tn cc ankylbenzen.
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 Cch nh s mch cacbon.

Cch gi tn ankylbenzen:

+ Tn h thng ca cc ng ng benzen gi bng: Tn nhm ankyl + benzen. + Khi vng benzen hai hay nhiu nhm ankyl th ch r v tr cc nhm ankyl trong vng benzen. GV yu cu HS xc nh cch nh s Cch nh s cc nguyn t C trong vng benzen sao cho tng ch s trong ng trong hai trng hp sau: tn gi l nh nht. CH3 CH3 CH3 1 1 CH
6 5 4 1
3

2 3

2 3 4

6 5

5 4

2 3

CH3

CH3

CH3

3 4

6 5

CH3

Cch nh s ng

Cch nh s sai

GV hng dn HS cch gi tn thng HS quan st v nhn xt. thng mt s ankylbenzen n gin. + Nu vng benzen c 2 nhm ankyl v tr: CH3 CH3 1,2 gi l v tr ortho k hiu (o-). CH3 1,3 gi l v tr meta k hiu (m-). metylbenzen (toluen) 1,2-imetylbenzen (o-imetylbenzen) (o- xilen) CH3 1,4 gi l v tr para k hiu (p-). CH3 CH3 V d: CH3 metylbenzen 1,2-imetylbenzen (o-imetylbenzen )

CH3 CH3 1,3-imetylbenzen m-imetylbenzen (m- xilen)

CH3 1,4-imetylbenzen p-imetylbenzen (p- xilen)

Yu cu HS nhn xt cch gi tn thng thng ca cc ankylbenzen.

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II Tnh cht vt l Hot ng 3 a) Nhit nng chy, nhit si v khi lng ring. GV chiu bng 7.1 ln mn hnh HS HS quan st tho lun a ra kt qu: xem thng tin v tnh vt l v yu cu + Benzen v ng ng l cht lng. HS rt ra cc tnh cht sau: o tng dn, t o + ts nc gim dn, c s bt Trng thi. thng p-xilen, m-xilen, o-xilen. Nhit si. Nhit nng chy. b) Mu sc, tnh tan v mi GV: Cho HS quan st mt mu benzen HS quan st v nhn xt: trong ng nghim v lm th nghim ho tan benzen vo nc v xng lc k cho HS quan st cc tnh cht nh: Mu, mi, kh nng ho tan trong nc Benzen l cht lng khng mu c mi thm, khng tan trong nc, tan v dung mi hu c. tt trong dung mi hu c. Sau cho brom, iot, lu hunh cao su vo benzen v lc, yu cu HS quan st Benzen l dung mi tt ho tan nhiu cht khc. v nhn xt. III. Tnh cht ho hc Hot ng 4

GV: Yu cu HS phn tch c im HS tho lun v nhn xt: cu to nhn benzen, t suy ra tnh c im cu to nhn benzen c cht ho hc. mch vng v h lin kt lin hp khp kn, v vy nhn benzen kh bn.

Cc hirocacbon thm c hai trung tm phn ng l:

+ Vng benzen. + Mch nhnh.

Kh nng phn ng ca ankylbenzen l phn ng th, phn ng cng, phn ng oxi ho.

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1. Phn ng th a) Phn ng halogen ho GV lm th nghim: Cho benzen vo HS quan st: brom khan (trong dung mi CCl4), lc Khng thy c hin tng g. nh yu cu HS quan st hin tng. Chng t benzen khng c phn ng cng vi dung dch brom. GV nu vn : Ti sao benzen c nhiu lin kt i trong phn t m khng lm mt mu dung dch brom ging nh anken, ankin? GV iu khin hng dn HS gii HS tham gia gii quyt vn . quyt vn . Liu lin kt trong benzen c khc D on lin kt trong benzen bn hn trong anken. lin kt trong anken? Yu t no lm cho lin kt trong Benzen c cu trc vng v ba lin benzen bn hn lin kt trong anken. kt lin hp khp kn lm bn cho cc lin kt . HS: Benzen c lin kt bn nn GV hng dn HS kt lun vn . khng lm mt mu dung dch brom. Vy benzen c kh nng phn ng vi Br2 khng? Ta lm tip th nghim. GV: Cho tip mt t bt st vo ng Khi cho bt Fe vo thy mu ca nghim cha benzen v brom khan, un brom nht dn v thy kh thot ra do v lc nh. Yu cu HS nu hin tng c phn ng th. v vit phng trnh ho hc minh ho . Phng trnh ho hc: Br GV gii thiu: Toluen phn ng vi + Br2 bt Fe brom trong iu kin c bt Fe cng c + HBr hin tng ging benzen. Yu cu HS phn tch kh nng th ca HS tho lun. toluen. Toluen c kh nng th vo 3 v tr ortho, meta, para. CH3

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Vit phng trnh ho hc bit brom HS vit phng trnh ho hc. th ch yu vo v tr ortho (41%) v CH3 para (59%). CH3 + Br2
bt Fe

Br (41%)

o-bromtoluen

- HBr

CH3 (59%) Br

GV b sung: p-bromtoluen Toluen d th brom hn benzen. Nu khng dng bt st m chiu sng th brom th H nhnh. Yu cu HS vit phng trnh ho hc. HS vit phng trnh ho hc. CH3 CH2-Br Nhm C6H5CH2 gi l nhm benzyl, nh sng nhm C6H5 gi l nhm phenyl. Yu + Br2 + HBr cu HS gi tn sn phm th. benzylbromua b) Phn ng nitro ho GV lm th nghim: Cho benzen vo HS quan st v nu hin tng: ng nghim cha sn hn hp H2SO4 v HNO3 c lc mnh hn hp 5 10 pht, sau rt hn hp vo cc nc lnh dng a thu tinh khuy u. (hoc GV trnh by th nghim trong C lp cht lng mu vng nht lng SGK) xung l nitrobenzen sn phm Yu cu HS nu hin tng, gii thch? ca phn ng gia benzen v HNO3 NO +
H2SO4c HNO3(c)

+ H2O

nitrobenzen

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GV b sung: Toluen phn ng th vi HNO3 d HS vit phng trnh ho hc: hn benzen, phn ng u tin th vo v CH3 tr ortho (58%) v para (42%). NO2 CH3 (58%) + HNO3
H2SO4

o-nitrotoluen

- H2O

CH3 (42%)

Nitrobenzen phn ng th vi HNO3 NO2 kh khn hn benzen v phn ng u Phng trnh ho hc: p-nitrotoluen tin th vo v tr meta. NO2 GV yu cu HS vit phng trnh ho NO2 H2SO4c hc ca toluen, nitrobenzen vi HNO3 + H 2O + HNO3 (c) c trong H2SO4 c v un nng. NO2
m-initrobenzen
c) Quy tc th vng benzen

GV yu cu HS nhn xt v mi quan h gia cht tham gia (benzen, toluen, nitrobenzen) v sn phm th trong phn ng th vo vng benzen.

HS tho lun v nhn xt: Tu vo cu trc ca cc hp cht thm m phn ng xy ra d dng hay kh khn hn so vi benzen v sn phm u tin th vo v tr ortho-para hay meta.

GV dng s sau y m t quy lut th vng benzen. X X Y (I) + X + Y ( II ) HS nghin cu s di s hng GV hng dn HS rt ra quy tc th dn ca GV a ra quy tc: vng benzen. + Hng I xy ra khi X l OH, NH2, OCH3, CH3phn ng th d hn benzen v nh hng vo v tr -o, -p.
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X Y

+ Hng II xy ra khi X l NO2, COOH, SO3H, CH3 phn ng th kh khn hn benzen v nh hng vo v tr -m. d) C ch phn ng th vng benzen GV trnh by c ch th vng benzen H X + X+ + - H+ X HS quan st v nghe ging.

GV gii thch s trn: Tc nhn tn cng trc tip vo vng benzen khng phi l phn t halogen hay axit m l cc tiu phn mang in tch dng do tc dng vi cht xc tc. Phn ng xy ra qua hai giai on: + Giai on 1: X+ tn cng vo vng benzen to thnh phc km bn. + Giai on 2: Phc km bn tch H+. GV hng dn HS: Vit c ch th ca phn ng th HS vit c ch th vo vng benzen: C ch 1: HNO3 vo benzen. HONO2 + H+ U H2O+ NO2 H2O+ NO2 U H2O + NO2+ H NO2 - H+ + + NO2+ C ch 2: 2Fe + 3Br2 2FeBr3 FeBr3 + BrBr U Br+[FeBr4] ( Br+[FeBr4] U Br+ + [FeBr4]) H Br Br + H + + Br+ NO2

Vit c ch th ca phn ng th Br2 vo benzen.

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Hot ng 5 2. Phn ng cng GV yu cu HS: t cu to phn tch HS: Nhn thm c 3 lin kt to thnh vng lin kt lin hp khp kh nng cng ca nhn thm. kn nn bn cho h lin kt nhng cng c th cng c H2, Cl2 iu kin c xc tc, nhit thch hp.

GV b sung: Benzen v ankylbenzen HS nghe ging. khng lm mt mu dung dch brom nhng cng c vi H2 khi c Ni hoc Pt, phn ng to thnh xicloankan, khng ph thuc vo t l gia benzen v hiro; phn ng cng clo khi chiu sng. Yu cu HS vit phng trnh phn ng Phng trnh ho hc: v gi tn sn phm. GV b sung thng tin cho HS v sn phm cng Cl2: Hexacloran l cht bt mu trng, trc y c dng lm thuc tr su (6.6.6), do c tnh cao nhng hexacloran phn hy chm nn ngy nay khng c s dng. + 3H2

Ni, t0

xiclohexan Cl + 3Cl2
nh sng

Cl Cl Cl hexacloran

Cl Cl

Hot ng 6 3. Phn ng oxi ha a) Phn ng oxi ho khng hon ton

GV lm th nghim cho benzen v toluen cho vo 2 ng nghim cha dung dch KMnO4, lc u cho HS quan st, sau un nng c 2 ng nghim. Yu cu HS: Nu hin tng. Gii thch.
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HS quan st v nu hin tng. Ban u c 2 ng nghim u khng c hin tng g. Nhn xt: iu kin thng benzen, toluen u khng lm mt mu dung dch KMnO4 .

 Rt ra nhn xt. Vit phng trnh ho hc minh ho.

Khi un nng th ng nghim cha

toluen, mu ca KMnO4 b nht dn ng thi c kt ta nu xut hin. GV nhn mnh: Cc ankylbenzen khi Phng trnh ho hc ca phn ng: un nng vi dung dch KMnO4 th ch c nhm ankyl b oxi ha. CH3 COOK

+ 2KMnO4

t0

+ 2MnO2 + KOH + H2O

Yu cu HS vit phng trnh ha hc HS kt lun: Benzen khng tc dng v a ra kt lun. vi KMnO4 ngay c khi un nng. Cc ankylbenzen ch phn ng vi KMnO4 khi un nng.
b) Phn ng oxi ha hon ton

GV: Lm th nghim t chy benzen: HS quan st: Benzen chy cho ngn Cho mt t benzen ln s ri t . la mu xanh v ta nhiu nhit. So vi cc hirocacbon khc th Yu cu HS quan st: benzen chy cho nhiu khi en (mui Nu hin tng. than). So snh vi hin tng t chy ca n cc hirocacbon ( hc), gii thch. Do trong benzen t l H thp nn nC Vit phng trnh ha hc. phn ng chy din ra cha c hon ton.
t 2C6H6 + 15O2 12CO2 + 6H2O t 2nCO2 + 2CnH2n 6 + (3n3)O2 o o

(2n6)H2O GV: T nhng tnh cht hc v benzen v cc ng ng, GV hng dn HS nhn xt v kh nng phn ng ca chng. HS nhn xt v kt lun:
Benzen v cc ng ng tng i d tham gia phn ng th hn so vi phn ng cng v bn vi cc cht oxi ha. l tnh cht ha hc c trng chung ca hirocacbon thm (gi l tnh thm).

87

IV iu ch v ng dng Hot ng 7 1. iu ch

GV gii thiu cho HS c hai phng php ch yu dng iu ch benzen v ng ng: Cch 1

iu ch t ankan hoc xicloankan, HS vit phng trnh ho hc iu ch o xt,t yu cu HS vit phng trnh ho hc CH [CH ] CH C6H6 + 4H2 3 2 4 3 o minh ho. xt,t C6H5CH3 + 4H2 CH3[CH2]5CH3 Cch 2 o xt,t C6H5CH=CH3 C6H6+CH2=CH2 Chng ct nha than hoc du m (trong nha than c cha kh nhiu benzen, toluen, xilen,).
GV cho HS bit trong nha than cha nhiu benzen v cc ankylbenzen. Hy cho bit ngi ta li dng c im no tch, phng php tch, gii thch. HS tho lun: Ngi ta li dng nhit si ca benzen v ankylbenzen tng i thp so vi cc cht c trong nha than nn d bay hi. V vy ngi ta dng phng php chng ct tch.

2. ng dng

GV chiu ln mu hnh tranh nh hay HS quan st v a ra s tm tt. bng ph gii thiu cc ng dng ca Cht do (polistiren). hirocacbon thm, yu cu HS tm tt Cao su(cao su buna S). cc ng dng c bn.
Hirocacbonthm T si, dung mi. Phm nhum, dc phm. Thuc n (TNT). Polime, nha trao i ion.

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Hot ng 8 cng c bi v bi tp v nh 1. Cng c bi GV khc su mt s kin thc cho HS v:

Cu trc, phn loi v danh php ca ankylbenzen. Tnh cht ho hc. Phn ng th d hn phn ng cng. Quy tc th vo vng benzen. Phn ng oxi ho nhnh ankyl, phn ng cng xy ra kh khn hn cc hp cht khng no khc hc. Phng php iu ch benzen v ng ng t nha than v t sn phm ca du m. GV chiu cc bi tp sau ln mn hnh HS tho lun. 1. Mt hn hp X gm 2 aren A, B u c M< 120. T khi ca X i vi C2H6 l 3,067. Bit rng A, B c th c nhnh v nhnh ny no. Xc nh s ng phn c th c vo cng thc phn t ca A, B.
A. C6H6 (1 ng phn), C8H10 (2 ng phn) B. C6H6 (1 ng phn), C8H10 (4 ng phn). C. C6H6 (1 ng phn), C7H8 (1 ng phn). D. C7H8 (1 ng phn), C8H10 (2 ng phn).
p n D 2. Cho cc cht sau.

NO2

CH=CH2

CH3 (V)

C 2H 5

(I) (II) (III) (IV) Kh nng phn ng th trn vng benzen tng theo th t. A. (I) < (IV) < (III) < (V) < (II). B. (III) < (II) < (I) < (IV) < (V) C. (II) < (III) < (I) < (IV) < (V). D. (II) < (I) < (IV) < (V) < (III).

p n C
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3. Hp cht thm A c cng thc phn t l C8H10. Cho A tc dng vi dung dch KMnO4 to ra mt axit c cu to i xng. A c tn gi nh th no?

A. etylbenzen. C. m- metyltoluen.

B. o- metyltoluen. D. p- metyltoluen.

p n D. 4. Mt hirocacbon A c CTPT l C8H10. A c bao nhiu ng phn cha vng benzen?

A. 3

B. 5

C. 4

D.6

p n C. 5. Hirocacbon X th lng c phn trm khi lng H xp x 7,7%. X tc dng c vi dung dch brom. Cht no sau y l cng thc phn t ca cht X? a. axetilen. b. vinylaxetilen. c. benzen. d. toluen. p n C 2. Bi tp v nh 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 (SGK) D. Hng dn gii bi tp SGK 1. a) S ;

b) ; e) ;

c) S ; g) S.

d) ;

2. S d ngi ta biu din cng thc cu to ca benzen bng mt hnh lc gic u vi mt vng trn trong v:

6 nguyn t C v 6 nguyn t H trong phn t benzen u nm trn mt mt phng. Cc gc ho tr u bng 1200. Cc lin kt CC u c di bng nhau. 6 obitan p xen ph bn hnh thnh mt s h thng obitan dng chung cho c phn t.
3. Cht c th cha vng benzen.

a)

C8H6Cl2,

d) C10H12(NO2)2 ( bt bo ho benzen l 4).

Cht khng th cha vng benzen. b) C10H16 : C bt bo ho =3 < 4. c) C9H14BrCl: C bt bo ho =2 < 4.

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4. a) Xut pht t cng thc chung ca dy ng ng benzen:

CnH2n6 (n 6). Nn ng ng c cha 8C c cng thc phn t l: C8H10 ; ng ng c cha 9C c cng thc phn t l: C9H12 ; b) Vit ng phn: C8H10: CH3 CH3 CH3 CH3 C9H12: CH3 C2 H 5 C2 H 5 C 2H 5 CH3 CH3 CH3 CH3-CH-CH3 CH3 CH3 H 3C CH2-CH2-CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 C2 H 5

5.

a)

C 2H 5

C 2H 5 b) Cl c) H 3C

CH3 CH3

CH3 d) Cl e)

CH3 g) Cl

CH3

Cl

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6. a) Cho benzen vo ng nghim cha dung dch brom trong nc, lc k c hin tng benzen khng lm mt mu dung dch brom, cht lng phn lm hai lp: Lp cht lng trn l dung dch brom trong benzen c mu vng nht. Lp di l nc khng mu.

V benzen khng phn ng vi nc brom nhng ho tan brom tt hn nc. b) Cho brom lng vo ng nghim cha benzen, lc k yn th thnh dung dch ng nht v mu brom nht i do brom tan tt trong benzen. c) Cho thm bt st vo ng nghim th nghim B ri un nh: C kh thot ra, mu brom nht dn. Do cu to c bit ca benzen nn benzen ch tc dng vi brom khan khi c xc tc. Kh thot ra l kh HBr. 7. Phng trnh ho hc: CH3 Cl + HCl a) CH3 + Cl2
bt Fe

CH3 + HCl Cl

b)

CH3 + Cl2
nh sng

CH2Cl + HCl C2 H 5 NO2

c) C 2H 5 + HNO3
H2SO4 c

H 2O

C 2H 5 + NO2 H2O

CH3 d) + 3H2
Ni, t0

CH3

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8. Ly vo mi ng nghim nh s th t mt s t cc cht trn. Cho vo mi ng mt lng dung dch brom trong CCl4. Nu ng nghim no lm nht mu dung dch brom th ng nghim ban u l xiclohexen.

+ Br2

Br Br

Tip tc cho vo hai ng nghim cn li mt lng brom, thm cht bt Fe xc tc, un c hai ng nghim v a vo ming hai ng nghim mt mu giy qu m. Quan st thy ng nghim no giy qu ho th ng ban u l ng nghim ng benzen. Br
bt Fe

+ Br2

+ HBr

Cn li l ng ng xiclohehan. 9. V C8H10 khng lm mt mu dung dch brom C8H10 l hp cht thm, v nu l hp cht khng no th lm mt mu dung dch brom. Khi hiro ho mch C khng b bin i, v vy t cng thc cu to ca C8H10 ta vit c phng trnh ho hc nh sau: CH3 CH3 + 3H2
Ni, to

CH3

CH3

1,4-imetylbenzen
10. a) Tng t nh hnh 7.3 SGK.

b) Phng trnh ho hc:

bt Fe C6H6 + 3H2 C6H5Br 100.0,879 = 1,127 (mol) S mol C6H6 = 78

+ HBr

S mol brom cn dng l 1,127 (mol) 1,127.160 Vy th tch brom cn dng l = 58,168 (ml) 3,1 c) S mol HBr sinh ra l 1,127 (mol) S mol NaOH cn dng hp th ht HBr: 1,127 (mol). Khi lng NaOH: 45,08 (gam)
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d) Hn hp sau phn ng gm: C6H5Br; HBr ; C6H6(d) ; Br2(d). Ra hn hp bng dung dch kim : HBr + NaOH NaBr + H2O Br2 + 2NaOH NaBr + NaBrO + H2O Chit ly hn hp C6H5Br v C6H6. Chng ct, ui benzen v thu brombenzen nhit gn 1560C. e) Hiu sut phn ng: Khi lng brombenzen theo l thuyt: m = 1,127. 157 = 176,7 (g) 176,940 Th tch brombenzen: = 118,35 ml 1,495

Hiu sut phn ng;

80,00 . 100 = 67,60% 118,35

E. t liu tham kho

Phn ng th electrophin vo nhn thm l phn ng c trng ca benzen v cc dn xut ca benzen, k hiu l SEAr. C ch chung ca phn ng ny bt u bng s tn cng ca tc nhn electrophin vo h thng electron trong vng thm, khi to thnh phc khng thm, sau proton b th tch ra v to ra hp cht thm c mt ca nhm mi tn cng vo: H + E+ tn cng ca tc nhn electrophin (1) + E ti to hp cht thm E + H+

(2) ion benzoni (phc ) C ch ny gm 2 giai on, giai on (1) xy ra chm, cn giai on (2) din ra nhanh chng. Cc cu to gii hn phc trn c th c biu din bng cu trc cng hng sau y: H E +
94

+ H E +

H E +

H E

S 2 giai on m t trn l s c n gin ho. Thc t hp cht thm v tc nhn ca electrophin c th to phc yu trc lc to phc . Phc yu ny gi l phc . Trong phc , h thng electron tham gia nh l cht cho electron, cn tc nhn electrophin l cht nhn. S to thnh v phn li phc xy ra rt nhanh, khng nh hng n tc phn ng cng nh bn cht ca hp cht to thnh.

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Bi 47

stiren v naphtalen

A. Mc tiu bi hc 1. Kin thc

HS bit:

Cu to, tnh cht, ng dng ca stiren v naphtalen. Bit so snh cu to, tnh cht ca stiren, naphtalen vi cc ankylbenzen.
HS hiu:

Tnh cht ho hc ca stiren: trng hp, ng trng hp, phn ng oxi ho, cng vo nhnh hoc vng benzen.
Tnh cht ho hc ca naphtalen: Phn ng th brom v nitro ho, cng hiro, oxi ho bng oxi khng kh (c xc tc V2O5).

2. K nng

Vit c cng thc cu to , t d on tnh cht ho hc ca stiren v naphtalen.

Vit c cc phng trnh ho hc minh ho tnh cht ho hc stiren v naphtalen.

Phn bit mt s hirocacbon thm bng phng php ho hc. Gii bi tp: Tnh khi lng sn phm thu c sau phn ng trng hp v bi tp khc c ni dung lin quan.
B. chun b ca GV v HS

GV:

My tnh, my chiu, cc phiu hc tp. Ho cht: Naphtalen (bng phin), HNO3 c. Dng c: ng nghim, n cn, cc thu tinh 200ml, b gi

th nghim.

HS: n tp kin thc v benzen v ankylbenzen.

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C. tin trnh dy hc Hot ng ca GV Hot ng 1 Kim tra bi c Hot ng ca HS

GV chiu hai bi tp trc nghim ln mn hnh cho HS tho lun. 1. Tnh thm l tnh: HS 1. A. Tng i d tham gia phn ng th, tng i kh tham gia phn ng cng. B. D tham gia phn ng cng v th. C. C mi thm c trng. p n A D. Tng i kh tham gia phn ng th, tng i d tham gia phn ng cng. 2. Tn hp cht c cng thc cu to HS 2. sau y l: NO
2

NO2 CH3 A. 4-mety-1,3-initrobenzen. B. 4,6-initrotoluen. C. 2,4-initrotoluen. D. 2,4-initrobenzen. p n C.

I. Stiren Hot ng 2 1. Cu to Cch 1 GV yu cu HS nghin cu SGK v HS nghin cu SGK v a ra nhn xt. nhn xt v : Cng thc phn t C8H8. CH=CH2 Cng thc phn t v cng thc cu Cng thc cu to: to ca stiren.
97

 V tr ca cc nguyn t trong phn Tt c cc nguyn t trong phn t t stiren. stiren u nm trn mt mt phng. c im cu to ca phn t stiren. c im cu to: + C vng benzen. + C mt lin kt i nhm th. GV yu cu HS d on tnh cht ho HS tho lun v nhn xt: hc ca stiren. + C tnh cht ca benzen. + C tnh cht ging anken. Cch 2 GV gii thiu cho HS bit: bng HS tho lun di s hng dn ca phng php phn tch nguyn t v GV a ra kt qu: xc nh khi lng mol phn t, ngi ta thit lp c cng thc phn t ca stiren l C8H8. un nng stiren vi KMnO4 ri axit GV hng dn v yu cu HS trnh ho thu c axit benzoic(C6H5COOH), by phng php chng minh cng chng t stiren c vng benzen v thc cu to ca stiren l c mt vng nhm th C6H5R, v cng thc phn t benzen v mt gc vinyl. l C8H8 nn R l C2H3. Cho stiren vo dung dch brom thy dung dch brom nht mu v to ra hp cht c cng thc C8H8Br2, iu chng t nhm C2H3 c lin kt i. GV b sung tnh cht vt l ca stiren stiren l cht lng, khng mu, nh hn nc v khng tan trong nc, tan nhiu trong dung mi hu c, c t s0 =146oC.
Hot ng 3 2. Tnh cht ha hc a) Phn ng cng

GV tng t anken yu cu HS vit HS vit phng trnh phn ng. cc phn ng ca stiren vi dung dch Phn ng vi dung dch brom: Br2, vi HBr, vi H2, vi dung dch KMnO4, phn ng trng hp.

98

CH=CH2+ Br2

CHCH2 Br Br

Phn ng vi HBr:
CH=CH2+ HBr CHCH3 Br CH2CH3
Ni, t ,p
0

Phn ng vi hiro:
CH=CH2 + H2
CH2CH3

CH2CH3
Ni, t0,p

+ 3H2
b) Phn ng trng hp

GV tng t anken th stiren c phn HS vit phng trnh ho hc. ng trng hp to ra polistiren. Yu Phn ng trng hp: cu HS vit phng trnh ho hc. CH=CH2 CHCH2 GV b sung: stiren d trng hp hn Xt, t0, p etilen nhiu ln. n n GV gii thiu stiren cn c phn ng polistiren ng trng hp vi buta-1,3-ien nh sau: nCH2=CHCH=CH2 + nC6H5CH=CH2
xt,t ,p (CH2CH=CHCH2CHCH2)n o

HS tho lun: GV yu cu HS nu khi nim phn Phn ng ng trng hp l phn ng ng ng trng hp. trng hp ng thi hai hay nhiu loi monome khc nhau. c) Phn ng oxi ho GV gii thiu: Stiren phn ng c HS nghe ging. vi dung dch thuc tm nhit thng, phn ng ch oxi ho gc
99

C6H5 Cao su bunaS

vinyl cn vng benzen vn gi nguyn. GV hng dn HS vit s phn ng. GV: Stiren cng tham gia phn ng th nguyn t hiro vng benzen.
Hot ng 4 3. ng dng

GV: Chiu ln mn hnh tranh nh hay bng ph gii thiu cc ng dng ca hirocacbon thm, yu cu HS tm tt cc ng dng c bn

HS tho lun, tng hp:

ng dng quan trng nht l sn xut polime (polistiren). sn xut t si, cao su. Dung mi.

II. naphtalen Hot ng 5 1. Tnh cht vt l v cu to GV: Cho HS quan st mu naphtalen HS quan st v nhn xt v tnh cht vt (bng phin), sau lm th nghim l ca naphtalen: s thng hoa, ho tan naphtalen trong nc v dung mi hu c. Yu cu HS nhn xt v: Trng thi. Cht rn. Mu sc. Mu trng. Mi. C mi hc c trng. Kh nng ho tan, thng hoa. Khng tan trong nc, tan tt trong benzen. Nu khng c iu kin lm th Naphtalen thng hoa nhit thng. nghim th GV b sung: Naphtalen c tnh thng hoa nhit thng, nhit nng chy 800C, tan tt trong HS: Ghi bi. benzen, ete

GV chiu cng thc cu to naphtalen

100

ln mn hnh:
7 6

1 2 3

HS quan st v nhn xt:

yu cu HS nhn xt v: Cu to phn t. V tr cc nguyn t trong phn t Naphtalen cu to bi 2 vng benzen. naphtalen. Cc nguyn t trong naphtalen nm trn mt mt phng.
Hot ng 6 2. Tnh cht ha hc

GV: T cu to yu cu HS d on HS: Naphtalen c cu to bi 2 vng tnh cht ha hc ca naphtalen. benzen nn c tnh cht ha hc ging benzen: C phn ng th.

Phn ng cng H2. Khng lm mt mu dung dch KMnO4 iu kin thng. a) Phn ng th
GV gii thiu: Naphtalen c phn ng HS vit phng trnh ho hc ca phn th tng t benzen v u tin th vo ng: v tr s 1. Yu cu HS vit phng trnh ca naphtalen vi Br2 v HNO3. Br + Br2
bt Fe

+ HBr NO2

HNO3, H2SO4 c - H2O

b) Phn ng cng

GV tng t benzen yu cu HS vit HS vit phng trnh ho hc: phng ho hc ca naphtalen vi H2. Ni, t0, p + 2H 2 GV gi v b sung tn sn phm cc giai on cho HS. tetralin
101

Ni, t0, p

+ 3 H2 ecalin
c) Phn ng oxi ho

GV gii thiu: Tng t benzen, naphtalen HS nghe ging. khng b oxi ho bi dung dch KMnO4. Khi c mt xc tc V2O5 nhit cao th naphtalen b oxi ho O2 (kk) theo s : 0
V2 O 5 . t

O C O C O anhirit phtalic

Hot ng 7 3. ng dng

GV yu cu HS nu mt s ng dng HS tho lun, nu cc ng dng: ca naphtalen, sau GV b sung. Lm nguyn liu tng hp ho hc. Lm nguyn liu trong cng nghip cht do. Naphtalen cn c dng lm cht chng gin, cc sn phm hiro ho cn c dng lm dung mi
Hot ng 8 Cng c bi v bi tp v nh 1. Cng c bi GV nhc li cc kin thc cn nm vng trong bi hc:

Cu to: Stiren gm mt vng thm v mt gc vinyl, naphtalen cu to gm hai vng benzen. Tnh cht vt l, tnh cht ho hc: c tnh thm (tng t benzen) v mt s tnh cht ring ca stiren v naphtalen. Phng php iu ch v ng dng ca stiren, naphtalen. GV chiu cc bi tp sau ln mn hnh cho HS tho lun.
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1. Kt lun no sau y khng ng?

A. Stiren khng lm mt mu dung dch brom. B. Stiren cn c tn gi khc l vinylbenzen, C. Cc nguyn t trong phn t benzen cng nm trn mt mt phng. D. Stiren va c tnh cht ging benzen va c tnh cht ging anken.
p n A. 2. Hirocacbon A c cng thc dng (CH)n. Mt mol A phn ng va vi 4 mol H2 (Ni, to) hoc 1 mol Br2 (trong dung dch). Tn ca A l: A. Axetilen B. Vinylaxetilen C. Benzen D. Stiren p n D 3. Cho s sau:

CnH2n6 (X) (A) Cao su bunaS.

Bit X l hp cht thm. Cng thc phn t ph hp ca X l: B. C6H5CH2CH2CH3. A. C6H5CH3. C. C6H5C2H5 D. C A v B.

p n C. 2. Bi tp v nh 1, 2, 3, 4, 5, 6 SGK D. hng dn gii bi tp SGK 1. Ba cng thc sau:

u l cng thc cu to ca naphtalen.

2. Vit cng thc cu to ca cc cht:

a)

o-clostiren

m-nitrostiren CH=CH2 NO2

p-flostiren CH=CH2 F

CH=CH2 Cl

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b) -clonaphtalen Cl

-metylnaphtalen
CH3

2-nitronaphtalen NO2

1-flonaphtalen

3. Stiren (C8H8) phn ng vi brom c mt bt Fe thu c ba cht c cng thc C8H7Br3 (mt nguyn t Br tham gia phn ng th, hai nguyn t Br tham gia phn ng cng). Cc phng trnh ho hc:

CH=CH2+ Br2

CHCH2 Br Br CHBrCH2Br Br + HBr

CHBrCH2Br + Br2
bt Fe t0

CHBrCH2Br + HBr

Br CHBrCH2Br
4. S phn ng ho hc:

Br O

HBr

O2 (kk) V2 O 5 . t0

C C O

H2O

COOH COOH

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5. a) Dng dung dch KMnO4:

Stiren lm mt mu dung dch KMnO4 nhit thng tng t etilen: 3C6H5CH=CH2 + 2KMnO4+4H2O3C6H5CHCH2 + 2MnO2 +2KOH
OH OH Etylbenzen lm mt mu dung dch KMnO4 khi un nng:
t 3C6H5CH2CH3 + 12KMnO4 3C6H5COOK +12MnO2 +6KOH + 3K2CO3 +3H2O o

Benzen khng lm mt mu dung dch KMnO4 ngay c khi un nng n 40oC.

b) Dng dung dch AgNO3 trong NH3: Phenylaxetilen cho kt ta: C6H5CCH + AgNO3 + NH3 C6H5CCAg + NH4NO3

Stiren khng c phn ng trn. 6. a) Phng trnh ho hc iu ch stiren:

+ CH2=CH2 CH2CH3
ZnO, t
o

H+

CH2CH3 (1)

CH=CH2 + H2 (2)

Theo phn ng (1) ta c:

10 6 (mol) 78 Kt hp (1) v (2) ta c :
n C 2 H4 = n C 6 H6 =

VC2 H4 =

10 6 .22,4 = 0,29.106 = 290 (m3) 78 1 mol C8H8 1 mol C6H6

78 kg 10 kg
3

104 kg x kg

Khi lng C8H8 theo l thuyt l:

10 .104 (kg). 78 Nhng hiu sut = 80% mi giai on nn:

x=

x=

10 3.104 .0,8.0,8 = 853 (kg). 78

105

Bi 48

ngun hirocacbon thin nhin

A. Mc tiu bi hc 1. Kin thc

HS bit:

Thnh phn ho hc, tnh cht, cch chng ct v ch bin du m bng phng php ho hc. ng dng cc sn phm t du m. Thnh phn ho hc, tnh cht, cch ch bin v ng dng ca kh m du v kh thin nhin. Thnh phn, cch ch bin, ng dng ca than m.
HS hiu:

V sao du m c mi kh chu? Ti sao du m khng c nhit si nht nh? Ti sao kh thin nhin v kh m du c dng lm nhin liu cho cc nh my nhit in? Tm quan trng ca lc ho du vi nn kinh t.
HS vn dng:

Bit phn bit thnh phn ca kh thin nhin, kh m du, kh l cc; Gii thch ngha qu trnh ch bin ho hc cc sn phm chng ct phn on du m (crackinh v rifominh).
2. K nng

c, tm tt c thng tin trong bi hc, tr li cu hi, rt ra nhn xt. Tm c thng tin, t liu v du m v than Vit Nam. Tm hiu c ng dng ca cc sn phm du m, kh thin nhin, than m trong i sng.
3. Tnh cm, thi

T nhng hiu bit v du m, kh thin nhin, than m, lm cho HS bit qu trng v s dng tit kim ngun hirocacbon (nhin liu ho thch).

106

B. chun b ca GV v HS

GV:

My tnh, my chiu, cc phiu hc tp. Bng biu, phn mm m phng. Mu du m v mt s sn phm t du m.

HS: n tp kin thc v cc hirocacbon hc.

C. tin trnh dy hc Hot ng ca GV A. Du m I. trng thi t nhin, tnh cht vt l v thnh phn ca du m Hot ng 1 1. Trng thi t nhin v tnh cht vt l Hot ng ca HS

GV cho HS quan st mu du m, sau HS quan st v a ra nhn xt: lm th nghim ho tan du m trong nc (hoc GV chiu mt on video clip v du m ln mn hnh cho HS quan st). Yu cu HS nhn xt v:

Trng thi iu kin thng. Mu sc, mi. Khi lng ring so vi nc. Tnh tan trong nc ca du m.

Du m l cht lng snh. Mu nu en, c mi c trng. Nh hn nc. Khng tan trong nc.

Du m thng c khai thc t m Du m thng c khai thc du trong lng t (trong lc a cng u? nh ngoi thm lc a).
GV lin h vi s c trn du trn bin nc ta gy nguy hi cho mi trng.

107

Hot ng 2 2. Thnh phn ho hc

GV yu cu HS nghin cu SGK v HS nghin cu SGK v nhn xt: nhn xt : Thnh phn ca du m l hn hp ca Thnh phn ca du m. rt nhiu hirocacbon c chia lm cc nhm: + Nhm ankan t C1 n C50. + Nhm xicloankan gm ch yu l xiclopentan v xiclohexan. + Nhm hirocacbon thm gm benzen, toluen, xilen, naphtalen v cc ng ng. + Ngoi thnh phn chnh, du m cn c mt lng nh hp cht hu c cha nit, oxi, lu hunh v cc hp cht v c khc. Du m c mi kh chu gy hi cho Ti sao du m li c mi kh chu cc ng c l do cc hp cht cha lu hunh trong du m. gy hi cho ng c? Du m Vit Nam c hm lng S thp (< 0,5%) nn thun li cho vic Ti sao du m Vit Nam li thun ch bin v s dng. tin cho vic ch ha v s dng?
II chng ct du m Hot ng 3 1. Chng ct p sut thng a) Chng ct phn on trong phng th nghim

GV yu cu HS nu c s ca phng HS nu c s ca phng php chng php chng ct du m. ct, da vo nhit si khc nhau ca cc cht c trong du m. GV chiu hnh 7.4 SGK ln mn hnh. HS quan st v tr li. Hn hp c nhit si thp thu c nhit thp, nhit cng cao th thu c hn hp cc cht c nhit
108

si cng cao hp cht c nhit si cao b ngng ng dn t di ln.

Yu cu cho HS quan st v nhn xt v sn phm theo nhit . b) Chng ct phn on du m GV: Chiu mt on video clip v hot ng chng ct du m ln mn hnh. Yu cu HS: Nu tc dng ca vic s ch du m. HS quan st v nhn xt:

Du m sau khi c khai thc (du th) c s ch loi b nc v mui trc khi em chng ct. L thp cao khong vi chc mt, qu trnh chng ct l lin tc.

Nu cu to ca thp chng ct v qu trnh chng ct.

GV chiu bng 8.2 SGK ln mn hnh:
t s ( C) S nguyn t C trong phn t < 180 170 270 250 350 350 400 > 400
0 0

HS quan st v nhn xt.

Hng x l tip theo

110 phn on Chng ct p sut cao kh v xng 1016 phn Tch S nhin liu on du ho lm

1621 phn Tch S lm on du iezen nhin liu 2130 phn Sn xut du on du nhn nhn >30 cn mazut Chng ct p sut thp

Yu cu HS nhn xt mi quan h s Tch c cc phn on du m khc nhau. nguyn t C vi nhit si. Khi nhit tng th thu c cc phn on c s C tng dn.
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Hot ng 4 2. Chng ct di p sut cao

Phn on dng chng ct p sut cao l phn on xng v kh c t0s < 1800C. tch cc phn on nh hn phn Cc sn phm thu c, ng dng on xng kh. + Phn on C1C3, C3C4 c dng lin quan n sn phm. lm nhin liu kh hoc kh ho lng GV hng dn HS rt ra nhn xt. hoc lm nguyn liu sn xut ho cht khc. + Phn on C5C6 gi l ete du ho c lm dung mi hoc nguyn liu cho nh my ho cht. + Phn on C6C10 gi l xng nhng thng l xng c cht lng thp.
Hot ng 5 3. Chng ct di p sut thp GV yu cu HS tm hiu SGK v rt ra HS tho lun v a ra kt qu: sn phm ca qu trnh chng ct p Phn on linh ng sut thp. Du nhn

GV cho HS nghin cu SGK v yu cu nhn xt v: Phn on dng chng ct di p sut cao. Mc ch ca chng ct p sut cao.

HS nghin cu SGK v nhn xt:

Vazlin Parafin Atphan GV hng dn HS lin h cc sn Du nhn dng bi trn, lm mt, phm v ng dng ca chng. lm sch ng c Vazlin v parafin dng trong y hc v lm nn. Atphan (cn en) dng ri ng.

Cn mazut

Phn on linh ng dng crakinh.

110

III. Ch bin du m bng phng php ho hc Hot ng 6

GV nu mc ch ca vic ch ho du HS nghe ging v ghi bi m. p ng nhu cu v s lng v cht lng xng lm nhin liu. + Cht lng xng c o bng ch s octan, ch s octan c quy c nh sau: 2,2,4trimetylpentan c kh nng chng kch n rt tt c coi l ch s octan l 100. + Ch s octan gim theo trt t sau: aren > anken c nhnh > ankan c nhnh > xicloankan c nhnh > anken khng nhnh > xicloankan khng nhnh > ankan khng nhnh. p ng nhu cu v nguyn liu cho cng nghip ho cht: Cng nghip ho cht cn rt nhiu anken, aren tng hp ra polime v cc ho phm khc m trong thnh phn du m c rt t hoc khng c. GV yu cu gii thch cc vn sau: Ti sao phi ch bin ha hc cc phn on du m? Phng php no thng dng trong ch bin ha hc?

HS nghin cu SGK v nhn xt: Ch bin ha hc tng gi tr s dng ca du m. Phng php thng dng l crackinh v rifominh.

1. Rifominh GV b sung: Rifominh l qu trnh HS tho lun v a ra kt qu: dng xc tc v nhit lm bin i cu trc phn t t mch cacbon khng + Chuyn ankan mch thng thnh nhnh thnh mch phn nhnh (ng ankan mch nhnh v xicloankan. phn ha) hoc t khng thm thnh
111

thm. Yu cu HS ly v d minh ha.

CH3[CH2]3CH3

xt, t0

CH3CHCH2CH3 CH3 + H2

CH3[CH2]4CH3

xt, t0

+ Tch H2 chuyn xicloankan thnh aren:

xt, t0

+ 3H2

+ Tch H2 chuyn ankan thnh aren: GV dng bng ph nh sau tm tt 0 qu trnh rifominh, yu cu HS tm tt CH [CH ] CH xt, t 3 2 5 3 sn phm ca qu trnh rifominh. Ankan c C6-C7, C7-C8, C8 HS tho lun v a ra kt qu Ankan c C6-C7, C7-C8, C8
Rifominh 5000C, 20-40atm, Pt, Pd, Ni /Al2O3

CH3 + 4H2

Rifominh 5000C, 20-40atm, Pt, Pd, Ni /Al2O3

Xng: C5-C11 C ch s octan cao hn 2. Crackinh

GV gii thiu cho HS: Crackinh l qu trnh b gy phn t hirocacbon mch di to thnh cc phn t, hirocacbon mch ngn hn nh tc dng ca nhit hoc ca xc tc v nhit.

Benzen (C6H6), toluen (C7H8)

Xilen (C8H10) stiren (C8H8)

Yu cu HS nhn xt: Phn on no ca du m thng HS nhn xt: Phn on thng dng crackinh dng crackinh?
112

l cc phn on nng nh du nhn, Sn phm ca qu trnh crackinh l du iezen Sn phm ch yu l xng v kh g? crackinh (gm ch yu l metan, etan, etilen, butilen,) a) Crackinh nhit GV gii thiu: Phng php crackinh HS vit phng trnh ho hc. nhit l phng php dng nhit C3H8 + C2H4 b gy mch C, yu cu HS vit C2H6 + C3H6 Crackinh phng trnh ho hc crackinh C5H12. C5H12 CH4 + C4H8 GV yu cu HS nu ng dng ca C5H10 + H2 HS nu ng dng. crackinh nhit. Ch yu l to ra anken dng lm monome sn xut polime. b) Crackinh xc tc GV yu cu HS xem thng tin trong SGK v nhn xt: Phn on no l phn on ch yu dng crackinh xc tc. Mc ch chnh ca crackinh xc tc. GV chiu hnh 7.6 SGK ln mn hnh. Yu cu HS tm tt qu trnh ch bin v ng dng ca cc sn phm lin quan. GV hng dn HS kt lun cc giai on ch bin du m. HS nghin cu SGK.

Phn on c nhit si cao C21 C35. Ch yu chuyn hirocacbon mch di thnh thnh xng nhin liu. HS quan st v nhn xt. HS kt lun: Ch bin du m bao gm chng ct du m v ch bin bng phng php ho hc(crackinh v rifominh).

B. Kh m du v kh thin nhin Hot ng 7 I. Thnh phn kh m du v kh thin nhin

GV chiu bng sau ln mn hnh:

113

Cc hp phn

Khong % th tch Kh m Kh thin du nhin

Metan Etan Propan Butan Pentan (kh) Cc kh khc

50 70 20 11 4 2 12

70 95 28 2 1 1 4 20

HS xem thng tin v nhn xt: Yu cu HS xem thng tin v nhn xt Kh thin nhin c thnh phn ch v thnh phn ca kh thin nhin v yu l CH4 (95%) v mt s ng ng kh m du. thp ca CH4 nh C2H6, C3H8.

Kh m du thnh phn gm c CH4 (5070%) th tch v mt s ankan khc.

Hot ng 8 II. Ch bin, ng dng ca kh m du v kh thin nhin

GV chiu s ch bin v ng dng HS quan st phn tch s v nhn ca kh thin nhin, kh m du ln xt: mn hnh cho HS quan st:

Kh thin nhin hoc kh m du

Nh my kh Loi b H2S, nn v lm lnh

ng dng 1

ng dng 2

114

Yu cu HS nhn xt: Ti sao phi loi b H2S. Nu cc ng dng ca kh thin nhin v kh m du. GV b sung: Kh thin nhin v du m Vit Nam c cht lng tt do cha rt t hp cht ca lu hunh.

Kh H2S l kh c hi (n mn) cho cc thit b s dng kh thin nhin v kh m du. Dng lm nhin liu cho nh my nhit in. L ngun nhin liu, nguyn liu quan trng.

C. than m Hot ng 9

GV yu cu HS nghin cu SGK v tr li h thng cc cu hi sau: Nguyn nhn hnh thnh than m l g? C nhng loi than m no?

HS nghin cu SGK, tho lun v tr li. Than m l phn cn li ca cy c c i b bin ha. C 3 loi chnh: + Than gy. + Than m. + Than nu.

I. Chng kh than bo

GV cho HS nghin cu s trong SGK Yu cu HS nhn xt v: Nguyn liu iu ch than cc, iu kin iu ch. Sn phm thu c t qu trnh ny.

HS nghin cu SGK v nhn xt: thu c than cc cn i t than m, iu kin nhit khong 10000C. Phn kh: + Kh l cc gm 65% H2, 35% CH4, CO, CO2, C2H6, N2 + Lp nc + NH3. + Lp nha gi l nha than . Phn rn: Than cc. Kh l cc l hn hp cc cht d chy.

c im ca kh l cc.

ng dng ca cc sn phm thu ng dng cc sn phm thu c: c. + Kh l cc dng lm nhin liu.

115

+ Lp nc v NH3 dng lm phn m. + Lp nha c x l tip. + Than cc dng cho luyn kim.
II. Chng ct nha than

GV nu ra cc vn cho HS tho HS tho lun v tr li . lun. Nha than l cht lng c cha Nha than l g? nhiu hirocacbon thm v phenol. T nha than , tch c:

T nha than ngi ta tch c nhng phn on no. Thnh phn ca mi phn on? GV hng dn HS tho lun.

+ Phn on si 801700C gi l du nh gm: benzen, toluen, xilen, + Phn on si 1702300C gi l du trung gm: phenol, naphtalen, piriin + Phn on si 2302700C gi l du nng gm: Crezol, xilenol, quinolin. + Phn cn cn li l hc n ri ng.

Hot ng 10 Cng c bi v bi tp v nh 1. Cng c bi

GV chia lp thnh cc nhm tho lun HS tho lun cng c bi hc. gip HS khi qut ha li kin thc trong bi. C nhng ngun hirocacbon no trong t nhin? Thnh phn, cch khai thc, ch bin du m.

Nu ng dng ca cc ngun hirocacbon .

116

2. Bi tp v nh 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11(SGK) D. Hng dn gii bi tp SGK 2. p n C. 4. i vi phn on si < 1800C, cn phi chng ct di p sut cao, v phn on ny s nguyn t C t 1 4 l ch yu v tn ti ch yu di dng kh d bay hi nn phi dng di p sut cao mi tch c C1 C2 , C3 C4. i vi phn on si > 3500C , cn phi chng ct di p sut thp, v thnh phn ch yu phn on ny l cn mazut c nhit si cao. 6. Crackinh nhit Crackinh xc tc

Mc ch ch To anken, lm monome Chuyn hp cht mch di c ts yu sn xut polime cao thnh xng nhit liu iu kin tin Nhit cao hnh Sn phm ch Anken yu Sn phm khc C xc tc, nhit thp hn Xng c ch s octan cao

Ankan, dng lm nhin Kh, du liu cho crackinh 7. Nhn nh ng: d)

8. Mc ch Nguyn liu ( Phn on, ts) Du m, phn on xng, ts 50 2000C Du m, phn on xng, ts 50 2000C Du m, phn on du iezen ts250 3500C Du m, phn on kh v xng, ts < 1800C Than , phn on si, ts < 170C Phng php Crackinh xc tc

Xng cho mt, taxi Nhin liu cho my bay, phn lc Nhin liu cho ng c iezen Etilen, propilen Hn hp benzen, toluen, xilen

Crackinh xc tc

Chng ct Chng ct di dng p cao tch phn on Chng ct than

117

9. a) Thnh phn (% V)

Kh du m

Kh thin nhin

ng dng

CH4 C2H 6 C3H 8 C4H10 C5H12 N2, H2, H2S, He,

51 19 11 4,4 2,1 12,5

92 1,9 0,6 0,3 1,1 4,1

Nh my in, s, m, sn xut ancol. iu ch PE. Kh ho lng (gas) lm nhin liu cho cng nghip, i sng. Nguyn liu cho crackinh.

Kh l cc : H2 (65%) , CH4 (25%), CO2, CO, N2, H2, .lm nhin liu. Kh crackinh l hn hp kh gm ch yu hirocacbon nh CH4, C2H2, C3H6... ph thuc vo iu kin phn ng. Dng lm nguyn liu cho tng hp hu c.
b) Nha than l phn lng thu c khi chng ct than . Lp nha khng tan trong nc t tch ra. mi phn on thu c hp cht: Du nh: (801700C) cha benzen, toluen, xilen Du trung: ( 170 2300C ) cha naphtalen, phenol, piriin, Du nng: ( 230 2700C) cha crezol, xilenol, 10. Vi 1g hn hp gm: C6H14 : 0,43 g ; C7H16 : 0,495 g ; C5H12 : 0,018 g ; C8H18 : 0,057 g Khi t chy hn hp, ta thu c : 0,018 0,057 0,43 0,495 + 7. + 5. + 8. ).22,4 = 1,56576 (1) VCO 2 = ( 6. 86 100 72 114 Phng trnh ho hc ca phn ng t chy: 3n + 1 O2 nCO2 + (n +1) H2O CnH2n+2+ 2 Suy ra: VO 2 = (
19 25 .5.10 3 + 11.4,95.10 3 + 8.2,5.10 4 + 5.10 4 ) . 22,4 2. 2 = 2,468(1) nn VKK = 2,4684 x 5 = 12,34 (1).

118

11. a) Theo bng: propan u c khi lng ring v nhit si u nh hn so vi butan, v th gas no cha nhiu propan s c khi lng ring nh hn nhng li c p sut hi ln hn.

b) Tnh nhit lng to ra khi t gas:

1000g
propagas

etan: 1,7%

17 g 968 g 15 g

propan: 96,8% butan: 1,5%

pentan: 0% 17 968 15 .2219 + .2877 = 50446,05(kJ) H = .1560 + 30 44 58

1000g
butagas

etan: 0% propan: 4 g butan: 994g pentan: 2g

H =

4 994 2 .2219 + .2877 + .3536 = 49605,78 (kJ) 44 58 72 propan: 515 g

1000g
propa butagas

butan: 475 g

H =

pentan: 1 g 1 515 475 .2219 + .2877 + .3536 = 49583,14 (kJ) 44 58 72

Nhn xt: Tuy thnh phn khc nhau, nhng nhit lng thu c t mt n v khi lng khc nhau khng ng k.
c) V axetilen d sn xut t ngun nguyn liu vi v than c sn trong t nhin.
e. t liu tham kho Bt la gas: T chic bt la dng du ho, sau thay du ho bng xng lm cho vic s dng bt la tin li hn. Ti nay, chic bt la gas ang c s
119

dng ph bin, v dng n nhy hn, ngn la cao hn, khng khi, mu xanh v t mi. Gas (kh) dng trong bt la chnh l butan ho lng. Ta bit butan c nhit si 0,50C cn isobutan nhit 110C. nu nn butan trong bnh lm p sut tng ln (~ 810atm) th n ho lng vo bt la c np kn gn bnh xe mi la. Khi bt la cng l lc m np bt la cho kh bay ra, bt la v chy. Butan bt la nhy v chy nng, chy ht nn cho ngn la xanh v t mi. Hin nay trn th trng Vit Nam nhiu ngun gas c sn xut bt la gas nh Tin Hi (Thi Bnh), Th c (Du kh Si Gn) v mt s ngun khc na. D l ngun no i na, ngoi kh nng chy, ngi ta cng xem xt k kh thi ra khi chy, v sc kho ca ngi tiu dng.

120

Bi 49

luyn tp so snh c im cu trc v tnh cht ca hirocacbon thm vi hirocacbon no v khng no

A. Mc tiu bi hc 1. Kin thc

Cng c, h thng ho tnh cht ho hc v phng php iu ch hirocacbon. HS bit:

Nhng tnh cht vt l, tnh cht ho hc, nhng ng dng v phng php iu ch hirocacbon no, khng no v thm. S ging nhau, khc nhau v v tnh cht ho hc gia ankan, anken, ankin v benzen.
HS hiu:

Mi lin quan gia cu trc v tnh cht c trng ca hirocacbon thm, hirocacbon no v hirocacbon khng no. Phng php nhn bit gia cc loi hirocacbon.
2. K nng

Rn luyn k nng so snh, tm mi lin h gia kin thc c bn t c cch nh h thng. Vn dng kin thc hc t bit cch gii ng bi tp. Bit lp k hoch gii mt bi ton ho hc.
3. Tnh cm, thi thc cn thn, trung thc, kin tr, chnh xc trong hc tp ho hc. B. chun b ca GV v HS.

GV: My tnh, my chiu, h thng cc cu hi v bi tp n tp.

121

 HS:

n tp cc bi hirocacbon hc. Chun b trc ni dung luyn tp nh.

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I Kin thc cn nm vng Hot ng 1

GV nu cc vn c bn hc: Khi nim anken, ankaien, ankin. c im cu trc lin kt ca anken, ankaien, ankin, hirocacbon thm. Tnh cht ho hc c bn ca hirocacbon no, khng no v thm. Phng php iu ch v ng dng ca anken, ankaien, ankin, hirocacbon thm. GV chia HS theo cc nhm (4 nhm) v giao ni dung luyn tp cho cc nhm. GV yu cu HS (nhm 1) nu c im cu trc v kh nng phn ng ca hirocacbon thm, hirocacbon no v hirocacbon khng no. HS (nhm 1) chun b, tho lun v a ra kt qu: Hirocacbon thm.

C vng benzen vng benzen, 6 nguyn t C trng thi lai ho sp2 lin kt thnh mt hnh lc gic u, 6 electron p to thnh h lin hp chung, do bn hn cc lin kt ring r. V th aren tng i d th, kh cng, bn vi nhng cht oxi ho. Hirocacbon no. Ch c cc nguyn t C lai ho sp3 to thnh lin kt bn vng. V th tng i tr iu kin thng.

122

 Trong phn t khng c trung tm phn ng c bit no, v th phn ng thng to ra hn hp nhiu sn phm. Hirocacbon khng no. C C lai ho sp2 to thnh lin kt i hoc C lai ho sp to thnh lin kt ba. Trung tm phn ng ca phn t chnh l nhng lin kt km bn vng. Phn ng cng l phn ng c trng.
GV yu cu HS (nhm 2) trnh by phn ng th ca hirocacbon thm, hirocacbon no v hirocacbon khng no. HS (nhm 2) chun b, tho lun v a ra kt qu: Hirocacbon thm.

Khi c bt Fe, halogen th vo nhn thm, khi chiu sng halogen th vo nhnh. Nhm th c sn vng benzen quyt nh hng ca phn ng th tip theo. Hirocacbon no.
Khi chiu sng hoc un nng, clo th H C bc thp, brom th H C bc cao. Hirocacbon khng no.

nhit cao clo th H C bn cnh C lai ho sp2. Nguyn t H nhm CCH c th b thay th bi nguyn t Ag.
GV yu cu HS (nhm 3) trnh by phn ng cng ca hirocacbon thm, hirocacbon no v hirocacbon khng no. HS (nhm 3) chun b, tho lun v a ra kt qu: Hirocacbon thm.

Khi un nng c xc tc ph hp, aren cng vi H2 to thnh xicloankan. Khi c nh sng th benzen cng vi clo to hexacloran.

123

 Stiren c kh nng cng gc ankyl ging etilen. Hirocacbon no.

Ankan, xicloankan (tr xiclopropan v xiclobutan) khng c phn ng cng. Hirocacbon khng no. Anken, ankin d cng vi hiro, halogen, HA (A l halogen hoc OH) phn ng cng HA tun theo quy tc Mac-cp-nhi-cp. GV yu cu HS (nhm 4) trnh by HS (nhm 4) chun b, tho lun: phn ng oxi ho ca hirocacbon Hirocacbon thm. thm, hirocacbon no v hirocacbon Chy to nhit (c nhiu mui than). khng no. Vng benzen khng b oxi ho bi dung dch KMnO4, nhnh ankyl b oxi ho thnh COOH. Hirocacbon no.

Chy to nhit. Ch b oxi ho nhit cao hoc c thm xc tc. Hirocacbon khng no. Chy to nhit. D b oxi ho bi dung dch KMnO4 v cc cht oxi ho khc.
GV nhn xt, b sung kt qu ca mi nhm v chiu bng h thng y (SGK) ln mn hnh HS quan st, t c cch nh h thng.
II. bi tp Hot ng 2

GV chiu bi tp 1 (SGK) ln mn hnh HS tho lun. 1. Hy in nhng cm t cho di y vo cc ch trng trong cc cu sau: a) Phn t hirocacbon no ch c cc(1)bn vng, v th chng(2)
124

iu kin thng. Trong phn t(3)khng c(4)c bit no, nn khi tham gia phn ng th thng to ra(5)sn phm. b) (6)c nhng(7) l nhng(9) cho hirocacbon khng no. nhng(8)chng gy nn

c) vng benzen, 6 electron p to thnh(10)chung, do bn hn cc (11) ring r, dn n tnh cht c trng ca(12)l: tng i(13), kh cng, bn vng i vi tc nhn oxi ho. A: hirocacbon thm. B: hirocacbon khng no. C: Lin kt bi. D: lin kt . E: d th. H: trung tm phn ng. I: tng i tr. K: h lin hp . L: hirocacbon khng no. M: hn hp. N: phn ng c trng. HS tho lun v a ra kt qu: a) Lin kt / tng i bn tr v mt ho hc/ hirocacbon no/ trung tm phn ng / hn hp. b) Hirocacbon khng no/ lin kt / l trung tm phn ng / phn ng c trng c) H lin hp / lin kt ring r/ hirocacbon thm/ d th. GV chiu bi tp 2 (SGK) ln mn hnh HS tho lun. 2. Hy vit phng trnh phn ng ca toluen v naphtalen ln lt vi Cl2, Br2, HNO3, nu r iu kin phn ng v quy tc chi phi hng phn ng. HS tho lun v a ra kt qu:

Phn ng ca toluen H 2 C H Vi Cl2: + Cl2

H2CCl + HCl

benzyl clorua nu dng xc tc bt Fe phn ng th vo vng benzen. Vi Br2: CH3 Br + HBr CH3 + Br2
bt Fe

2-bromtoluen

CH3 + HBr Br 4-bromtoluen

125

 Vi HNO3:
CH3 + HNO3 (c)
H2SO4 c

CH3 NO2
2-nitrotoluen

H 2O

CH3 + NO2
4-nitrotoluen

H2O

Phn ng ca naphtalen. bt Fe

Br + Br2 + HBr NO2 + HNO3 H2SO4 c + H2O

GV chiu bi tp 3 (SGK) ln mn hnh HS tho lun. 3. Trong nhng cht sau : Br2, H2, HCl, H2SO4, HOH. Cht no trong iu kin no c th cng c vo ankylbenzen, vo anken? Vit phng trnh ho hc xy ra. Cho bit quy tc chi phi hng ca phn ng (nu c)? HS tho lun v a ra kt qu:

Anken anken + Br2 (dd) dn xut ibrom. anken + H2 (k) ankan.

anken + HCl (k) dn xut monoclo (Quy tc Mac-cp-nhi-cp). anken + H2SO4 (c) dn xut monohirosunfat (Quy tc Mac-cp-nhi-cp). anken + H2O dn xut ancol (Quy tc Mac-cp-nhi-cp).

Ankylbenzen Ankylbenzen + Br2 (dd) khng phn ng.

Ni Ankylbenzen + H2 (k) xicloankan.

Ankylbenzen + HCl khng phn ng. Ankylbenzen + H2SO4 (dd) khng phn ng. Ankylbenzen + H2O khng phn ng.
126

Th d:

Cl Cl + 3Cl2
nh sng

Cl Cl Cl

Cl + 3H2
Ni, t0

GV chiu bi tp 4 (SGK) ln mn hnh HS tho lun. 4. Hy dng phng php ho hc phn bit cc cht trong mi nhm sau: a) Toluen, hept-1-en v heptan. b) Etylbenzen, vinylbenzen v vinylaxetilen. HS tho lun v a ra kt qu: a) Dng dung dch KMnO4: Hept-1-en lm mt mu dung dch KMnO4 iu kin thng. Toluen lm mt mu dung dch KMnO4 khi un nng.

Heptan khng lm mt mu dung dch KMnO4.

b) Dng dung dch KMnO4: Vinylbenzen v vinylaxetilen lm mt mu dung dch KMnO4 iu kin thng. Etylbenzen khng lm mt mu dung dch KMnO4 iu kin thng. Dng AgNO3/NH3 nhn ra vinylaxetilen to kt ta mu vng. GV chiu bi tp 5 (SGK) ln mn hnh HS tho lun. 5. Khi cho stiren tc dng vi hiro c Pd xc tc 250C ch thu c etylbenzen. Mun thu c etylxiclohexan phi tin hnh phn ng 1002000C, p sut 100 atm. Hy vit phng trnh ho hc ca phn ng v gii thch. HS tho lun v a ra kt qu: Phn ng cng H2 vo vng benzen i hi nhit cao. CH=CH2 + H2 CH=CH2 + 4H2
Ni, 100-200 C 100 atm
0

CH2-CH3
Ni, t , p
0

CH2-CH3

127

GV chiu bi tp 6 (SGK) ln mn hnh HS tho lun. 6. a) sn xut cumen (isopropylbenzen) ngi ta cho benzen phn ng vi propen c xc tc axit. Hy vit phng trnh ho hc ca phn ng. b) sn xut 1,0 tn cumen cn dng ti thiu bao nhiu m3 (ktc) hn hp kh tch c t kh crackinh gm 60% propenv 40% propan (v th tch)? Bit rng hiu sut phn ng t 80%. c) Hy vit phng trnh ho hc ca phn ng khi c 1 mol cumen tc dng vi: 1 mol brom c mt bt Fe ; 1 mol brom c chiu sng HS tho lun v a ra kt qu: a) Phng trnh ho hc:
H C6H6 + CH2=CHCH3 C6H5CHCH3
+

(M = 120 g/mol)

CH3 10 .22, 4 = 0,187.106 (l) = 187 m3 120 C3H6 chim 60% hn hp nn th tch hn hp l: 187.100.100 = 389,58 (m3) 60.80
b) VC3H6 =
6

c) Vit phng trnh ho hc: CH3CHCH3 Br Br2

bt Fe, t0

CH3CHCH3 +

HBr

CH3CHCH3 + Br HBr

CH3CHCH3 + Br2
as

CH3CCH3 +

Br HBr

GV chiu bi tp 7 (SGK) ln mn hnh HS tho lun. 7. Nh my kh Dinh C c hai sn phm chnh: kh ho lng cung cp cho th trng, v kh t cung cp cho nh my in Ph M. a) Thnh phn chnh ca mi sn phm l g?

128

b) C nn chuyn tt c lng kh khai thc c thnh kh ga ho lng hay khng, v sao? HS tho lun v a ra kt qu: a) Kh ho lng: C3H8 v C4H10; kh t CH4. b) Khng nn, v CH4 c nhit si rt thp, phi lm lnh v nn p sut cao, Bnh thp phi c thnh dy nn khng kinh t. GV chiu bi tp 8 (SGK) ln mn hnh HS tho lun. 8. Du m hin ta ang khai thc c cha rt t benzen. Em chn phng n sn xut benzen no di y, v sao? Vit cc phng trnh ho hc ca phn ng xy ra :
1500 C xt,t C C2H2 C 6H 6 a) CH4
o o

rifominh b) Ankan C6C7 C6H6 + CH3C6H5

chng ct phn on

C6 H 6 C6H5CH3

HS tho lun v a ra kt qu: Chn phng n b) v ankan c nhiu trong du m, phng trnh ho hc xt,t o C6H5CH3 + 4H2 iu ch: C7H16 Bi tp ngh. 1. t chy hirocacbon A c hi H2O v CO2 theo th tch 1:1,75. Bit MA < 120 (vC) v A c th lm mt mu dung dch KMnO4 khi un nng. A l: A. etylbenzen B. toluen C. stiren D. propylbenzen p n B 2. Tnh thm l tnh: A. C mi thm c trng. B. D tham gia phn ng cng, kh tham gia phn ng th. C. D tham gia phn ng th, kh tham gia phn ng cng. D. D tham gia phn ng th v cng.
p n C. 3. em trng hp cc cht : butaien-1,3, propen, isopren, clopren. Sn phm trng hp ca cht no khng phi l cao su.

129

A. Butai-1,3-en C. Isopren

B. Propen D. Clopren

p n B 4. phn bit cc kh propen, propan, propin c th dng thuc th no sau y: C. Dung dch AgNO3/NH3. A.Dung dnh KMnO4. B. Dung dich Br2.. D. Dung dch Br2, dung dch AgNO3/NH3. p n D 5. Hy chn pht biu ng ?

A. Cc cht C2H2 , C3H4 , C4H6 l ng ng ca nhau. B. ng phn l nhng cht c cng khi lng phn t. C. Tt c anken u c ng phn hnh hc. D. Stiren lm mt mu nc brom nhit phng.
p n D. 6. X l mt hirocacbon mch h, l cht kh ktc. t chy hon ton m gam X thu c 17,6 gam CO2. Mt khc bit m gam X tc dng va vi dung dch cha 32 gam brom. Cng thc phn t ca X l: B. C2H4 hoc C4H6 A. C2H4 hoc C3H4 C. C3H6 hoc C4H6 D. C3H6 hoc C4H8 p n B.

130

Bi 50

thc hnh

Tnh cht ca mt s hirocacbon thm

A. Mc tiu bi hc 1. Kin thc

Bit c mc ch, cch tin hnh, k thut tin hnh mt s th nghim c th: Phn ng ca benzen, toluen vi dung dch thuc tm khi ngui v khi un nng. Tnh cht thng hoa ca naphtalen. Cng c kin thc v mt s tnh cht vt l, ho hc ca benzen v toluen.
2. K nng

Tip tc rn luyn k nng tin hnh v quan st th nghim ha hu c: S dng dng c, ho cht tin hnh c an ton, thnh cng cc th nghim trn. Quan st, m t hin tng, gii thch, vit cc phng trnh ho hc. Vit tng trnh th nghim.
3. Tnh cm, thi

Bit cch iu ch, t s dng hp l ho cht lng nh. Thng qua hot ng th nghim to nn hng th khi hc b mn ho hc.
B. chun b ca GV v HS

GV:

My tnh, my chiu, cc phiu hc tp. Ho cht: + Benzen. + Toluen. + Nc brom. + Hexan. + iot. + Dung dch KMnO4 1%. + Nc ct. + Du thng.
131

 Dng c:

+ ng nghim, n cn. + ng ht nh git. + Kp ho cht. + B gi th nghim.

HS:

n tp tnh cht ca benzen, toluen. Xem trc bi thc hnh.

C. tin trnh dy - hc Hot ng ca GV Hot ng 1 Dn d trc bui thc hnh Hot ng ca HS

GV nu cc ni dung chnh ca bui HS nghe GV trnh by v tho lun theo nhm thc hnh. thc hnh. Yu cu HS trnh by cc kin lin quan n bui thc hnh. Lu HS khi dng ho cht v s dng cn thn cc dng c th nghim. Chia lp hc thnh cc nhm thc hnh, mi nhm gm 45 HS.
I. Ni dung th nghim v cch tin hnh Hot ng 2 Th nghim 1. Tnh cht ca benzen

GV hng dn HS cc nhm lm th nghim nh SGK v lu HS: benzen l hp cht c hi, khng nn ngi hoc tip xc trc tip.

GV yu cu HS quan st hin tng.

HS lm th nghim theo cc bc: + Ly ba ng nghim nh nhau, mi ng cha 2ml nc brom. + Cho vo ng nghim th nht 5 git benzen, vo ng th hai 5 git du thng, vo ng th ba 5 git hexan. + Lc u v yn ba ng nghim. Hin tng:

132

+ Trong ng nghim th nht cht lng phn lm hai lp, lp trn dung dch c mu vng, lp di khng mu. + Trong ng nghim th hai nc brom b nht mu, lu s mt mu. + Trong ng nghim th ba cht lng phn lm hai lp, lp trn dung dch c mu vng, lp di khng mu ging ng nghim th nht. HS tho lun v tr li: GV hng dn HS gii thch bng cch a ra cc cu hi sau: Tnh cht vt l ca benzen. Kh nng ho tan cc cht ca benzen. Kh nng phn ng ca benzen vi nc brom. + ng nghim th nht: Benzen l cht lng, khng mu, nh hn nc, khng tan trong nc nn phn lp v nm pha trn. Benzen t phn cc nn ho tan tt brom hn nc, brom chuyn t pha nc vo pha cha benzen. Benzen khng phn ng vi brom trng thi dung dch v khng c xc tc. Nn lp cht lng pha trn c mu vng l brom tan trong benzen. + ng nghim th hai: Du thng l mt tecpen trong t nhin (pinen). Thnh phn ca du thng. Kh nng phn ng ca tecpen. Trong phn t c lin kt i C=C nn c kh nng phn ng vi nc brom to ra hp cht khng mu.

+ ng nghim th ba: Hexan l cht lng khng mu nh hn nc, khng tan trong nc nn phn lp v nm pha trn. Hexan cng t b phn cc nh Tnh cht vt l ca hexan. benzen v dung mi ho tan nhiu cht Kh nng ho tan cc cht ca km phn cc nh brom, iot hexan.

133

 Kh nng phn ng ca hexan vi nc brom. Hexan l ankan nn khng phn ng vi nc brom v vy c hin tng tng t nh benzen.
Hot ng 3 Th nghim 2. Tnh cht ca toluen

GV hng dn HS tin hnh th HS tin hnh th nghim: nghim. Ly ba ng nghim: ng nghim A cha mt t iot (bng ht tm), ng nghim B cha khong 2ml dung dch KMnO4 long, ng nghim C cha 2ml dung dch brom. Cho vo mi ng nghim 0,5 ml toluen. Lc k c ba ng nghim, yn vi pht. Yu cu HS quan st, nu hin tng Hin tng: v gii thch. C ba ng nghim u phn lm hai lp ng nghim A dung dch mu tm nu chng t iot tan tt trong toluen. ng nghim B lp toluen khng mu ni ln trn, dung dch KMnO4 khng b mt mu nm pha di. ng nghim C phn lm hai lp, lp trn c mu hung nht, lp dc khng mu. Gii thch: nh th nghim 1. GV yu cu HS un nng ng nghim HS tin hnh th nghim: B quan st hin tng xy ra. Gn ng nghim B ln gi. un nng ng nghim. GV gii thiu: Phng trnh ho hc Hin tng: Thy mu tm dung dch ca toluen vi KMnO4. b nht, dn dn chuyn sang mu nu
134

CH3 + 2KMnO4 t
0

COOK + 2MnO2 + KOH + H2O

nht sau chuyn thnh dung dch khng mu, ng thi xut hin kt ta nu en. HS ghi kt qu vo v th nghim.

Hot ng 3 II. Cng vic sau bui thc hnh

GV: Nhn xt v bui thc hnh v HS: thu dn, v sinh phng th nghim hng dn HS thu dn ho cht, ra cn thn, an ton. ng nghim v dng c th nghim, v sinh phng th nghim. GV: Yu cu HS lm tng trnh theo mu. HS lm tng trnh theo mu sau y: Ngy thng.nm. H v tn: Lp:. T th nghim:. Tng trnh ho hc bi s:. Tn bi:
Tn th nghim Phng php tin hnh Hin tng quan st Gii thch vit phng trnh phn ng

135

Chng VIII Dn xut Halogen. Ancol - Phenol

Bi 51

Dn xut halogen ca hirocacbon

A. Mc tiu bi hc 1. Kin thc

HS bit: Khi nim, phn loi dn xut halogen, ng phn, danh php. Tnh cht vt l v tnh cht ho hc c trng ca dn xut hirocacbon. Hot tnh sinh hc, ng dng ca mt s dn xut halogen. HS hiu: Tnh cht ho hc c bn: phn ng th nguyn t halogen (trong phn t ankyl halogennua, anlyl halogenua, phenyl halogenua) bng nhm OH. S lc c ch phn ng th. Phn ng tch hirohalogenua theo quy tc Zai-xep, phn ng vi magie.
2. K nng

Gi tn dn xut halogen theo hai cch n gin. Vit cng thc cu to v gi tn cc ng phn tng ng theo cng thc phn t. Vit phng trnh ho hc minh ho tnh cht ho hc v mt s ng dng. Phn bit mt s cht halogen c th. Gii bi tp tnh khi lng nguyn liu sn xut mt khi lng xc nh dn xut halogen, bi tp c ni dung lin quan.
3. Tnh cm, thi

Bn cnh nhng li ch em li cn bit cch s dng dn xut halogen trnh gy nhim mi trng v t bo v bn thn.
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B. chun b ca GV v HS

GV:

My tnh, my chiu, bng biu, cc phiu hc tp. Ho cht: ietyl ete, etyl bromua, bt Mg. Dng c: ng nghim, ng ht nh git, kp ng nghim.

HS: n tp kin thc v hirocacbon v xem trc bi dn xut halogen.

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I- Khi nim, phn loi, ng phn v danh php Hot ng 1 1. Khi nim

GV chiu bng sau ln mn hnh: Hiro CH4 CH2=CH2 C6H6

cacbon Dn CH3Cl, xut CH3Br, CH2=CHCl C6H5Cl halogen CHCl3

HS quan st v nhn xt:

Yu cu HS nhn xt v: Cng thc phn t ca cc dn xut hirocacbon trn vi hirocacbon tng ng. T rt ra khi nim dn xut halogen?

Cc dn xut trn u c thm nhng nguyn t halogen so vi hirocacbon tng ng trong phn t. Khi thay th nguyn t hiro ca phn t hirocacbon bng nguyn t halogen ta c dn xut halogen ca hirocacbon. GV: t hirocacbon, bng nhng cch HS tho lun v nhn xt: no ta c th thu c dn xut halogen Th nguyn t H ca hirocacbon: ca hirocacbon? Cho v d? as CH4 + Cl2 CH3Cl + HCl
500 C CH2=CHCH3+Cl2 CH2=CHCH2Cl
o

+ HCl Cng hirocacbon hoc halogen vo phn t hirocacbon khng no:

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GV b sung: Ngoi ra ta c th thu CH2=CH2+ HBr CH3 CH2Br c dn xut halogen bng cch thay CH2=CH2+Br2 CH2 CH2 th nhm OH ca ancol bng nguyn t Br Br halogen. V d: CH3CH2OH + HBr C2H5Br + H2O
Hot ng 2 2. Phn loi GV cho HS nghin cu SGK v yu cu: HS nhn xt: Nu c s phn loi dn xut C s phn loi: halogen? + Da vo cu to gc hirocacbon.

+ Da vo bn cht, s lng halogen. Nu cch phn loi dn xut halogen HS phn loi dn xut halogen: theo bn cht, s lng halogen. Cho v + Dn xut flo: CH3F, CHF3, C6H5F d minh ho? + Dn xut clo: CH Cl, CHCl ,
3 3

C2H5F... + Dn xut brom: CH3F, C6H5F, CH2=CHCl

CHF3,

+ Dn xut iot: CH3I, CH2=CHI + Dn xut cha ng thi mt vi halogen khc nhau: CH2FCl, CH2ClBr Nu cch phn loi dn xut halogen Da vo c im gc hiro cacbon: theo c im cu to gc hirocacbon. + Dn xut halogen ca hirocacbon Cho v d? no mch h: CH3Cl, CH2CH2 Cl Cl + Dn xut halogen ca hirocacbon khng no: CH2=CHCl, CH2=CHCH2Cl + Dn xut halogen ca hirocacbon thm: C6H5Cl, CH3C6H4Cl
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GV b sung: Da vo c im cu to gc hirocacbon, ngi ta cn phn loi dn xut halogen da vo bc ca dn xut halogen. Yu cu HS: Nu khi nim bc ca nguyn t C. Bc ca nguyn t C c tnh bng s lin kt ca no vi nguyn t C khc: Xc nh bc ca cc nguyn t C HS nhn xt v a ra p n. trong khung C sau: C C C CC C C C C C GV gii thiu: Bc ca halogen bng bc ca nguyn t C lin kt vi nguyn t halogen. Yu cu HS cho mt s v d. C C C C C C C C HS cho v d: Bc I: CH3CH2Cl Bc II: CH3CHClCH3 Bc III: (CH3)3CBr
I II III IV

Hot ng 3 3. ng phn, danh php a) ng phn

GV cho HS nghin cu SGK v yu cu HS tho lun v tr li. Nu khi nim ng phn. ng phn l nhng hp cht khc nhau nhng c cng cng thc phn Theo cng thc cu to th dn xut t. halogen c nhng kiu ng phn no? Da theo cng thc cu to c phn lm 2 nhm: ng phn nh hirocacbon. ng phn nhm chc. Vit cc ng phn cu to ca dn HS tho lun v a ra kt qu: xut halogen c cng thc phn t C4H9Cl. CH3 CH2 CH2 CH2Cl (I) CH3 CH2 CH Cl CH3 (II)

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CH3 CH CH2Cl CH3 CH3 CH3CCl CH3

b) Danh php

(III)

(IV)

GV cho HS nghin cu SGK v hng dn HS nhn xt v: Cch gi tn thng thng ca dn xut halogen. Cho v d minh ho.

HS nghin cu SGK v nhn xt: Tn thng thng gi tn ch c mt s t dn xut halogen: V d: CHCl3 clorofom CHBr3 bromofom CHI3 ioofom Tn thay th c cu to:

Cch gi tn thay th, cho v d.

S ch v tr halogen

Tn halogen

Tn mch chnh

V d: CH3CHCl2

1,1-icloetan

CH3 CH2 CH Cl 2-clobutan CH3 Br 1,3-ibrombenzen Cl Br 1-brom-4-clobenzen Br Cch gi tn gc chc. Tn gcchc c cu to:
Tn gc hirocacbon Tn halogenua

V d: CH2Cl2 CH2=CHF CH2=CHCH2Cl C6H5CH2Br

140

metylen clorua vinyl florua anlyl clorua benzyl clorua

Hot ng 4 II. Tnh cht vt l

GV cho HS nghin cu thng tin bng HS xem thng tin bi tp 3 rt ra (bi tp s 3 trang 215 SGK) yu cu nhn xt: HS rt ra nhn xt v: Trng thi ca dn xut halogen. Trng thi: iu kin thng, cc dn xut halogen c khi lng phn t nh nh CH3Cl, CH3Br l cht kh, cc dn xut c khi lng ln hn th lng hoc rn nh CHCl3, C6H5Cl Quy lut bin i nhit si. t0nc, t0s v khi lng ring tng theo chiu tng ca phn t khi. GV b sung: Dn xut halogen c tnh cht tng t ankan nhng khc mt s im sau: + Khng tan trong nc, thng nng hn nc v tan tt trong cc dung mi hu c. + Dn xut halogen thng c hot tnh sinh hc cao nh: CF3CHClBr2 khng c. DDT

halotan: cht gy m
HS ghi bi.

cht dit cn trng.

C6H6Cl6 thuc tr su 6.6.6.

III. Tnh cht ho hc

GV yu cu HS phn tch cu to ca HS phn tch cu to ca dn xut lin kt CX trong dn xut halogen? halogen da trn s sau: + CC X

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Do nguyn t halogen c m in GV yu cu HS d on tnh cht ca ln nn lm phn cc mnh lin kt CX. dn xut halogen. HS tho lun v d on: V lin kt CX phn cc nn n d b thay th nguyn t halogen bng nhm OH, tch phn t HX v phn ng vi Mg.
Hot ng 5 1. Phn ng th nguyn t halogen bng nhm OH

GV cho HS nghin cu SGK v yu cu HS nghin cu SGK v nhn xt: HS nhn xt: Cch tin hnh th nghim v kt Cch tin hnh th nghim. qu c trnh by trong bng sau: Kt qu th nghim. Du hiu kt ta AgCl. Kt lun iu kin c th cc cht trn c phn ng th nguyn t halogen, vit phng trnh ho hc minh ho. Dn xut halogen sch Cl Lc k gn ly lp nc axit ho bng HNO3 nh vo dd Agno3 un si vo nc gn ly lp nc, axit ho bng HNO3 nh vo dd AgNO3 un si vi dd NaOH gn ly lp nc, axit ho bng HNO3 nh vo dd AgNO3 propyl clorua Khng c kt ta Khng c kt ta C kt ta AgCl anlyl clorua Khng c kt ta C kt ta AgCl C kt ta AgCl clobenzen Khng c kt ta Khng c kt ta Khng c kt ta

Du hiu c AgCl kt ta chng t c phn ng th nguyn t Cl xy ra.

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 Kt lun: + Dn xut ankyl halogenua khng phn ng vi nc iu kin thng cng nh un si, nhng b thy phn khi un nng vi dung dch kim.
t C3H7Cl + OH C3H7OH + Cl
o

+ Dn xut anlyl halogen b thu phn ngay khi un nng vi nc:

t CH2=CHCH2Cl + H2O
o

CH2=CHCH2OH + HCl + Dn xut phenyl halogen khng phn ng vi dung dch kim nhit thng cng nh khi un nng m ch phn ng nhit v p sut cao:
p cao C6H5Cl + 2 NaOH o C6H5ONa + t cao

GV hng dn HS kt lun phn ng th nguyn t halogen.

NaCl + H2O

Kt lun: Phn ng th nguyn t halogen bng nhm OH d hay kh tu thuc ch yu vo bn cht ca dn xut halogen. S lc v c ch phn ng th nguyn t halogen

GV gii thiu s lc v c ch th HS nghe ging. nguyn t halogen. Halogen ni chung c dng: CC + X -

Lin kt CX l lin kt phn cc tu thuc vo bn cht ca halogen v iu kin thc hin m s th nguyn t halogen xy ra theo nhng c ch khc nhau. V d:

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Dn xut halogen no bc III di tc dng ca dung mi phn cc b phn li mc khng ng k. Giai on 1 (giai on chm) (CH3)3CBr U (CH3)3C+ + Br Giai on 2 (giai on nhanh) (CH3)3C+ + OH (CH3)3COH
Hot ng 6 2. Phn ng tch Hirohalogenua GV yu cu HS nghin cu th nghim HS tho lun v tr li. trong SGK v nhn xt: iu kin cn c mt baz rt mnh iu kin c phn ng tch. nh kim trong etanol v phi un si. Sn phm ca phn ng. Sn phm ca phn ng tu thuc vo

dn xut halogen (nu l dn xut mono halogen ca hirocacbon no mch h cho sn phm l anken). Kh nng tch ca halogen. Kh nng tch ca halogen c minh ho bng s sau: CH3 CH CH CH2 H Cl H Nguyn t halogen tch vi nguyn t hiro ca nguyn t cacbon lin kt trc tip vi nguyn t cacbon c nguyn t halogen. Phng trnh ho hc minh ho:
kim/ancol CH2CH2 o H2=CH 2 + HX t

Vit cc phn ng minh ho.

GV: tng t, yu cu HS vit phng HS c 2 sn phm: trnh ho hc tch ca dn xut c cng CH3CH CH CH2 thc CH3CH2CHClCH3 c nhng sn phm H Cl H no?(khng k ng phn hnh hc).

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kim/ ancol t0

CH3CH=CHCH3 + HCl
sn phm chnh

CH3CH2CH=CH2 + HCl
sn phm ph

Bit sn phm th nht l sn phm HS nu quy tc tch Zai-xep: Nguyn t chnh, sn phm th hai l sn phm halogen s tch cng H lin kt vi cacbon bc cao hn l sn phm chnh. ph, vy nu quy tc tch ca Zai-xep.
Hot ng 7 3. Phn ng vi magie GV lm th nghim: HS quan st v nu hin tng. Cho Mg vo ng nghim ng ietyl Bt Mg hu nh khng b bin i, ete (C2H5OC2H5) khan, khuy mnh, chng t Mg khng tan trong ietyl ete. yu cu HS nu hin tng. Gii thch. Tip tc cho t t etyl bromua vo Bt Mg dn dn tan ht, chng t c ng nghim, lc u, yu cu HS quan phn ng gia etyl bromua vi Mg sinh st, nu hin tng. ra cht mi tan c trong dung mi GV hng dn HS gii thch v vit ietyl ete. phng trnh ho hc. Phng trnh ho hc:
ete khan C2H5MgBr C2H5Br + Mg

GV b sung: Sn phm etyl magie bromua c lin kt gia C v Mg kim loi (CMg) nn gi l hp cht c kim (c magie). Lin kt ny l trung tm ca cc phn ng tip theo.
Hot ng 8 IV. ng dng

GV su tp cc tranh nh, mu vt, phim c lin quan n ng dng ca cc dn xut halogen chiu ln mn hnh cho HS quan st. Yu cu HS tng kt cc ng dng chnh.

HS: Dn xut halogen ca hirocacbon c cc ng dng c bn sau: a) Lm nguyn liu cho tng hp hu c: + Vinylclorua tng hp nha PVC. + CH2=C CH=CH2 tng hp cao su Cl cloropren
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+ CF2 = CF2 tng hp teflon. + Tng hp ancol, phenol. b) Lm dung mi: 1,2-icloetan, clorofom c) Cc lnh vc khc: Thuc tr su, dit cn trng. Thuc gy m. GV lu cho HS : Ho cht thng c v gy nhim mi trng. Mun dng ho cht trong i sng v sn xut phi nm vng tnh cht v s dng theo ng hng dn ca cc nh chuyn mn.
Hot ng 9 Cng c bi v bi tp v nh 1. Cng c bi.

GV khc su mt s kin thc cho HS v: Danh php ca dn xut halogen. Tnh cht vt l v hot tnh sinh hc ca mt s dn xut halogen. Phn ng th, phn ng tch theo quy tc tch Zai-xep. Phng php iu ch v ng dng ca dn xut halogen. GV chiu cc bi tp sau ln mn hnh HS tho lun. 1. un si hn hp gn C2H5Br v KOH d trong C2H5OH, sau khi phn ng xy ra hon ton, dn kh sinh ra qua dung dch brom d, thy c 8 gam brom tham gia phn ng. Khi lng C2H5Br em phn ng l: A. 14,00 gam C. 5,450 gam B. 2,725 gam D. 10,900 gam

p n C. 2. C bao nhiu dn xut C4H9Br tc dng vi KOH d trong C2H5OH, trong mi trng hp ch to ra mt anken duy nht. A. Mt cht B. Hai cht C. Ba cht D. Bn cht p n C
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2. Bi tp v nh: 1, 2, 3, 4, 5, 6, 7, 8 (SGK) D. Hng dn gii bi tp SGK 1. Gi tn theo hai cch bc ca dn xut halogen:

a) CH3I: Metyl ioua (tn gc-chc), ioometan (tn thay th), bc I. CHI3: ioofom (tn thng thng), triioometan (tn thay th), bc I. BrCH2CH2CH2CH2Br: 1,2-ibrombutan (tn thay th), buta-1,4-iyl bromua (tn gc-chc), bc I. CH3CHFCH3: 2-flopropan (tn thay th), isopropyl florua (tn gc-chc), bc II. (CH3)2CClCH2CH3: 2-clo-2-metylbutan (tn thay th), tert-pentyl clorua (tn gc-chc), bc III. b) CH2=CHCH2Br: 3-bromprop-1-en (tn thay th), anlyl bromua (tn gcchc), bc I. C6H5CH2I: iotphenylmetan (tn thay th), benzyl ioua (tn gc-chc), bc I. p-FC6H4CH3: 1-flo-4-metylbenzen (tn thay th), p-tolyl-florua (tn gc-chc), bc II. o-ClC6H4CH2CH3: 1-clo-2-etylbenzen (tn thay th), o-etyl phenylen clorua (tn gc-chc), bc II. m-F2C6H4: 1,3-iflobenzen (tn thay th), m-phenylen iflorua (tn gc-chc), bc II. 2. Cng thc cu trc ( cng thc lp th) v tn cc ng phn tng ng vi cng thc phn t. a) C2H2ClF; b) C3H5Cl. a) C2H2ClF H Cl H H C=C C=C H F Cl F cis-1-clo-2-floeten trans-1-clo-2-floeten CH2=CClF b) C3H5Cl H 3C H C=C Cl H 3C 1-clo-1-floeten H H C=C Cl H

cis-1-cloprop-1-en

trans-1-cloprop-1-en

CH2=CClCH3

2-cloprop-1-en

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3. a) S bin i nhit si theo quy lut:

nhit thng cc dn xut CH3F, CH3Cl, CH3Br, l cht kh, CH3I l cht lng. Nhit si ca dy tng khi X ln lt c thay bng Cl, Br, I. Nhit si ca dy tng khi s nguyn t X tng. Nhit si tng khi gc ankyl tng mch cacbon, Nhit si ca phenyl halogenua cao hn ankyl halogenua. b) Nhit si ca cc dn xut halogen cho trong bng cao hn nhit si ca hirocacbon tng ng. Th d: CH4 (ts= 1620C) CH3F (ts= 780C) C2H6 (ts= 890C) C2H5Cl (ts= 120C) C2H5Cl (ts= 710C) C3H8 (ts= 420C) C6H6 (ts= 860C) 4. a) D ; b) B ;
5. a) Cc phng trnh ho hc:
t CH3CHBrCH2CH3 + NaOH CH3CHOHCH2CH3 + NaBr o

C2H5Cl (ts= 1320C) c) A ; d) C.

CH3CH CH CH2 H Cl H

kim/ ancol t0

CH3CH=CHCH3 + HCl
Sn phm chnh

CH3CH2CH=CH2 + HCl
Sn phm ph

6. a) CH2=CH2 + Cl2 CH2ClCH2Cl

CH2ClCH2Cl + 2NaOH CH2=CHCl + NaCl + H2O

HCl,HgCl 2 n CH2=CHCl o 150-200 C

CH2CH
Cl

1500 C b) 2CH4 C 2H 2 +

3H2 CH2CH Cl
n

HgCl 2 CH2 = CHCl CH CH + HCl

n CH2=CHCl

HCl,HgCl2 o 150-200 C

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xt,t c) 2CH CH CH CCH=CH2

o

CH CCH=CH2 + HCl CH2=CHClCH=CH2

xt,t (CH2CHCl=CHCH2)n nCH2=CHClCH=CH2
o

cao su cloropren Hin nay PVC c tng hp theo s :

+Cl2 nhit phn trng hp C2H4 ClCH2CH2Cl CH2=CHCl PVC

7. Phn bit cc cht sau bng phng php ho hc:

a) hexyl bromua, brombenzen, 1-brombut-2-en C6H5Br (2) BrCH2CH=CHCH3 (3) CH3[CH2]5Br (1) Ln lt cho cc cht (1), (2), (3) em un si vi nc, gn ly lp nc, axit ho bng HNO3, nh vo dung dch AgNO3, ch trong ng th ca cht (3) thuc loi anlyl halogenua c kt ta AgCl, do vy nhn ra cht (3). Ln lt cho cc cht (1), (2), em un si vi NaOH, gn ly lp nc, axit ho bng HNO3, nh vo dung dch AgNO3, ch trong ng th ca cht (1) thuc loi ankyl halogenua c kt ta AgCl, do vy nhn ra cht (1). Cn li l cht (2). b) 1-clopent-2-en, pent-2-en, BrCH2CH=CHCH2CH3 (1) CH3CH=CHCH2CH3 (2) 1-clopentan CH3[CH2]4Cl (3)

Ln lt cho cc cht (1), (2), (3) em un si vi nc, gn ly lp nc, axit ho bng HNO3, nh vo dung dch AgNO3, ch trong ng th ca cht (1) thuc loi anlyl halogenua c kt ta AgCl do vy nhn ra cht (1). Ln lt cho cc cht (2), (3) em un si vi NaOH, gn ly lp nc, axit ho bng HNO3, nh vo dung dch AgNO3, ch trong ng th ca cht (1) thuc loi ankyl halogenua c kt ta AgCl do vy nhn ra cht (1). Cn li l cht (2).
8. a) Cc phng trnh ho hc:

CH2=CH2 + Cl2 CH2ClCH2Cl

500 C CH2=CHCl + CH2ClCH2Cl
o

HCl

4HCl + O2 Cl2 + 2H2O b) u im so vi cc s iu ch PVC khc (s cu 6) l: Tn dng Cl2, Cht thi l H2O nn khng gy nhim mi trng. Khng dng NaOH, etanol.
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c)

CH2=CH2 + Cl2 CH2ClCH2Cl

t CH2=CHCl + HCl CH2ClCH2Cl
o

(*)

n CH2=CHCl

HCl,HgCl2 150 200o C

CH2CH Cl
n

T ba phng trnh ho hc trn ta rt ra s . n CH2=CH2 CH2CH n mol x mol Cl n 1 mol 1.000.000 mol 62,5

x= 16000mol Hay 16000. 22,4 = 358400 (lt) C2H4 ktc. Theo phng trnh (*) th s mol Cl2 bng s mol C2H4, th tch Cl2 bng th tch C2H4.

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Bi 52

luyn tp Dn xut halogen

A. Mc tiu bi hc 1. Kin thc

Cng c, h thng ho tnh cht ho hc v phng php iu ch dn xut halogen. HS bit:

ng dng ca dn xut halogen trong tng hp hu c v trong thc t. Cc phng php iu ch dn xut halogen.

HS hiu:
Phn ng th v phn ng tch ca dn xut halogen. Kh nng th khc nhau ca cc dn xut halogen.
2. K nng

Vn dng cc tnh cht ca dn xut halogen gii thch hin tng lin

quan n l thuyt v thc t.

Vn dng kin thc hc t bit cch gii ng bi tp. Bit lp k hoch gii mt bi ton ho hc.
3. Tnh cm, thi thc cn thn, trung thc, kin tr, chnh xc trong hc tp ho hc. B. chun b ca GV v HS

GV: My tnh, my chiu, h thng cc cu hi v bi tp n tp. HS: n tp cc kin thc v dn xut halogen.

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C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I. Kin thc cn nm vng Hot ng 1 1. Phn ng th

GV nu cc vn c bn hc:
Khi nim dn xut halogen. c im cu trc lin kt CX

trong dn xut halogen.

Tnh cht ho hc c bn ca dn xut

halogen.
Quy tc tch Zai-xep.

GV chia HS theo cc nhm (5 nhm) v giao ni dung luyn tp cho cc nhm. GV yu cu HS (Nhm 1) cho bit HS nu iu kin v vit phng trnh iu kin xy ra phn ng th nguyn ho hc. t halogen bng nhm OH ca dn + Dn xut ankyl halogenua khng xut loi ankyl halogenua. Vit phn ng vi nc iu kin thng phng trnh ho hc. cng nh un si, nhng b thy phn khi un nng vi dung dch kim.
t C3H7Cl + OH C3H7OH + Cl
o

GV yu cu HS (Nhm 2) cho bit HS nu iu kin v vit phng trnh iu kin xy ra phn ng th nguyn ho hc. t halogen bng nhm OH ca dn + Dn xut anlyl halogenua b thu xut loi anlyl halogenua. Vit phng phn ngay khi un nng vi nc. trnh ho hc. to CH =CHCH Cl + H O
2 2 2

CH2=CHCH2OH + HCl

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GV yu cu HS (Nhm 3) cho bit iu kin xy ra phn ng th nguyn t halogen bng nhm OH ca dn xut loi phenyl halogenua v vinyl halogenua. Vit phng trnh ho hc.

HS nu iu kin v vit phng trnh ho hc. + Dn xut phenyl halogen v vinyl halogenua khng phn ng vi dung dch kim nhit thng cng nh khi un nng m ch phn ng nhit v p sut cao.
p cao C6H5ONa + C6H5Cl + 2 NaOH t o cao

NaCl + H2O GV yu cu HS (Nhm 4) cho bit HS nu iu kin v vit phng trnh iu kin xy ra phn ng tch hiro ho hc: halogenua khi dn xut halogenua. Dn xut halogen ch b tch HX khi Vit phng trnh ho hc. un nng dch kim trong ancol. Sn phm to thnh cha lin kt bi. CH3CH CH CH2 H
kim/ ancol t0

Cl H CH3CH=CHCH3+HCl CH3CH2CH=CH2+HCl
Sn phm ph Sn phm chnh

GV yu cu HS (nhm 5) nu quy tc HS nu quy tc tch Zai-xep: tch ca Zai-xep. Nguyn t halogen s tch cng nguyn t H lin kt vi cacbon c bc cao hn l sn phm chnh.
Hot ng 2 II. Bi tp

GV chun b cc bi tp t chn hoc bi tp SGK HS luyn tp. GV chiu bi tp 1 (SGK) ln mn hnh HS tho lun.
1. a) Hy thit lp biu thc tnh gi tr ( +v) i vi dn xut halogen (xem bi tp 1 bi 44). b) Tnh (+v) i vi cc cht sau: C6H6Cl6, C5H5Cl, C8H5Br3, C12H4Cl4O2. HS tho lun a ra kt qu:
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Cng thc dn xut halogen CxHyClu C6H6Cl6 C6H5Br

S nguyn t H t hn ankan tng ng 2x + 2 y 8 9

S nguyn t halogen (u) 6 1

S lin kt 0 3

S vng Tng s + v v 1 1 1 4

Qua bng trn ta rt ra biu thc tnh gi tr + v i vi dn xut halogen: 1 + v = [2x + 2 (y + u)] 2 Cng thc trn khng ph thuc vo nguyn t ho tr 2 nh oxi 1 b) p dng 1: C6H6Cl6 c + v = [2.6 + 2 (6 + 6)] = 3 2 1 p dng 2: C5H5Cl c + v = [2.5 + 2 (5 + 1)] = 1 2 1 p dng 3: C12H4Cl4O2 c + v = [2.12 + 2 (4+ 4)] = 9 2 1 p dng 4: C8H5Cl3 c + v = [2.8 + 2 (5 + 3)] = 5 2 GV chiu bi tp 2 (SGK) ln mn hnh HS tho lun.
2. a) Trong hai lin kt CCl v HCl lin kt no phn cc hn? V sao ?

b) V sao dn xut halogen hu nh khng tan trong nc m tan tt trong dung mi hu c nh : hirocacbon, ete, ancol?
HS tho lun a ra kt qu:

a) m in: C = 2,55; H = 2,20; Cl =3,16. Hiu m in trong CCl l 3,16 2,55= 0,61. Hiu m in trong HCl l 3,16 2,20= 0,96. Vy lin kt trong HCl phn cc hn lin kt trong CCl. b) Cc dn xut halogen u l hp cht cng ho tr nn thc t khng tan trong nc, chng tan c trong dung mi hu c v bn thn dn xut halogen cng l dung mi hu c tt.
GV chiu bi tp 3 (SGK) ln mn hnh HS tho lun. 3. Cho cc hp cht sau: 2-clobutan, vinyl bromua, benzyl clorua.

a) Hy vit cng thc cu to v dng cc mi tn thng, mi tn cong ch chiu di chuyn mt electron cc nhm chc ca cc hp cht .
154

b) Hy vit phng trnh nu xy ra phn ng ca tng hp cht cho cu a) ln lt vi cc tc nhn sau: C. KOH/butanol/ t0. A. Mg/ete B. NaOH/H2O/t0 HS tho lun a ra kt qu: CH2 Cl H H H H .. H C C C C H CH2 = CH Br H Cl H H b) Phn ng vi Mg/ete khan : H CH3C Cl H + Mg CH3CMgCl
ete

C 2H 5 C 2H 5 ete CH2=CHMgBr CH2 = CH Br + Mg C6H5CH2 Cl H CH3C Cl + Mg C6H5CH2MgCl

ete

(phn ng km)

Phn ng vi NaOH/ H2O/t0:

H + NaOH CH3COH
H 2 O,t o

+ NaCl

C2 H 5 C2 H 5 CH2 = CH Br + NaOH: Khng phn ng vi dung dch NaOH un nng. C6H5CH2 Cl

H 2 O,t + NaOH C6H5CH2OH + NaCl
o

Phn ng vi KOH/ butanol/t0:

H H H H H C C C C H H Cl H H

KOH, C4H9OH, t0 - HCl

CH3-CH=CHCH3
sn phm chnh

C6H5CH2Cl

KOH, C4H9OH, t0 - KCl

CH2=CH CH2CH3 C6H5CH2OH

sn phm ph

GV chiu bi tp 4 (SGK) ln mn hnh HS tho lun. 4. Khi un si dung dch gm C4H9I, etanol v KOH ngi ta thu c ba anken m khi hiro ho chng th u nhn c butan. Hy vit s phn ng to ra cc anken v cho bit anken no l sn phm chnh, ph. HS tho lun a ra kt qu:

S phn ng:
155

CH2=CHCH2CH3 CH3CHICH2CH3
xt, to

but-1-en cis-but-2-en

H3C C=C H H C=C

CH3 H CH3 trans-but-2-en (sn phm chnh)

- HI

H3C H GV chiu bi tp 5 (SGK) ln mn hnh HS tho lun. 5. Cho cc ho cht sau: etanol, axit axetic, etyl clorua, axit sunfuric, natri hiroxit v mangan ioxit. a) Hy ngh mt s phn ng n gin nht iu ch 1,2-icloetan. b) Hy tnh xem iu ch 49,5g 1,2-icloetan th cn dng bao nhiu gam mi cht trong s phn ng ngh (coi hiu sut cc phn ng u t 100%). HS tho lun a ra kt qu: a) T cc ho cht: Etanol, axit axetic, etyl clorua, axit sunfuric, natri hiroxit v mangan ioxit. Cc phn ng iu ch:
C 2 H5 OH,t CH2=CH2 CH3CH2Cl + NaOH
o

+ NaCl + H2O

t 2NaCl + H2SO4 Na2SO4 + 2HCl to 4HCl + MnO2 MnCl2 + Cl2 + 2H2O CH2=CH2 + Cl2 CH2ClCH2Cl
o

b) Coi hiu sut cc phn ng l 100% nn ta c: 49,5 S mol ca CH2ClCH2Cl l n = = 0,5 mol. 99 S mol cc cht l: CH3CH2Cl + NaOH CH2=CH2 + NaCl + H2O 2 mol
to

2 mol 2 mol

2 mol

2 mol

2NaCl + H2SO4 Na2SO4 + 2HCl 2 mol 1 mol

o

t MnCl2 + Cl2 + 2H2O 4HCl + MnO2 2 mol 0,5 mol 0,5 mol CH2=CH2 + Cl2 CH2ClCH2Cl

0,5mol

0,5 mol

0,5 mol

Khi lng cc cht cn dng l:

156

2 mol C2H5Cl hay khi lng l: 64,5 gam C2H5Cl. 2 mol NaOH hay khi lng l: 80 gam NaOH. 1 mol H2SO4 hay khi lng l: 98 gam H2SO4. 0,5 mol MnO2 hay khi lng l: 43,5 gam MnO2. GV chiu bi tp 6 (SGK) ln mn hnh HS tho lun. 6. iu ch cloropren (2-clobuta-1,3-ien), ngi ta ime ho axetilen ri cho sn phm thu c phn ng vi HCl. a) Hy vit phng trnh ho hc ca cc phn ng xy ra v cho bit sn phm trong mi giai on c to ra nh th no ? b) Vit phng trnh ho hc ca phn ng trng hp cloropren, gi tn sn phm v cho bit ng dng ca n. HS tho lun a ra kt qu:
xt,t a) 2HCCH CH2=CHCCH
o

CH2=CHCCH + HCl

CH2=CHCCl=CH2 Sn phm chnh v vn gi c h lin hp bn CH3CHClCCH Sn phm ph v ph v c h lin hp nn khng bn

xt,t b) nCH2=CHCCl=CH2 (CH2CH=CClCH2)n

o

cloropren

policloropren

2-clobuta-1,3-ien dng lm cao su GV chiu bi tp 7 (SGK) ln mn hnh HS tho lun. 7. Hy ngh s cc phn ng k tip nhau thc hin c cc chuyn ho sau: a) CH3CH2CH2CH2Cl CH3CHClCH2CH3 b) C6H6 C6H5CCl2CH3 HS tho lun a ra kt qu: a) CH3CH2CH2CH2Cl CH3CH2CH=CH2 + HCl but-1-en CH3CH2CHClCH3 sn phm chnh CH3CH2CH2CH2Cl sn phm ph
157

CH3CH2CH=CH2 + HCl

b) C6H6 C6H5CHClCH2Cl CH2CH3 C6H6 + CH2=CH2 CH2CH3

ZnO, 600 C
0

axit

CH=CH2 + H2 CH CH2 Cl Cl

CH=CH2

+ Cl2

GV chiu bi tp 8 (SGK) ln mn hnh HS tho lun. 8. Hy in ch (ng) hoc S (sai) vo cc du [ ] mi cu sau:

a) Sn phm chnh khi monoclo ho isopentan l dn xut clo bc III. [ ] b) Sn phm chnh khi monobrom ho isopentan l dn xut clo bc III. [ ] c) Sn phm chnh khi chiu sng hn hp toluen v clo l p-clotoluen. [ ] HS tho lun a ra kt qu: a) S. V clo th ch H cacbon c cc bc khc nhau. b) . V brom hu nh ch th cacbon bc cao. c) S. V sn phm chnh l but-2-en. d) S. V khi chiu sng th th nhnh, khng th nhn benzen.

158

Bi 53

Ancol cu to, danh php, tnh cht vt l

A. Mc tiu bi hc 1. Kin thc

HS bit:

Khi nim, phn loi, cu to phn t ancol. Lin kt hiro, tnh cht vt l ca ancol. Vit ng phn v gi tn ca cc ancol.
HS hiu:

S nh hng ca lin kt hiro n tnh cht vt l ca ancol.

2. K nng

T cng thc bit gi tn v ngc li t gi tn vit c cng thc nhng

ancol n gin.

Vn dng lin kt hiro gii thch mt s tnh cht vt l ca ancol.

3. Tnh cm, thi

Ancol l ho cht thng dng trong cuc sng. Nghin cu tnh cht vt l s to s hng th cho HS khi nghin cu v hp cht hu c c nhm chc.
B. chun b ca GV v HS

GV:

My tnh, my chiu, cc phiu hc tp. Bng biu, phn mm.

HS: n tp kin thc v dn xut halogen v xem trc bi ancol.

159

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I. nh ngha, Phn loi, ng phn v danh php Hot ng 1 1. nh ngha GV chiu ln mn hnh mt s ancol HS rt ra im ging nhau: bit: CH3OH, C2H5OH, C3H7OH Yu u c nhm OH lin kt trc tip cu HS nhn xt v im ging nhau v vi gc hirocacbon. cu to ca cc hp cht hu c trn. HS nu nh ngha: T nu khi nim ancol. Ancol l hp cht hu c m trong GV ghi nhn pht biu v chnh sa li, phn t c nhm hiroxyl (OH) lin nhc HS lu : Nhm hidroxyl (OH) kt trc tip vi nguyn t cacbon no. lin kt trc tip vi nguyn t cacbon no. V d: CH3OH, C6H5CH2OH Hot ng 2 2. Phn loi GV cho HS nghin cu thng tin bng HS da vo 2 c s l: 8.2 SGK v yu cu: + Cu to gc hirocacbon. Nu c s phn loi ancol? + S lng nhm OH

GV gi 2 HS trnh by cch phn loi HS 1: Phn loi ancol theo gc hirocacbon theo gc v theo s lng nhm OH. Ancol no: V d CH3OH, C2H5OH.. Ancol khng no: V d CH2= CH CH2OH

Ancol thm: V d C6H5CH2OH

HS 2: Phn loi ancol theo s lng nhm hiroxyl. Ancol n chc: C2H5OH, C3H7OH Ancol a chc: C3H5(OH)3,

GV yu cu HS nu khi nim bc ancol.

160

GV chiu ln bng mt s ancol c bc C2H4(OH)2 khc nhau: HS 2: Bc ancol l bc ca C lin kt CH3 C2H5OH , CH3CHOH, CH3C OH vi nhm OH. HS xc nh bc ca cc ancol CH CH3 CH3 3 Yu cu HS xc nh bc ca cc C2H5OH CH3CHOH CH3C OH ancol. CH3 CH3 BcI Bc II Bc III
II. ng phn, danh php Hot ng 3 1. ng phn

GV cho HS nghin cu SGK v yu HS tho lun v tr li: cu: Nu khi nim ng phn. Nhng hp cht khc nhau nhng c cng cng thc phn t c gi l cc ng phn ca nhau. Ancol c:
ng phn cu to gc hirocacbon. ng phn v tr nhm OH.

Ancol c nhng loi ng phn no?

Vit cc ng phn ca C4H9OH.

Vit c 4 ng phn CH3 CH2 CH2 CH2OH (I) CH3 CH2 CH OH (II)
CH3 CH3 CH CH2OH CH3 CH3 CH3COH (III)

(IV)

Trong cc ng phn trn ng phn no l ng phn mch, ng phn no l ng phn v tr?

CH3 I v II, III v IV l ng phn v tr. I v III, II v IV l ng phn mch.

161

Hot ng 4 2. Danh php

GV cho HS nghin cu (SGK), hng HS tho lun: dn HS tho lun, rt ra cch gi tn thng thng v tn thay th. Yu cu HS nhn xt v: Cu to tn thng thng. a) Tn thng thng ca ancol c cu to:

Gi tn cc ancol C4H9OH theo tn HS vit ng phn v gi tn: thng thng. CH3CH2CH2CH2O Hancol butylic CH3CH2CHOH ancol sec-butylic
CH3 CH3CH CH2OH CH3 CH3 CH3COH ancol tert-butylic ancol isobutylic

Ancol

tn gc ankyl

ic

Cu to tn thay th.

CH3 b) Tn thay th c cu to: Tn hirocacbon tng ng vi mch chnh

+ Cch chn mch chnh. + Cch nh s.

s ch v tr nhm OH

ol.

+ Mch chnh l mch C di nht lin kt vi nhm OH. + nh s th t nguyn t C mch chnh t pha gn nhm OH hn. Gi tn cc ancol C4H9OH theo tn HS gi tn. thay th CH3CH2CH2CH2OH butan-1-ol CH3 CH2CHOH butan-2-ol CH3

162

CH3CHCH2OH 2-metylpropan-1-ol CH3 CH3 CH3COH CH3 GV b sung tn gi mt s ancol khc: CH2CHCH2 CH2CH2 OH OH OH OH OH etan-1,2-iol propan-1,2,3-triol (etilenglicol) (glixerol) CH2=CHCH2OH prop-2-en-1-ol (ancol anlylic)
III. Tnh cht vt l v lin kt hiro ca ancol Hot ng 5 1. Tnh cht vt l GV cho HS quan st mu ancol etylic v lm th nghim ho tan vo nc. Yu cu HS rt ra nhn xt v tnh cht vt l ca ancol etylic. HS quan st v nhn xt: Ancol etylic l cht lng, khng mu, tan tt trong nc, d bay hi GV tng kt li tnh cht vt l ca ancol etylic. Chiu bng 8.3 SGK cho HS quan st HS xem thng tin trong bng v nhn (hoc cho HS nghin cu thng tin trong xt. bng 8.3). Yu cu HS nhn xt v: Trng thi ca ancol iu kin thng. Quy lut bin i tan khi s nguyn Cc ancol l cht lng iu kin t C tng. thng.

2-metylpropan-2-ol

163

 Quy lut bin i nhit si khi s tan ca cc ancol gim dn khi nguyn t C tng. phn t khi tng dn. Khi lng ring. Nhit si ca cc ancol tng dn khi phn t khi tng dn. Khi lng ring ca ancol u dy ng ng nh hn nc. GV b sung: HS kim tra kin ca mnh ng hay iu kin thng ch c cc ancol sai v t b sung thm cc t liu. t CH3OH n khong C12H25OH l cht lng, cc ancol ln hn l cht rn. Cc ancol c t 1-3 nguyn t C trong phn t tan v hn trong nc. Cc poliol thng snh, nng hn nc v c v ngt. Cc ancol l nhng cht khng mu.

Hot ng 6 2. Lin kt hiro a) Khi nim v lin kt hiro

GV Chiu bng 8.4 SGK ln mn hnh HS nghin cu thng tin v tho lun. cho HS quan st nhit nng chy, nhit si v tan ca mt s cht.
CH3F CH3OCH3 C 2H 6
M,g/mol tnc, C t s, oC tan
o

CH3OH
32 98 65

30 172 89 0.007

34 142 78 0.25

46 138 24 7,6

HS nhn xt: Yu cu HS nhn xt v: S chnh lch khi lng phn t ca Khi lng ca cc cht trong bng cc cht trn so vi metanol. chnh lch khng nhiu so vi CH3OH.
164

 S chnh lch nhit si, nhit nng chy, tan ca cc cht trn so vi metanol. GV t vn : Ti sao li c s chnh lch nh vy? GV hng dn HS gii quyt vn So snh s phn cc nhm COH ca ancol vi phn t nc.

Nhit si, nhit nng chy, tan ca ancol cao hn nhiu so vi hirocacbon, dn xut halogen v ete.

HS so snh s phn cc di s iu khin ca GV.

0

O
105

O
104,50

ancol

nc

Nguyn t H ca nhm OH ny v Khi nguyn t H mang in tch (+) nguyn t O ca nhm OH kia c nh ca nhm OH ny v nguyn t O mang in tch () ca nhm OH kia gn hng n nhau khng ? nhau th to thnh lin kt yu.
GV b sung: Lin kt yu gi l lin HS nghe ging v ghi chp. kt hiro. Bn cht ca lin kt hiro l lc ht tnh in gia nguyn t H mang in tch dng vi nguyn t mang in tch m (thng l nguyn t c m in ln nh : oxi, clo, flo, nit). GV c th chiu mt s dng lin kt hiro cho HS quan st(hnh 8.3) Lin kt hiro ca nc:

Lin kt hiro ca ancol:

Lin kt hiro ca ancol vi nc:

165

b) nh hng ca lin kt hiro n tnh cht vt l

GV cho HS nghin cu SGK v yu cu HS nghin cu SGK v nhn xt: nhn xt v s nh hng ca lin kt Do c lin kt hiro gia cc phn t hiro n tnh cht vt l. vi nhau, cc phn t ancol ht nhau mnh hn so vi nhng phn t c khi lng xp x nhau, nhng khng c lin kt hiro (nh: ete, hirocacbon, dn xut hologen). V th cn phi cung cp nhiu nng lng hn chuyn ancol t trng thi rn sang trng thi lng (nng chy), cng nh t trng thi lng sang trng thi kh (si). Cc phn t ancol c phn t khi nh mt mt c s tng ng vi cc phn t nc (nh phn tch), mt khc li c kh nng to lin kt hiro vi nc nn c th xen gia cc phn t nc, gn kt vi cc phn t nc. V th chng ho tan tt trong nc.
Hot ng 7 Cng c bi v bi tp v nh 1. Cng c bi GV khc su mt s kin thc cho HS v:

Cng thc chung ca ancol. Cu to ca ancol c lin kt OH phn cc. Cc loi ng phn ca anken, quy tc gi tn ancol. Ancol c nhit si cao hn hirocacbon tng ng do ancol c lin kt hiro. nh hng ca lin kt hiro n tnh cht vt l.
GV chiu cc bi tp sau ln mn hnh cho HS tho lun. 1. C bao nhiu ancol c cng thc C3H8Ox. A. 3 C. 4 B. 5 D. Khng xc nh
p n B.
166

2. Sp xp cc cht sau theo th t tan tng dn:

CH3 CH2CH2OH (II). CH3CH2OH (I) , CH3CH2CH(OH)CH3(III), CH3OH(IV). A. (I) < (II) < (III < (IV). B. (II) < (III) < (I) < (IV). C.(IV)<(I)<(II)<(III). D.(III)<(II)<(I)<(IV)

p n D. 3. Xt ba cht: (I): CH3(CH2)3CH3; (II): CH3CH2CH(CH3)2; (III): C(CH3)4. Th t nhit si tng dn ca ba cht trn l: A. (I) < (II) < (III) B. (II) < (III) < (I) C. (III) < (II) < (I) D. (III) < (I) < (II) p n C 4. C bao nhiu ancol bc 2 c cng CTPT l C5H12O .

A. 2
5. ru l :

B. 3

C. 4

D. 5
p n B.

A. % khi lng ancol nguyn cht trong hn hp vi nc. B. % th tch ancol nguyn cht trong hn hp vi nc. C. % s mol ancol nguyn cht trong hn hp vi nc. D. Phn % khi lng ancol ho tan trong bt k dung mi no.
p n B. 2. Bi tp v nh 1, 2, 3, 4, 5, 6 (SGK) D. Hng dn gii bi tp SGK 1. V hnh thc th bc ca ancol bin i t 0 n III, nhng v thc cht th ngi ta ch chia ancol thnh 3 bc. 2. Gi tn:

a) CH3CH2CH2CH2OH b) CH3CH(OH)CH2CH3 c) (CH3)2COH

: ancol butylic ; : ancol sec-butylic;

butan-1-ol (bc 1) butan-1-ol (bc 2) 3-mentypropan-1-ol (bc 1) prop-2-en-1-ol (bc 1)

: ancol tert-butylic; 2-mentypropan-2-ol (bc 3)

d) (CH3)2CHCH2CH2OH : ancol isoamylic; e) CH2 = CHCH2OH : ancol anlylic;

167

CH2OH

g)
3. a) (CH3)2CHCH2OH;

: ancol benzylic

; phenylmetanol (bc 1)

b) (CH3)2CHCH2CH2OH
OH

c) CH3CHCH2CH2OHCH((CH3)2 e) CH2= CHCH2CH2OH; 1,344 4. n CO2 = = 0,006 (mol) 22,4

n H2 O =

d) g) C6H5 CH2CH2OH

1,62 = 0,009(mol) 18

Tnh tip ta c m c = 0,72g;

m H = 0,18g;

m o = 0,48g

CxHyOz ( x, y, z nguyn dng) 12x : y : 16z = 0,72 : 0,18 : 0,48 x:y:z=2:6:1 Cng thc n gin nht C2H6O suy ra (C2H6O)n MB = 23,2 = 46 (g/mol) n= 1 dB/H 2 = = 23 2 CH3CH2OH A ( ancol) CH3OCH2 B (ete).

5. CH3CH2CH2CH2 CH2OH: ancol pentylic (ancol amylic); pentan-1-ol

CH3CH2CH2 CH(OH) CH3: CH3CH2CH(OH) CH2CH3: (CH3)2 CHCH2 CH2OH: (CH3)2CHCH(OH) CH3: CH2(OH) CH(CH3) CH2 CH3: (CH3)3CCH2OH:

pentan-2-ol pentan-3-ol ancol isoamylic ; 3-metylbutan-1-ol 3-metylbutan-1-ol 2- metylbutan-2-ol ancol neopentylic ; 2,2-imetylbutan-1-ol

168

6. a) CH3OH c nhit si cao hn, tan tt hn trong nc hn CH3OCH3.

b) C2H5OH c nhit si cao hn, tan tt hn trong nc hn C2H5OCH3. c) C2H5F (ts = 380C); C2H5OH (ts = 78,30C). C2H5OH c nhit si cao hn, tan tt hn trong nc hn C2H5F. d) C6H5CH2OH c nhit si cao hn, tan tt hn trong nc hn C6H5OCH3. Gii thch: Ancol to c lin kt hiro lin phn t cn ete v C2H5F khng to c lin kt hiro lin phn t.

169

Bi 54

Ancol

Tnh cht ho hc, iu ch v ng dng

A. Mc tiu bi hc 1. Kin thc

HS bit:

Tnh cht ho hc c trng ca ancol v ng dng ca mt s ancol. Phng php iu ch ancol v ng dng ca etanol, metanol.
HS hiu:

Phn ng th H ca nhm OH, phn ng th nhm OH, phn ng tch nc v phn ng oxi ho.
2. K nng

Vit phng trnh ho hc ca phn ng th nguyn t H trong nhm OH v phn ng tch H2O theo quy tc Zai-xp. Vit phng trnh ho hc minh ho tnh cht ho hc ca ancol v glixerol. Gii c bi tp: phn bit ancol no n chc vi glixerol bng phng php ho hc, xc nh cng thc phn t, cng thc cu to ca ancol, mt s bi tp khc c ni dung lin quan. Bit cch quan st, phn tch v gii thch cc hin tng th nghim.
3. Tnh cm, thi

Bn cnh nhng li ch em li cn bit cch s dng hp l ancol trnh nguy him, t bo v trc nhng tc hi ca ancol.
B. chun b ca GV v HS

GV

My tnh, my chiu, cc phiu hc tp. Bng biu, phn mm. Ho cht: + Etanol. + Glixerol.

170

+ Dung dch Cu(OH)2. + Na kim loi .

+ Dung dch NaOH 10%. + Nc ct. + ng ht nh git.

Dng c:

+ ng nghim, my la.

+ Nt cao su c lp ng thu tinh vut nhn. + B gi th nghim .

HS: n tp kin thc v dn xut halogen v xem trc bi ancol.

C. tin trnh dy hc Hot ng ca GV Hot ng 1 Kim tra bi c Hot ng ca HS

GV gi 2 HS ln bng yu cu trnh HS ln bng trnh by. by cc ni dung sau: 1. Vit cng thc cu to thu gn cc HS 1 vit cc cng thc cu to: ancol c tn sau: pentan-2-ol CH3CH2CH2CH(OH)CH3 pentan-2-ol, ancol tert-butylic, ancol ancol tert-butylic (CH ) COH 3 3 benzylic, ancol anlylic. ancol benzylic C6H5CH2OH ancol anlylic CH2=CHCH2OH 2. Hon thnh s sau: HS 2 hon thnh s : CH4 A B etylbromua etanol
i. Tnh cht ho hc Hot ng 2

GV chiu hnh 8.2 ln mn hnh cho HS tho lun : HS quan st.

Lin kt OH phn cc mnh nn H yu cu HS phn tch c im cu trong nhm OH, d b thay th hoc tch ra trong phn ng ho hc. to t suy ra tnh cht ca ancol.

171

1. Phn ng th H ca nhm OH ancol Hot ng 3 a) Tnh cht chung ca ancol

GV lm th nghim :

HS quan st nhn xt:

Cho mu Na bng ht u xanh vo Hin tng v phng trnh ho hc: ng nghim kh cha 1-2 ml etanol Ban u c kh thot ra m du chng khan, gn thm ng thu tinh vut t c phn ng xy ra. nhn, t kh thot ra. Kh thot ra chy vi ngn la xanh nht, d on l kh H2: 2H2 + O2 2H2O Yu cu HS nu hin tng quan st 2C2H5OH + Na 2C2H5ONa + H2 c v d on kh thot ra. Gii natri etylat thch bng phng trnh ho hc? GV lm tip th nghim n khi Na tan ht, un nng ng nghim ancol etylic d bay hi ht. ngui ng nghim, rt 12 ml nc vo v cho mt t dung dch phenolphtalein vo. Yu cu HS nu hin tng quan st c. Gii thch bng phng trnh ho hc? GV hng dn HS gii thch hin tng v vit phng trnh ho hc chung ca ancol n chc vi Na: 2CnH2n+1OH + Na 2CnH2n+1ONa + H2 ancol

Khi un nng ng nghim thy ancol etylic bay hi li C2H5ONa bm vo thnh ng. Khi rt nc ct vo thy C2H5ONa tan, dung dch thu c lm phenolphtalin chuyn sang mu hng (chng t dung dch c tnh baz). Do c phn ng: C2H5ONa + H2O C2H5OH + NaOH

ancolat b) Tnh cht c trng ca glixerol

HS quan st. GV lm th nghim: Cho vo 2 ng nghim mi ng 3 4 git CuSO4 2% v 2 3 ml dung dch NaOH 10% lc nh. Yu cu HS quan st vit phng
172

trnh phn ng.

Hin tng thy kt ta xanh xut hin: CuSO4 + 2 NaOH Cu(OH)2 + Na2SO4
HS quan st v nhn xt:

Lm tip th nghim: cho vo mt ng 1: 3 4 git etanol, ng 2: 3 4 git glixerol, so snh hin tng xy ra 2 ng. Gii thch bng phng trnh phn ng.

ng (1) khng c hin tng. ng (2) thy Cu(OH)2 to thnh phc tan mu xanh da tri. Phng trnh ho hc: 2C3H5(OH)3 + Cu(OH)2 (C3H5(OH)2O)2Cu
+ 2H2O

GV nhn mnh: Phn ng ny dng nhn bit poliancol c cc nhm OH nh vi nhng nguyn t C cnh nhau. GV b sung cu to ca phc glixerol HS vit phng trnh ho hc: vi Cu(OH)2 HO CH2 CH2 OH CH2 OH HO CH2 CH OH + HO-Cu-OH + HO CH CH2 OH CH2 OH HO CH2 HO CH2 + 2H2O

CH O Cu O CH CH2 OH HO CH2

Yu cu HS vit phng trnh dng cu to thu gn.

CH O Cu O CH CH2 OH HO CH2

2. Phn ng th nhm OH Ancol Hot ng 4

GV lm th nghim: Cho ancol HS quan st th nghim v nhn xt: isoamylic vo 3 ng nghim A, B, C ng ln lt: nc ct, H2SO4 long v H2SO4 m c, lc k v yn.

173

yu cu HS:

Nu hin tng, gii thch.

Hin tng thu c:

ng nghim (A) ancol isoamylic hu nh khng tan trong nc. ng nghim (B) ancol isoamylic hu nh khng tan trong H2SO4 long. ng nghim (C) ancol iso amylic tan trong H2SO4 m c.

Gii thch: Ancol isoamylic hu nh khng tan trong nc, khng tc dng vi H2SO4 long nn khng tan, nhng tc dng c vi H2SO4 m c nn tan trong H2SO4 m c.

Vit phng trnh ho hc.

Phng trnh ho hc:

GV khi qut tnh cht ny: Ancol (CH3)2CHCH2CH2OH + H2SO4 tc dng vi cc axit mnh nh (CH3)2CHCH2CH2OS O3H + H2O H2SO4 m c lnh, HNO3 m isoamyl hirosunfat c, axit halogenhiric bc khi. Nhm OH b thay th bi gc axit. Phng trnh ho hc c dng: ROH + HX RX + H2O Yu cu HS vit phng trnh ho hc ca etanol vi HBr, glixerol vi HS vit phng trnh ho hc. HNO3. C2H5OH + HBr C2H5Br + H2O CH2 OH CH OH + 3HNO3 CH2 OH glixerol CH2 ONO2 CH ONO2 + 3H2O CH2 ONO2 glixerol trinitrat

174

3. Phn ng tch nc Hot ng 5 a) Tch nc lin phn t

GV m t th nghim, hng dn HS HS tho lun phn tch. phn tch th nghim: + cho 1 ml etanol khan vo ng nghim, nh t t 1 ml axit H2SO4 c lc u, un nh 1400C, sau cho t t tng git etanol dc theo thnh ng nghim vo hn hp ang nng thy c mi c trng ca ete etylic bay ra. Yu cu HS nu: Tc dng ca H2SO4 m c. Tc dng ca H2SO4 c: lm xc tc cho phn ng v ht nc Phng trnh ho hc. Ti sao ietyl ete d bay hi ? Cht bay ra l ete etylic nn phng trnh ho hc.
H 2 SO 4 C2H5OH+HOC2H5 C2H5OC2H5 + H2O o 140 C

V ietylete khng c lin kt hiro.

GV nhn mnh iu kin phn ng v nu ra bi tp: Nu un hn hp 2 ancol R1OH v R2OH ta c th thu c nhng ete no? Vit phng trnh ho hc. HS: C th thu c 3 ete: R1OR1, R1OR2, R2OR2.
H 2 SO 4 2R1OH R1OR1 + H2O o 140 C H 2 SO 4 2R2OH R2OR2 + H2O o 140 C H 2 SO 4 R1OR2 + H2O R1OH + R2OH o 140 C

b) Tch nc ni phn t

HS quan st tho lun: GV lm th nghim: Ly 1 ml ancol etylic sau cho t t 1 ml H2SO4 vo bnh cu c nhnh, un 1700C thy c kh bay ra, dn kh vo dung dch nc Br2. Yu cu HS: Hin tng c kh bay ra v kh lm Nu hin tng v gii thch? nc Br2 b nht mu.
175

HS: Gm etilen, etanol, SO2, CO2 v hi Hn hp kh bay ra khi un c th nc. gm nhng kh g? Nhng kh no c th lm mt mu Bng dung dch NaOH. nc Br2? HS: Gm bnh cu c nhnh gn vo gi, Loi CO2,SO2 bng cch no ? t trn n cn, nhnh dn kh i qua Vy b dng c th nghim c cu bnh 1 ng dung dch NaOH, kh thot to nh th no? yu cu HS m t ra t bnh NaOH dn vo bnh 2 ng dng c th nghim. Chng minh ch nc Br2. c etilen lm mt mu nc Br2. GV vit phng trnh ho hc minh HS: H 2 SO 4 ho v yu cu HS vit phng trnh C H Cn H2n + H2O o n 2n+1OH 170 C ho hc tng qut ca ancol: (tr metanol) H 2 SO 4 C2H5OH C2H4 + H2O o 170 C GV b sung: ancol tch nc theo HS ly v d. quy tc Zai-xep, yu cu HS cho v CH3CH CH CH2 d minh ho. H OH H GV nhn mnh iu kin phn ng CH3CH=CHCH3+ H2O tch nc ni phn t khc vi phn H2SO4 Sn phm chnh ng tch nc lin phn t. t0 CH3CH2CH=CH2+ H2O
Sn phm ph

4. Phn ng oxi ho Hot ng 6 a) Phn ng oxi ho khng hon ton

GV hng dn HS nghin cu SGK. Yu cu HS nhn xt: Cc trng hp oxi ho khng hon ton ca ancol. Sn phm ca mi trng hp. Vit phng trnh ho hc minh ho cho trng hp trn.

HS nghin cu SGK v nhn xt:

C ba trng hp ty vo cu trc ca ancol. + Nu oxi ho ancol bc I sn phm thu c l anehit.

t RCH=O + CuO+ H2O RCH2OH + CuO
o

176

 Mi trng hp cho mt v d.

t CH3OH + CuO HCH=O + CuO + H2O

o

+ Nu oxi ho ancol bc II sn phm thu c l xeton.

t RCHR+ CuO RCR+ CuO + H2O
o

OH

O
o

t H3CCH3 + CH3CHCH3+ CuO

OH

CuO+ H2O GV lu nguyn t H ca nhm OH v nguyn t H ca C gn vi nhm OH kt + Ancol bc III kh b oxi ho. Khi gp hp vi oxi ca CuO sinh ra nc. cht oxi ha mnh th b oxi ho lm gy mch cacbon.
b) Phn ng oxi ho hon ton

GV lm th nghim t chy ancol etylic cho HS quan st. Yu cu nhn xt: Hin tng. Vit phng trnh ho hc.

HS quan st v nhn xt: Ancol etylic chy mnh to nhiu nhit. Phng trnh ho hc
t 2CnH2n+1OH +3nO2 2nCO2 +2(n+1)H2O
o

t V d: C2H5OH + 3O2 2CO2 + 3H2O

o

T l s mol H2O v CO2. Nu ng dng ca phn ng chy.

t chy ancol no n chc mch h th n CO2 < n H2 O . ng dng lm nhin liu v st trng dng c y t.

II. iu ch v ng dng Hot ng 7 1. iu ch a) iu ch etanol trong cng nghip

GV yu cu HS lin h tnh cht ho HS lin h v nhn xt: hc ca anken. Nu tnh cht ho hc ca anken, Anken c phn ng cng H2, Br2 HX (X: tnh cht no c th dng iu ch Cl, Br, OH) ancol?
177

Vit phng trnh ho hc.

Phn ng cng hp vi H2O c th dng iu ch. Phng trnh ho hc

xt CnH2n + H2O CnH2n+1OH

xt v d: C2H4 + H2O C2H5OH

GV lin h cch nu ru trong dn gian. Yu cu HS nu: Cc bc iu ch ru trong dn gian. Trong cc bc trn bc no c cc qu trnh ha hc xy ra. GV cho HS bit thnh phn chnh ca go, ng, khoai, sn l tinh bt. Hng dn HS vit cc phng trnh ho hc. GV gii thiu: Ngy nay phng php ln men tinh bt c dng trong cng nghip sn xut etanol. Ngoi ra c th tng hp ancol bng cch thu phn dn xut halogen. Yu cu HS vit phng trnh ho hc.

HS tho lun v tr li.

Go, ng, khoai.. Nu chn men Nu ru. Bc c cc qu trnh ha hc xy ra

nu chn v men.
H C6H12O6 (C6H10O5)n + nH2O
+

enzim C6H12O6 2C2H5OH + 2CO2

HS vit phng trnh ho hc. RCl + NaOH ROH + NaCl

V d: C2H5Cl + NaOH C2H5OH + NaCl

b) iu ch metanol trong cng nghip

GV gii thiu: Trong cng nghip metanol c iu ch bng phng php oxi ho khng hon ton metan, yu cu HS vit phng trnh ho hc. Ngoi ra metanol cn c iu ch t cacbon oxit v kh hiro theo phng trnh ho hc sau:
ZnO,CrO3 CO + H2 CH3OH 400o C,200at

HS vit phng trnh ho hc. T metanol:

Cu 2CH3OH 2CH4 + O2 200o C,100at

HS lng nghe v ghi bi.

178

Hot ng 8 2. ng dng a) ng dng ca etanol GV su tm vt mu, tranh nh chiu HS quan st tng kt ng dng etanol: ln mn hnh cho HS quan st. Yu Cht u sn xut cc hp cht khc. cu HS nu cc ng dng c bn ca Dung mi. ancol etylic. Nhin liu cho ng c, n cn M phm, dc phm , phm nhum. iu ch cc loi ru ung. b) ng dng ca metanol GV cho HS nghin cu SGK v yu cu HS nghin cu SGK v nhn xt v ng nhn xt v ng dng c bn ca dng ca metanol ch yu dng : metanol. Sn xut anehit fomic, axit axetic. Phng trnh ho hc:
xt CH3OH + CuO HCHO + Cu +H2O xt CH3COOH CH3OH + CO

Tng hp mt s cht khc nh: metyl GV: Phn tch nhng li ch m amin, metyl clorua. etanol, metanol em li, cn bit tnh HS xem t liu(SGK). c hi ca chng i vi con ngi.
Hot ng 9 Cng c bi v bi tp v nh 1. Cng c bi GV nhc li cc ni dung cn nm vng cho HS:

Tnh cht ho hc c trng ca ancol v ng dng ca mt s ancol:

+ Phn ng th H ca nhm OH v th nhm OH ca ancol. + Phn ng tch nc, tch nc lin phn t. + Phn ng oxi ho ancol bc I cho anehit, ancol bc II cho xeton. + Phn ng ca glixerol vi Cu(OH)2. Phng php iu ch metanol v etanol.
179

GV chiu ln mn hnh cc bi tp sau HS tho lun. Cho s sau: 1.

AgNO3 / NH 3 CuO, t Ag C4H10O (X)
o

CTCT ph hp ca C4H10O l: A.CH3CH2CH2CH2OH. B.CH3CH2CH(OH)CH3.

2.

C.(CH3)3COH. D.(C2H5)2O.
p n A.

Sn phm chnh ca phn ng sau l cht no di y :

H 2 SO4 CH3CH(OH)CH(OH)CH3 t o >170o C

A. CH3CH(OH)CH=CH2. C. CH3COCH(OH)CH3.

B. CH2=CHCH=CH2. D. CH3CH=C(OH)CH3.
p n B.

3. Kh nc hon ton hn hp X gm 2 ancol A, B iu kin thch hp thu c hn hp Y gm 2 anken k tip nhau trong dy ng ng. Cho Y hp th ht vo bnh ng dung dch Br2 d thy c 24g Br2 b mt mu v khi lng bnh ng dung dch Br2 tng 7,35g. CTPT ca 2 ancol trong X l :

A. C2H5OH v C3H7OH. C. C3H7OH v C4H9OH.

4. Cho s chuyn ho sau:

B. C4H9OH v C5H11OH, D. Kt qu khc.

p n C

(A)

(B)

C2H5OH (E)

(C) (D)

Cc cht (A), (C), (D) c th l: A. C2H6; CH3CHO; CH3COOH B. C2H5Cl; CH3COOH; CH3COOC2H5 C. CH3COOC2H5; HCHO; HCOOH D. A hoc B
p n A 2. Bi tp v nh 1, 2, 3, 4, 5, 6, 7, 8, 9 (SGK)

180

D. Hng dn gii bi tp SGK 1. p n C.

H 2 SO 4 c,140 C 2. a) CH3CH(OH)CH3 (CH3)2CHOCH(CH3)2 + H2O lnh (CH3)2SO4 + 2H2O b) 2 CH3OH + H2 SO4 c
o

H2 SO4 c,t C c) CH3CH(OH)CH3 + HBr CH3CHBrCH3 + H2O

H 2 SO 4 c,180 C (CH3)2CHCH = CH2 + H2O d) (CH3)2CHCH2CH2OH
o

ancol isoamylic
o

3-metylbut-1-en

450 C 3. CH3CH = CH2 + Cl2 CH2ClCH = CH2 + HCl

CH2ClCH = CH2 + Cl2 + H2O CH2ClCHOHCH2Cl CH2ClCHOHCH2Cl + 2NaOH CH2OHCHOHCH2 + 2NaCl 4. Phng php ghp n s: Gi hai ancol ng ng k tip l: CnH2n+1 v CmH2m+1OH ; m = n + 1, n 1 1 CnH2n+1OH + Na CnH2n+1ONa + H2 (1) 2 1 CmH2m+1OH + Na CmH2m+1ONa + H2 (2) 2 Lp h phng trnh: (14n + 18)x + ( 14n + 32)y = 16,6 x + y = 0,3 y = 0,8 0,3n Bin lun: y>0 y < 0, 3 1,7 0,8 0,3n > 0 0,8 0,3n < 0 ,3 n 2,67

n< 2,67 n > 1,7

n=2

p n: C2H5OH v C3H7OH Tnh % khi lng: 46x + 60y = 16,6 x + y = 0,3 Gii h phng trnh, c: x = 0,1 hay 4,6 g C2H5OH
181

y = 0,2 hay 12g C3H7OH 4,6 % khi lng C2H5OH = . 100 = 27,71 % 16,6 % khi lng C3H7OH =
12 . 100 = 72,29% 16,6

Phng php trung bnh: Gi cng thc tng qut ca hai ancol l C n H 2 n +1 OH trong n l s nguyn t C trung bnh ca hai ancol. l khi lng mol phn t trung bnh ca hai ancol. 1 C n H 2 n +1 OH + Na C n H 2 n +1 ONa + H2 2 3,34 = 0,15 (mol) 0,3 mol 22,4

= 16,6 : 0.03 = 55,33 14 n + 18 = 55,33

n = 2,67 Vy hai ancol l: C5H5OH v C3H7OH 5. S iu ch CH3OH
Cl2 , as H 2 O , OH CH4 CH3Cl CH3OH Cl 2 , as CH3Cl + HCl CH4+ Cl2

t CH3Cl + NaOH CH3Cl + NaCl

o

a) Theo s trn th: + Lng ph giai on to ta CH3Cl v ho cht v thi gian. + Thi HCl c hi vo mi trng. CH4 + Cl2 to ra hn hp cc dn xut th nn sn phm km tinh khit. S HS ngh iu ch C2H5OH:
H 2 , Ni Cl2 , askt H 2 O , OH CH3CH3 CH3CH2Cl CH3CH2OH CH2=CH2 Ni CH2=CH2 + H2 CH3 CH3 o t

askt CH3CH2Cl + HCl CH3CH3 + Cl2

t CH3 CH2Cl + NaOH CH3 CH2OH + NaCl

o

S ny bt hp l ch: Bin etilen (l mt cht c kh nng phn ng cao, chn lc hn) thnh etan (l mt cht c kh nng phn ng thp, km chn lc hn), do tiu tn cc ho cht t tin nh: Cl2, NaOH, H2, nhiu

182

giai on, thi HCl c hi vo mi trng, giai on clo ho hnh thnh hn hp sn phm kh tch bit. b) S p dng trong cng nghip.
200 C,100atm,Cu 2CH3OH 2CH4 + O2
o

700 C,H3 PO4 CH2=CH2 + H2O CH3CH2OH

C hai s ch 1 giai on, s dng ho cht r tin ( O2, H2O) khng thi ra kh c.
6. a) Ly ng nghim mu ra mi ln ra mt t th c nhiu ln.

Ln lt cho tng cht (1), (2), (3) tc dng vi Cu(OH)2 th nhn ra cht (3) vi du hiu to ra phc duy nht mu xanh trong sut. Ln lt cho tng cht (1), (2) tc dng vi Na th nhn ra cht (2) vi du hiu kh H2 bay ra. Cn li l cht (1).
b) Ly mu cc ng nghim ra mi ln mt t th c nhiu ln .

Ln lt cho tng cht (1), (2), (3) tc dng vi Cu(OH)2 th nhn ra glixerol. Th hai cht cn li vi nc brom th nhn ra pen-4-en-1-ol. Cn li l xiclopentanol.
7. a) Cu to ca mentol, geraniol CH3

CH CH2 CH2 CH CH CH3 CH3 C CH2 CH2 CH C CH3 CH3 CH CH2OH CH3 CH2 CH-OH

Mentol l ancol no bc II. Tn theo IUPAC: 5- metyl-2-isopropylxiclohexan-1-ol

Geraniol l ancol khng no bc I tn theo IUPAC: 3,7-imetylocta-2,6-ien-1-ol

183

b) Phng trnh ho hc vi brom v vi CuO:

t0

+ CuO OH

+ H2O + Cu O

mentol (C10H20O) menton(C10H18O) mentol khng phn ng vi dung dch brom: CH2OH + CuO
t
0

CHO + H2O + Cu

Phn ng ca geraniol vi brom: Br CH2OH + 2Br2 Br Br

8. p n: nh hn. E. t liu tham kho 1. Ancol bc III bn vi cc cht oxi ho trong mi trng trung tnh v mi trng kim, trong mi trng axit b oxi ho ct mch cacbon thnh hn hp axit cacboxylic v xeton. V d: CH3CH2COOH + CH3CH2CCH3

Br

CH2OH

CH2CH3 CH3CCH2CH2CH3 + [O] OH

H+

O CH3COOH + CH3CCH2CH2CH3 O HCOOH + CH3CH2CCH2CH2CH3

O 2. Ngi ta thng phn bit nhanh ancol no cc bc da vo thuc th Lucas: hn hp HCl m c v ZnCl2 khan. Khi cho thuc th Lucas vo ancol cho ta dn xut clo tng ng, khng tan trong hn hp phn ng v tu theo hm lng, c th lm vn c dung dch hoc c hin tng tch lp:
184

ZnCl2 ZZZ X ROH + HCl YZZ Z RCl + H2O

Ancol bc III phn ng nhanh nhit phng, c hin tng tch lp. Ancol bc II phn ng chm sau khong 5 pht, c hin tng vn c. Ancol bc I hon ton khng phn ng nhit phng, to dung dch trong sut. 3. Mt s loi ancol c ngun gc t nhin c ng dng rng ri trong cng ngh nc hoa v trong thc phm. Mt s loi ancol l ngun nguyn liu ban u tng hp cht thm v nhng cht c hot tnh. V d. a) Hp cht bonbicol l mt loi ancol khng no c cu to: CH3(CH2)CH = CH CH = CH(CH2)8CH2OH Cht ny c tch ra t con ngi ci ca bm, tm v c tc dng dn d bm c thm ch khong cch rt xa. b) Geraniol v nerol l hai dng ng phn hnh hc ca nhau, chng c mi hoa hng, c tch t tinh du s, tinh du hoa hng. Geraniol l ng phn trans, cn nerol l ng phn cis, chng c cng thc cu to:
CH3 C CH2 CH2 CH C CH3 CH3 c) Linalol l ancol t nhin bc III, c tnh quang hot, c trong hu ht cc loi hoa thm v c cng thc cu to nh sau: OH CH3C= CHCH2CH2CCH=CH2 CH3 CH3 Linalol l ng phn cu to ca geraniol v nerol. CH CH2OH CH2OH

185

Bi 55
A. Mc tiu bi hc 1. Kin thc

Phenol

HS bit:

Khi nim, phn loi, cu to ca phenol. Tnh cht ho hc, mt s ng dng v phng php iu ch phenol.
HS hiu:

Tnh cht ho hc: Phn ng th nguyn t H ca nhm OH (tnh axit), phn ng th vng benzen, nh hng qua li gia cc nhm nguyn t trong phn t phenol. Mt s phng php iu ch hin nay, ng dng ca phenol. Khi nim v nh hng qua li gia cc nguyn t trong phn t hp cht hu c.
2. K nng

Phn bit phenol v ancol thm bng phng php ho hc Vn dng tnh cht ho hc gii ng bi tp. Vit cc phng trnh ho hc minh ho tc dng ca phenol vi natri hiroxit, dung dch brom.
3. Tnh cm, thi

Xt mi quan h tnh cht ca phenol gip HS hiu thm v mi quan h bin chng trong khoa hc, t to hng th trong hc tp cho HS.
B. chun b ca GV v HS

GV:

My tnh, my chiu. Ho cht: + Phenol.

+ Dung dch phenol. + Nc ct.

+ Nc brom. + Na kim loi. + ng ht nh git.

Dng c :
186

+ ng nghim.

+ Nt cao su c lp ng thu tinh vut nhn. + B gi th nghim.

HS: n tp bi ancol v xem trc bi phenol.

C. tin trnh dy hc Hot ng ca GV Hot ng 1 Kim tra bi c Hot ng ca HS

GV gi 2 HS ln bng trnh by cc ni dung sau: 1. Ba ancol A, B, C mch h khng phi l ng phn ca nhau. t chy mi cht u sinh ra CO2 v H2O theo t l mol n CO2 : n H2 O = 3 : 4. Tm cng thc phn t ca mi cht.

HS1 trnh by bi gii: Cng thc phn t ancol A: CxHyOz Khi t A CxHyOa xCO2 + y/2 H2O Ta c x : y = 3 : 8. Cng thc A l (C3H8Oa)k tng t ta c CTPT ca B, C l (C3H8Ob)k v (C3H8Oc)k cc ancol u no, mch h c dng CnH2n+2Ok, k 3 v chng khng phi l ng phn ca nhau, nn chng thuc cc dy ng ng khc nhau. C th l C3H8O, C3H8O2, C3H8O3

2. Ancol no n chc mch h X to HS 2: c ete Y. T khi hi ca Y so vi X gn bng 1,61. Tn ca X l A. metanol B. etanol C. propan-1-ol D. propan-2-ol p n B. GV nhn xt bi lm ca hai HS cho cc HS rt kinh nghim.
I. nh ngha, Phn loi v tnh cht vt l Hot ng 2 1. nh ngha

GV chiu cng thc 2 cht sau ln mn

187

hnh:

OH

CH2OH

(1) (2) Yu cu HS nhn xt v cu to phn HS tho lun v nhn xt: t ca 2 cht trn? + u c vng benzen. + u c nhm OH. Khc nhau: + Cht th nht nhm OH gn trc tip vi vng benzen. + Cht th hai nhm OH gn gin tip vo nhn benzen thng qua 1 nhm CH2. GV b sung: Bit cht th nht l phenol cht th hai l ancol thm yu cu HS: Rt ra nh ngha phenol? Nu mt s v d: nh ngha: Phenol l nhng hp cht hu c trong phn t c nhm OH lin kt trc tip vi nguyn t C ca vng benzen. Ancol thm:
CH2CH2OH CH2OH

Phenol:

OH

OH

CH3

Hot ng 3 2. Phn loi

GV cho HS nghin cu SGK v yu HS nghin cu SGK v nhn xt: cu nu c s phn loi phenol, cho v Da vo s nhm OH trong phn t, d minh ho? phenol c phn thnh 2 loi: Phenol n chc (phn t c 1 nhm OH). V d:

188

OH

OH

OH

CH3

phenol 3-metylphenol -naphtol Phenol a chc (c nhiu nhm OH)

OH OH OH OH CH3

hiroquinon
Hot ng 4 3. Tnh cht vt l

3,4-ihiroxi toluen

GV cho HS quan st ng nghim ng mt t phenol, sau un nng nh. Yu cu HS nu cc tnh cht vt l quan st c. GV lm th nghim ho tan phenol trong nc lnh, nc nng v etanol lc nh. GV b sung cho HS: Phenol tan v hn 660C. Trong qu trnh bo qun phenol thng b chy ra v thm mu do ht m v b oxi ho bi oxi khng kh. Phenol rt c, khi tip xc n c th gy bng da nn phi cn thn khi s dng. GV so snh t0s ca etanol v phenol, t d on kh nng to lin kt hiro lin phn t ca C6H5OH.

HS quan st v nu hin tng qnan st c:

Phenol l cht rn, khng mu, d nng chy khi un nh. Phenol t tan trong nc, tan nhiu trong nc nng v etanol.

HS nhn xt: Phenol c nhit si cao hn etanol l do phenol c lin kt hiro bn hn ancol (v do khi lng phn t ln). O HO H C 6H 5 C 6H 5

189

II. Tnh cht ho hc Hot ng 5 1. Tnh axit

GV lm th nghim: Ly 2 ng nghim HS quan st v nu hin tng: mi ng cha 1 t phenol.

ng nghim 1 thm 2ml nc ct. ng nghim 2 thm 2ml NaOH c.

ng nghim1 mu phenol khng tan. ng nghim 2 mu phenol tan ht.

Lc u c hai ng, yu cu HS quan Nhn xt: st v gii thch ?

Phenol hu nh khng tan trong nc lnh. Phenol tan tt trong dung dch NaOH.
(1) (2)

Gii thch v c phn ng:

C6H5ONa + NaOH C6H5ONa + H2O GV lm tip th nghim sc CO2 vo HS khi sc kh CO2 vo ng nghim 2 ng nghim 2 yu cu HS: (dung dch natriphenolat) thy dung Quan st hin tng gii thch. dch b vn c. Do phenol tch ra theo Nhn xt tnh axit ca phenol. phn ng: C6H5ONa+ CO2+ H2O C6H5OH +NaHCO3 Qua phn ng trn nhn thy + Tnh axit ca phenol mnh hn ancol (tc dng c vi dung dch NaOH) GV b sung: Dung dch phenol khng + Tnh axit ca phenol rt yu (b axit lm i mu giy qu tm. cacbonic y ra khi mui phenolat) GV: Tng t ancol, phenol phn ng HS vit phng trnh ho hc. vi kim loi kim v yu cu HS vit 2C6H5OH + 2Na 2C6H5ONa + H2 phn ng ho hc v gi tn sn phm? natri phenolat

190

Hot ng 6 2. Phn ng th vng thm

GV phn tch cu to phenol, kh nng HS lng nghe. th ca phenol so vi benzen. Mt electron vng benzen tng ln lm giu electron ti C v tr ortho v para. So vi benzen th phenol d th hn v u tin th v tr ortho, para. chng minh kh nng th, GV lm th nghim: Cho benzen, dung dch HS quan st v nhn xt: phenol vo 2 ng nghim. Sau nh t t dung dch Br2 vo lc nh, yu cu HS quan st v nhn xt: Nu hin tng. ng nghim cha phenol c kt ta trng xut hin. Phn ng th vo nhn thm Mc phn ng so vi benzen. phenol d hn benzen (iu kin m du hn, th ng thi c 3 v nguyn t H v tr ortho v para).

Gii thch. Phng trnh ho hc minh ho.

l do nh hng ca nhm OH n vng benzen. Phng trnh ho hc

OH + 3Br2 Br OH Br + 3HBr trng

Br 2,4,6-tribromphenol GV: tng t yu cu HS vit phn ng HS vit phng trnh ho hc: ca phenol vi HNO3 c c H2SO4 c xc tc.

191

GV b sung: phn ng vi dung dch brom dng nhn bit phenol.

OH O 2N +3HNO3
H2SO4 c

OH NO2 + 3H2O vng

NO2 2,4,6-trinitrophenol
Hot ng 7 3. nh hng qua li gia cc nhm nguyn t trong phn t phenol

GV chiu m hnh 8.5 ln mn hnh cho HS quan st, tho lun v nhn xt .. HS quan st. O H

Yu cu HS nhn xt v: Cu to ca phenol so vi benzen. So vi benzen: Mt eletron trn cc nguyn t + C hai u c nhn thm (H lin kt cacbon v oxi. lin hp khp kn). + Phenol c nhm OH phn cc. Oxi cn c cp e t do b vng benzen ht gy ra hiu ng y electron vo vng benzen lm giu e cc v tr ortho v para v lm ngho trn nguyn t oxi (lm phn cc lin kt OH).

D on cc tnh cht ho hc c th HS phn tch: c ca phenol ? C nhm OH ging ancol nn phenol c kh nng th H ca nhm OH. Phenol c nhn thm, nn c phn ng th halogen tng t benzen. GV: t nhng tnh cht ho hc hc, HS rt ra kt lun: yu cu HS kt lun tnh cht ho hc. nh hng ca nhm OH n vng
benzen v nh ca vng benzen n nhm OH l nh hng qua li gia cc nguyn t trong phn t.

192

III. iu ch v ng dng Hot ng 8 1. iu ch

GV gii thiu: Trong cng nghip hin HS: tho lun v vit phng trnh ho nay phenol c iu ch bng phn hc. ng oxi ho cumen (Isopropylbenzen) nh oxi khng kh. Sn phm thu c gm phenol v axeton. un nng axeton bay hi cn li phenol. GV chiu ln mn hnh s sau, yu cu HS vit phng trnh ho hc: OH CH3CHCH3 T benzen: CH3CHCH3
+ + CH2=CHCH3 H

CH3CHCH3

OH + CH3CCH3

+ O2

O GV: C th iu phenol theo cch no HS: Thu phn dn xut halogen. ? Vit s iu ch t benzen ? Br ONa

OH

GV b sung iu kin cc phn ng HS vit phng trnh ho hc: gip HS hon thnh s . C6H6 + Br2 C6H5Br + HBr o GV gii thiu: Ngoi ra 1 lng phenol C H Br + NaOH t NaBr + C6H5ONa 6 5 p ng k c thu bng cch tch ra C6H5ONa + HCl C6H5OH + NaCl trong nha than .
Hot ng 9 2. ng dng

GV su tp tranh nh, mu vt chiu HS quan st, nghin cu SGK.

193

 Sn xut poli phenolfomanehit. ln cho HS quan st. GV yu cu HS nhn xt ng dng ca iu ch dc phm, phm nhum, thuc n, cht kch thch sinh trng phenol. thc vt, cht tr su b GV b sung: Bn cnh ch li em li Nhn xt: Phenol l nguyn liu quan th phenol gy c hi vi con ngi v trng trong cng nghip ho cht. mi trng.
Hot ng 10 Cng c bi v bi tp v nh 1. Cng c bi

GV nhc li cc ni dung cn nm vng cho HS: Mi quan h gia cu trc v tnh cht ca phenol. Cch gi tn ca cc phenol

Tnh cht ho hc c trng ca phenol:

+ Phn ng th H ca nhm OH. + Phn ng th cc v tr ortho v para (th Br2, HNO3). Phng php iu ch phenol trong cng nghip. GV chiu ln mn hnh cc bi tp sau HS tho lun. 1. Trong cc pht biu sau : 1) C2H5OH v C6H5OH u phn ng d dng vi CH3COOH. 2) C2H5OH c tnh axit yu hn C6H5OH. 3) C2H5ONa v C6H5ONa phn ng hon ton vi nc cho ra C2H5OH v C6H5OH. Chn pht biu sai : A. Ch c (1). B. Ch c (2). C. (1) v (2). D. (1) v (3).

p n D. 2. C bao nhiu ng phn ng vi cng thc phn t C8H10O, bit cc ng phn u c vng benzen v u phn ng c vi dung dch NaOH . A. 6 B. 7 C. 8 D. 9 p n D.
194

3. C bao nhiu loi lin kt hiro trong hn hp lng ru etylic v phenol?

D. khng c lin kt hiro. p n C. 4. Cho 3 hp cht hu c sau: (1) C2H5OH, (2) C6H5OH, (3) p-O2NC6H4OH. Khng nh no sau y khng ng? A. C 3 cht u c hiro linh ng. B. C 3 cht u phn ng c vi baz iu kin thng. C. Cht (3) c hiro linh ng nht. D. Th t linh ng ca hiro sp xp theo chiu tng dn (1) < (2) < (3).
p n B. 5. Tnh axit ca hp cht no sau y yu nht?

A. 5.

B. 3.

C. 4.

A. Axit picric. C. p- nitrophenol.

B. Phenol. D. p- crezol

p n D. 6. Phn ng brom ho phenol vi lng d Br2/H2O c th thu c sn phm chnh l cht no di y? A. Monobrom phenol. B. ibrom phenol. C. Tribrom phenol. D.2,4,4,6-tetrabrom xiclohexaienon. p n D. 2. Bi tp v nh 1, 2, 3, 4, 5, 6 (SGK) D. hng dn gii bi tp SGK

a) S. b) . c) S. 1. 2. Cng thc cu to ca cc cht l: CH2OH OCH3 OH CH3

d) S. OH CH3 OH

CH3 p-crezol
(5)

ancol benzylic metyl phenyl ete

(1) (2) (3)

o-crezol

m-crezol
(4)

Cht (1) l ancol; cht (2) ete; cht (3), (4) , (5) l phenol

195

3. a) C6H5OH + NaOH C6H5ONa + H2O

C2H5OH khng tc dng vi NaOH Gii thch: C 2H 5 O H

.. O

Lin kt OH phenol phn cc mnh hn etanol. Do vy phenol c kh nng tch thnh ion H+ d dng hn so vi C2H5OH. b) .. O H O N O

4.

Do hiu ng trn m mt electron vng benzen ca phenol cao hn mt electron vng benzen ca nitrobenzen. Phn ng th vo vng benzen do cc tiu phn tch in dng tn cng. Do vy mt electron cao hn th phn ng th d hn. OH OH + 3H2 Tch da vo tnh cht vt l v ho hc Ho tan hn hp hai cht vo dung dch NaOH c chuyn C6H5OH thnh C6H5ONa tan trong nc. Xiclohexanol rt t tan trong nc nn c chit khi dung dch C6H5ONa. Trong dung dch cn C6H5ONa, sc CO2 d vo chit ly phenol.
Ni

t0

C6H5ONa + CO2 + H2O C6H5OH + NaHCO3 5. a) OH C2H5OH Nc brom Kt ta trng Tan hon ton Tan t, phn thnh lp ni ln trn OH

196

b) OH CH2OH CH OH CH2OH glixerol Dung dch mu xanh C AgCl OH + 3HBr (trng) Br 0,04 mol CHCH2 Br Br (2) Br (1) CH2Cl

p-crezolCH3 Cu(OH)2 dd AgNO3

6. Phng trnh ho hc: OH

benzyl clorua

+ 3Br2 Br 0, 04 mol 0,04 mol 3

CH=CH2 + Br2 0,02 mol HBr + NaOH 0,02 mol NaBr + H2O

(3) 1,11.14,4.10 S mol NaOH tham gia phn ng (3) l : 0,04 (mol) 133.40 300,0.3,2 S mol Br2 tham gia phn ng (1) v (2) l : = 0,06 (mol) 100.160 a s liu ln lt vo phng trnh ho hc tnh, ta c kt qu : 94.0,04 mphenol = = 1,253 (g) mstiren = 104 x 0,02 = 2,08 (g) 3 Phn trm v khi lng ca mi cht trong hn hp ban u: 1,253.100% 2,08.100% Phenol: = 37,59% Stiren: = 62,41% 3,333 3,333
E. t liu tham kho

Phenol c tnh axit mnh hn so vi ancol nhng li yu hn so vi axit cacboxylic, V d: pKa (CH3OH) = 16, pKa(CH3COOH) = 4,8 v pKa (phenol) = 10.
197

.. O

- + H+ O

pKa = 10

S d tnh axit ca phenol ln hn ancol l do nh hng ca vng benzen nn phn cc ca lin kt OH trong phenol ln hn trong ancol. Mt khc n nh ca anion phenolat bn hn so vi anion ancolat. Cc nhm th c hiu ng I v C trong vng thm s lm tng tnh axit ca phenol. Ngc li cc nhm c hiu ng +I, +C s lm gim tnh axit. Ngoi ra, cc nhm th v tr khc nhau s gy nh hng n tnh axit khc nhau. S ph thuc ca tnh axit vo v tr cc nhm th ca phenol. pKa (250C) Nhm th ompH CH3 Cl CH3O CN NO2 10,00 10,29 8,49 9,98 7,17 10,00 10,09 9,02 9,65 8,28 10,00 10,26 9,38 10,21 7,95 7,15

198

Bi 56

luyn tp ancol, phenol

A. Mc tiu bi hc 1. Kin thc

Cng c h thng ho tnh cht ho hc v phng php iu ch ancol, phenol, lm cho HS hiu: Mi lin quan gia cu trc v tnh cht c trng ca ancol, phenol. S ging nhau v khc nhau v tnh cht ho hc gia ancol v phenol.
2. K nng

Rn luyn k nng so snh, tm mi lin h gia thc c bn lp bng tng kt, t c cch nh h thng. Vn dng kin thc hc, t bit cch gii ng bi tp.
3. Thi , tnh cm thc cn thn, trung thc, kin tr, chnh xc trong hc tp ho hc. B. chun b ca GV v HS

GV: HS:

My tnh, my chiu, h thng cc cu hi v bi tp n tp. n tp kin thc cc bi ancol v phenol. Chun b trc ni dung luyn tp nh.

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I. Kin thc cn nm vng Hot ng 1

GV nu cc vn c bn hc:
199

 Cu trc ca phenol, ancol. Tnh cht ho hc ca phenol, ancol. iu ch v ng dng phenol, ancol.
Chiu bng tng kt kin thc, trng cc thng tin. Yu cu HS a ra cc th d minh ho HS tho lun v in vo bng. phn tch v khc su v cng c kin thc hc.
Bng tng kt kin thc

Ancol
1. Cng thc 2. Cu trc
+

Phenol C6H5OH

CnH2n+1OH

.. O
+

4. Tnh cht ho hc

a) Th nhm OH b) Th H ca nhm OH c) Tch H 2O d) Th vng benzen. e) Phn ng oxi ho khng hon ton

CnH2n+1OH+HBrCnH2n+1Br +H2O CnH2n+1OHCnH2n+1OCnH2n+1 H2O 2ROH +2 Na 2RONa + H2

C6H5OH+HX Khng xy ra 2C6H5OH+2Na2C6H5ONa + H2

H2 SO 4 c CnH2n+1OH o CnH2n + H2O 170 C

C6H5OH + 3 Br2 (C6H5OH)Br3+ HBr ancol bcI + CuO anehit + Cu + H2O ancol bcII + CuO xeton + Cu+ H2O

200

5. iu ch Cng H2O vo anken.

Th X ca dn xut halogen. iu ch etanol t tinh bt.

6. ng dng

Th H ca benzen sau thu phn dn xut halogen bng NaOH c. Oxi ho Cumen.

Nguyn liu sn xut anehit, Dng sn xut cht do, axit, este, cht do, dung mi, thuc n, dc phm, phm nhin liu, ung, dc phm. nhum, thuc tr dch hi.

Hot ng 2 II. Bi tp GV chiu bi tp 1 (SGK) ln mn hnh HS tho lun. 1. Hy in ch (ng) hoc S (sai ) vo du [ ] mi cu sau:

a) Ancol l hp cht nhm OH lin kt trc tip vi nguyn t C lai ho sp3 .[ ] b) Phenol l hp cht cha OH lin kt trc tip vi nguyn t C lai ho sp2.[ ] c) Phn t ancol khng cha vng benzen. [ ] d) Lin kt C O ancol bn hn lin kt C O phenol. [ ] e) Lin kt C O ancol phn cc hn lin kt C O phenol. [ ] HS tho lun v a ra kt qu: a) []. V nguyn t cacbon no l nguyn t cacbon lai ho sp3. b) [S]. V anken cng c Csp3 hai nguyn t C mang lin kt i. c) [S]. V ancol thm cng c vng benzen. d) [S]. V lin kt C O ancol km bn hn. e) [S]. V lin kt O H km phn cc hn. GV chiu bi tp 3 (SGK) ln mn hnh HS tho lun. 3. Hon thnh cc phng trnh ho hc ca phn ng sau, v r rng vng benzen: a) o-BrC6H4CH2Br + NaOH (dd) ; b) p-HOCH2C6H4OH + HBr c) m- HOCH2C6H4OH + NaOH (dd) ; d) p- CH3C6H4OH + Br2 (dd) HS tho lun v a ra kt qu: CH2Br Br a) + NaOH(dd) CH2OH Br

to

NaBr

201

CH2OH
b)

CH2Br + HBr CH3 CH2OH + NaOH(dd) CH3 Br OH Br ONa + 2HBr + H 2O + H 2O

CH3 CH2OH
c)

CH3
d)

OH + 2Br2(dd)

OH

GV chiu bi tp 4 (SGK) ln mn hnh HS tho lun. 4. Hin nay trong cng nghip ngi ta iu ch etanol v phenol nh th no ? Vit s phn ng. HS tho lun v a ra kt qu: iu ch etanol:
men (C6H10O5)n + nH2O nC6H12O6
l n men r u 2C2H5OH + 2CO2 C6H12O6

H 3 PO 4 C2H5OH hoc CH2 =CH2 + H2O

iu ch phenol:
CH 2 = CH CH3 1) O2 ;2) H 2 SO 4 C6H6 C6H5CH (CH3)2 C6H5OH + CH3COCH3 H3 PO4

GV chiu bi tp 5 (SGK) ln mn hnh HS tho lun. 5. t chy hon ton mt hn hp vi hai ancol k tip nhau trong dy ng ng ca metanol, ngi ta thu c 3,584 lt CO2 (ktc) v 3,96 g H2O. a) Xc nh cng thc phn t ca hai ancol v thnh phn trm ca chng trong hn hp. b) Hai ancol ny c th c cng thc cu to nh th no? HS tho lun v a ra kt qu: Cch 1: C n H 2n +1 OH +

3n O2 n CO2 + ( n + 1) H2O 2

x mol

n x mol

( n + 1) x mol

202

n X=

3,96 3,584 = 0,16 ( n + 1) x = = 0,22 22,4 18 0,16 = 2,67 0,06

x = 0,06 suy ra n =

v 2 ancol k tip nhau nn n < 2,67 < n + 1, vy n = 2 2 C2H5OH 2,67 3 C3H7OH

C2H5OH v C3H7OH. Cch 2: CnH2n+1OH nCO2 +(n +1) H2O x Cn+1H2n+3OH nx ( n + 1) x (n+1)CO2 + (n+2) H2O

y (n+1)y (n+2)y n(x + y) + y = 0,16 n(x + y) + x + 2y = 0,22 (x + y ) = 0,66 0,16 y n= 0, 06 0 < y < 0,06 1,67 < n < 2,67

n = 2 C2H5OH v C3H7OH GV chiu bi tp 6 (SGK) ln mn hnh HS tho lun. 6. Hy vit phng trnh ho hc ca phn ng thc hin cc chuyn ho sau: a) CH3CH2CH2Br thnh CH3CHBrCH3 b) (CH3)2CHCH2CH2OH thnh (CH3)2C(OH)CH2CH3 HS tho lun v a ra kt qu:
C 3 H 7 OH, t 6. a) CH3CH2 CH2Br CH3CH = CH2 + KBr + H2O o

CH3CH = CH2 + HBr CH3CHBr CH3

H2 SO4 ,t b) (CH3)2CHCH2CH2OH (CH3)2CHCH =CH2 + H2O H (CH3)2CHCH =CH2 + H2O (CH3)2CHCHOHCH3
+

H2 SO4 ,t (CH3)2CHCHOHCH3 (CH3)2C=CHCH3 + H2O H (CH3)2C= CHCH3 + H2O (CH3)2COHCH2CH3

+

GV chiu bi tp 7 (SGK) ln mn hnh HS tho lun.

203

7. Hon chnh s phn ng sau (cc ch ci ch sn phm chnh):

CH3CHCH2CH2Cl KOH, oetanol A

t

HCl

B KOH, etanol C
t to NaOH
o

HCl

D
to NaOH H2O

CH3

NaOH
H2O

to HOH H+

H2O

to HOH H+

E G HS tho lun v a ra kt qu: Phng trnh ho hc:

o

KOH,e tan ol,t (CH3)2CHCH2 CH2Cl (CH3)2CHCH = CH2 HCl

(A) (B) (C) (D) (E) (H) (K) (G) (I)

(CH3)2CHCH = CH2 + HCl (CH3)2CHCHClCH3

KOH,e tan ol,t (CH3)2CHCHClCH3 (CH3)2C= CHCH3 HCl
o

(CH3)2C =CHCH3 + HCl (CH3)2CClCH2CH3 (CH3)2CH CH2CH2Cl (CH3)2CHCH2ClCH3

+ NaOH (CH3)2CHCH2CH2OH
+ NaOH (CH3)2CHCHOHCH3

+ NaOH (CH3)2CClCH2CH3 (CH3)2COHCH2CH3

H (CH3)2CHCH= CH2 + H2O (CH3)2C(OH)CH2CH3 o t H (CH3)2C = CH CH3 + H2O (CH3)2C(OH)CH2CH3 o t
+

Bi tp ngh 1. Cht 3-MCPD (3-monoclopropan-1,2-iol) thng ln trong nc tng v c th gy ra bnh ung th. Cht ny c cng thc cu to l: A. CH2CHCH2 B. CH2CHCH2

OH Cl OH C. CH3CHCHOH Cl OH

OH OH Cl D. OH CH2C CH2Cl OH

p n B. 2. Hiro ho cht A c cng thc C4H6O c ancol butylic. S cng thc cu to ca A l: A. 3 B. 4 C. 5 D. 6 p n B.

204

3. Cho cc cht p-crezol (1), m-crezol (2), o-crezol (3)

Tnh axit tng dn theo dy: A. (1) < (2) < (3). C. (3) < (1) < (2).

B. (3) < (2) < (1). D. (2) <(1) < (3).

p n C. 4. Hn hp X gm 2 ancol A, B c cng s nhm chc OH. Chia X thnh 2 phn bng nhau:

Phn 1: Cho tc dng vi Na d thu c 2,24(l) H2 (ktc). Phn 2: t chy hon ton thu c 11(g) CO2 v 6,3(g) H2O. Bit s nguyn t cacbon trong ancol 3. Cng thc phn t ca A, B l: C. CH3OH v C2H5OH . A. C2H5OH ; C3H7OH. B. C2H4(OH)2 v C3H7(OH)2. D. CH3OH v C3H7OH.
p n B. 5. Theo IUPAC hp cht (CH3)2C=CHCH2OH c tn gi l:

A. 3-metylbut-2-en-1-ol C. Pent-2-en-1-ol

B. 2-metylbut-2-en-4-ol D. Ancol isopent-2-en-1-ylic

p n A. 6. Chiu gim linh ng ca nguyn t H trong nhm OH ca 3 hp cht gm C6H5OH, C2H5OH v H2O l :

A. H2O, C6H5OH,C2H5OH C. C2H5OH ,C6H5OH, H2O

B. C6H5OH, H2O v C2H5OH D. C2H5OH , H2O, C6H5OH

p n B. 7. un ancol A no, n chc vi H2SO4 c thu c hp cht hu c B c dB/A = 0,7. Xc nh cng thc phn t ca A? A. C3H5OH. B. C3H7OH. D. C4H9OH. C. C4H7OH. p n B. 8. Cho cc cht sau :Phenol (1), p-nitrophenol(2),p-crezol(3), p-aminophenol(4)

Tnh axit tng dn theo dy: A. (3) < (4) < (1) < (2). B. (4) < (1) < (3) < (2).

C. (4)<(3)<(1)<(2). D. (4)<(1)<(2)<(3).
p n C.

205

Bi 57

thc hnh

tnh cht ca mt vi dn xut halogen, ancol v phenol

A. Mc tiu bi hc 1. Kin thc

Cng c kin thc v tnh cht vt l v ho hc ca mt s dn xut halogen, ancol, phenol. Bit c mc ch, cch tin hnh, k thut thc hin cc th nghim c th: Thu phn 1,2-icloetan hoc mt s dn xut monoclo. Glixerol tc dng vi Cu(OH)2. Phenol tc dng vi nc brom. Phn bit ba dung dch mt nhn: etanol, glixerol v phenol
2. K nng

S dng dng c, ho cht tin hnh c an ton, thnh cng cc th nghim trn. Chn thuc th thch hp phn bit c mi dung dch. Quan st, m t hin tng, gii thch v vit cc phng trnh ho hc. Tip tc rn luyn k nng tin hnh th nghim vi lng nh ho cht.
3. Tnh cm, thi

Thng qua hot ng thc hnh lm tng s hng th hc tp ca HS i vi b mn ho hc.

B. chun b ca GV v HS

GV

My tnh, my chiu, cc phiu hc tp.

1. Ho cht: + Etanol. + Glixerol.

206

+ Dung dch CuSO4 + Dung dch NaOH 10% + Na kim loi. + Nc ct. + Nc brom. + Phenol. + HCl. + 1,2-icloetan hoc clorofom. + Dung dch AgNO3. + HNO3. 2. Dng c: + ng nghim , n cn. + ng ht nh git. + Gi ng nghim. + B gi th nghim.

HS:

n tp tnh cht ca etanol, glixerol v phenol. Xem trc bi thc hnh.

C. tin trnh dy hc Hot ng ca GV Hot ng 1 Dn d trc bui thc hnh Hot ng ca HS

GV nu cc ni dung chnh ca bui HS nghe GV trnh by v tho lun theo nhm thc hnh. thc hnh. GV yu cu HS trnh by cc ni dung kin thc lin quan n bui thc hnh. Lu HS khi dng ho cht v s dng cn thn cc dng c th nghim. Chia lp hc thnh cc nhm thc hnh, mi nhm gm 57 HS.
I. Ni dung th nghim v cch tin hnh Hot ng 2 Th nghim 1. Thu phn dn xut halogen GV yu cu HS tin hnh th nghim HS tin hnh th nghim. nh SGK. Thm 2ml nc ct vo ng nghim cha 0,5ml 1,2-icloetan hoc clorofom
207

GV yu cu HS m t hin tng.

GV hng dn HS gii thch. Cu trc ca 1,2 icloetan.

Kh nng phn ng vi NaOH. Ti sao phi axit ho dung dch? C kt ta chng minh iu g?

( ra sch Cl bng nc ct). Cho tip 1ml dung dch NaOH 20% vo ng nghim. un si gn ly lp nc axit ho bng HNO3 ri th bng dung dch AgNO3. HS quan st v nhn xt: Trong ng nghim xut hin kt ta trng. HS tho lun v gii thch: 1,2-icloetan c lin kt CCl phn cc c th b thu phn bi NaOH khi un nng to ra etan-1,2-iol. Phi axit ho dung dch trnh Ag+ kt ta dng AgOH. C kt ta chng minh 1,2-icloetan b thu phn to ra Cl. Phng trnh ho hc:
t C2H4Cl2 + 2OH C2H4(OH)2 + 2Cl
o

Ag+ + Cl
Hot ng 3

AgCl

Th nghim 2. tc dng ca glixerol vi Cu(OH)2 GV yu cu HS chun b cc ho cht HS nghin cu ti liu, chun b ho CuSO4 10%, NaOH 10%, glixerol, cht. etanol. Tin hnh th nghim: GV hng dn HS tin hnh th Cho vo hai ng nghim mi ng mt nghim nh SGK v yu cu HS quan t dung dch Cu(OH)2 5% v thm vo st v gii thch hin tng qua cc mi ng 2ml dung dch NaOH 10% lc giai on. nh, yn vi pht. Cho tip vo ng nghim th nht 5 git glixerol, ng nghim th hai 5 git etanol ri lc nh c hai ng nghim. Quan st thy hin tng:
208

 Giai on 1:
Khi cho NaOH vo ng nghim ng dung dch CuSO4 th thy mu xanh ca dung dch nht dn. ng thi thy xut hin kt ta xanh. CuSO4 + NaOH Cu(OH)2 + NaSO4 Giai on 2: Cho glixerol vo bnh c cha Cu(OH)2 thy kt ta tan. ng thi xut hin dung dch mu xanh lam do Cu(OH)2 to phc vi glixerol, ng nghim cha etanol khng c hin tng g. Gii thch: Do glixerol phn ng vi Cu(OH)2 to ra phc c mu xanh c trng. GV gii thiu phn ng to phc: HO CH2 CH2 OH CH OH + HO-Cu-OH + HO CH CH2 OH CH2 OH HO CH2 HO CH 2 CH O Cu O CH + 2H2O

CH2 OH HO CH2 Phc ng(II) glixerat c mu xanh lam. GV yu cu HS nh t t HCl vo hai HS tip tc tin hnh th nghim. ng nghim v quan st hin tng xy Nh t t HCl vo hai ng nghim. ra. Lc nh c hai ng nghim. Hin tng: GV b sung: Etanol khng phn ng vi ng nghim th nht xut hin dung dung dch HCl. dch c mu xanh nht ca CuCl2.

ng nghim th hai thy kt ta Cu(OH)2 tan nhanh v xut hin dung dch mu xanh nh ng nghim th nht.

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Hot ng 4 Th nghim 3. Phenol tc dng vi nc Br2

GV yu cu HS chun b dung dch Br2 v dung dch phenol. Nhc nh HS cn thn khi lm vic vi phenol v phenol lm bng da v dng dung dch bo ho phenol nhit phng. Nu hin tng quan st c, gii thch.

HS tin hnh th nghim.

HS: Thy c kt ta trng xut hin, do c phn ng gia phenol v brom to ra 2,4,6-tribromphenol. Phng trnh ho hc: OH + 3Br2 Br Br OH Br + 3HBr

(trng)
Hot ng 5 Th nghim 4: Phn bit Etanol, Phenol v Glixerol GV hng dn HS phn tch cc th HS tho lun v a ra s phn bit nghim trn yu cu HS xut s etanol, phenol v glixerol. c th nhn bit 3 cht trn. etanol, phenol v glixerol
+ nc Br2

khng c hin tng kt ta xut hin etanol, glixerol + Cu(OH)2 khng c hin tng kt ta tan phenol

etanol glixerol GV chiu s ln mn hnh yu cu HS: Tin hnh th nghim v nhn xt: HS tin hnh th nghim, kim tra xem C th dng s trn nhn bit c th nhn bit c 3 cht bng s c 3 cht. trn c hay khng?
210

GV nu ra mt cu hi sau: C th lp mt s khc nhn bit cc cht HS tho lun v nhn xt: C th i ch trn c khng. giai on 1 bng Cu(OH)2, giai on 2 bng nc Br2.
Hot ng 6 II. Cng vic sau bui thc hnh

GV nhn xt v bui thc hnh v HS thu dn, v sinh phng th nghim hng dn HS thu dn ho cht, ra cn thn, an ton. ng nghim v dng c th nghim, v sinh phng th nghim. GV yu cu HS lm tng trnh theo HS lm tng trnh theo mu sau y: mu: Ngy thng.nm. H v tn: Lp:. T th nghim:. Tng trnh ho hc bi s:. Tn bi:
Tn th nghim Phng php tin hnh Hin tng quan st Gii thch vit phng trnh phn ng

211

Chng IX Anehit - xeton Axit cacboxylic

Bi 58

anehit v xeton

A. Mc tiu bi hc 1. Kin thc

HS bit:

nh ngha anehit v xeton, c im, cu trc phn t, phn loi, danh php. Tnh cht vt l anehit v xeton. Phng php iu ch anehit t ancol bc I, iu ch trc tip anehit fomic t metan, anehit axetic t etilen. Mt s ng dng chnh ca fomaehit, axetanehit, axeton.
HS hiu:

Tnh cht ho hc c trng ca anehit: phn ng cng, phn ng oxi ho, phn ng gc hirocacbon. Xeton c phn ng cng vi hiro, phn ng gc hirocacbon. Cc phng php sn xut mi.
2. K nng

D on c tnh cht ho hc c trng ca anehit v xeton, kim tra d on v kt lun. Quan st th nghim, hnh nh, rt ra c nhn xt v cu to v tnh cht. Vit c cc phng trnh ho hc minh ho tnh cht ca anehit, xeton. Gii c bi tp: phn bit anehit v xeton bng phng php ho hc, tnh khi lng hoc nng anehit tham gia phn ng.

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3. Tnh cm, thi

Thng qua vic nghin cu cc anehit, xeton, HS cm nhn c mt cch t nhin cc mi quan h bin chng gia cu to v tnh cht, nh hng qua li gia cc nguyn t trong phn t, gip HS t xc nh c cch sng tt trong x hi. Mi cht anehit, xeton u c tnh ch li v tnh c hi ca n i vi con ngi v mi trng sng, thng qua vic hc cc cht ny, HS thy r phi c kin thc v chng s dng chng phc v con ngi mt cch an ton.

B. chun b ca GV v HS
GV: My tnh, my chiu.
Ho cht: Dng c: + Dung dch fomanehit. + Dung dch AgNO3 1%. + ng nghim. + n cn. + Xeton. + Dung dch NH3 10%. + ng ht nh git.

HS: n tp kin thc bi ancol v xem trc bi anehit-xeton.

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

i. nh ngha, cu trc, phn loi, danh php v tnh cht vt l Hot ng 1 1. nh ngha v cu trc a) nh ngha

GV chiu cng thc phn t mt s anehit, HS quan st v tho lun: xeton ln mn hnh cho HS quan st: HCH=O, CH3CH=O, C6H5CH=O CH3COCH3 O=CH CH=O, CH3 COC6H5

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Yu cu HS nhn xt: c im chung v cu to.

HS nhn xt: c im chung u c nhm cacbonyl. C O Da vo cu to c th chia cc cht Da vo cu to c th chia cc trn thnh bao nhiu nhm. cht trn thnh hai nhm. nhm 1 gm : HCH=O, CH3CH=O, C6H5CH=O, O=CHCH=O. nhm 2 gm: CH3 CC6H5 CH3 C CH3 O O GV cho bit nhm 1 l anehit v nhm HS tho lun v a ra nh ngha. 2 l xeton, yu cu HS nu nh ngha + Anehit l hp cht hu c m anehit, xeton. phn t c nhm CH=O lin kt trc tip vi nguyn t C (nguyn t C y c th l gc hirocacbon hoc C ca nhm CHO khc) hoc nguyn t H. + Xeton l nhng hp cht hu c m phn t c nhm CO lin kt trc tip vi 2 nguyn t C.
b) Cu trc ca nhm cacbonyl

GV chiu cu trc ca nhm cacbonyl (a) HS quan st v nhn xt: m hnh phn t anehit fomic (b) v xeton (c) ln mn hnh cho HS quan st:

Yu cu HS nhn xt v:

214

 Trng thi lai ho ca C mang ni i. C lin kt i trng thi lai ho sp2. Cu to ca nhm cacbonyl. Nhm cacboyl >C=O c cu to gm: Mt lin kt bn v mt lin kt km bn, gc gia cc lin kt nhm >C=O xp x 1200. So snh cu to ca nhm cacbonyl So vi lin kt C=C th c hai u c lin kt , gc lin kt gn bng vi lin kt C=C. nhau v nguyn t C trng thi lai ho sp2 nhng trong nhm cacbonyl cc lin kt b phn cc mnh (nguyn t O mt phn mang in tch m, nguyn t C mang mt phn in tch dng) cn trong >C=C< th hu nh khng phn cc.
Hot ng 2 2. Phn loi

GV cho HS nghin cu SGK v yu cu HS nghin cu SGK v nhn xt: HS nu:

C s phn loi anehit, xeton.

Da vo c im cu to ca anehit.

Cu to gc hirocacbon hoc s Cch phn loi theo cu to gc nhm cacbonyl. hidrocacbon cho v d minh ho. Theo cu to gc hirocacbon th anehit v xeton c chia lm ba loi: + No: CH3CHO, C2H5CHO, CH3COCH3, CH3CH2COCH3 + Khng no: CH2=CHCHO, CH3CH=CHCHO, CH2=CHCOCH3
215

+ Thm: C6H5CHO, CH3C6H4CHO C6H5COCH3, C6H5COC6H5 HS phn loi: + Anehit n chc: GV yu cu HS phn loi anehit theo CH3CHO, C6H5CHO. s lng nhm CHO. + Anehit a chc: (CHO)2, CH2(CHO)2 HS thit lp cng thc tng qut: GV: Tng t ancol, lp cng thc tng CxH2x+1CHO ( x 0) qut ca anehit no n chc mch h. vit gn CnH2nO (n 1)
Hot ng 3 3. Danh php

GV yu cu HS nghin cu SGK t HS nghin cu SGK v tr li: rt ra cch gi tn thay th anehit cu Tn thay th c cu to: to mch h. Tn hirocacbon tng ng al Cch chn mch chnh. vi mch chnh Cch nh s. Mch chnh ca phn t anehit l

Cch gi tn.
GV ly v d: CH3 CH CH CHO 3-metylbutanal CH3 GV yu cu HS gi tn cc anehit c cng thc phn t C5H10O.

mch C di nht c cha nhm CHO.

nh s th t bt u t nhm CHO.

HS vit cc ng phn v gi tn. CH3CH2CH2CH2CHO pentanal CH3CH2CHCHO 2-metylbutanal CH3 CH3CHCH2CHO 3-metylbutanal CH3
216

CH3 GV: Nu cch gi tn thng thng v CH3CCHO 2,2-imetylpropanal cho HS luyn cch gi tn cc anehit CH3 trong bng 9.2 SGK HS: Tn thng thng ca cc GV nu tn mt s anehit khc: CH2=CHCHO CHO CHO GV tip tc yu cu HS nu cch gi HS nu cch gi tn xeton: tn ca xeton. Tn thay th ca xeton c cu to: Tn hirocacbon tng ng vi mch chnh S ch v tr C ca nhm >C on = OCO V d: CH3COCH3 propan-2-on CH3COCH=CH2 but-3-en-2-on Tn gc-chc c cu to: Tn gc hirocacbon xeton V d: imetyl xeton CH3COCH3 CH3COCH=CH2 metyl vinyl xeton CH3COC6H5 metyl phenyl xeton
Hot ng 4 4. Tnh cht vt l GV yu cu HS nghin cu SGK v HS nghin cu SGK. nhn xt v: Trng thi ca anehit, xeton. HCHO l cht kh, CH3CHO l Mu sc, mi. cht lng, cc anehit khc l cht

anehit acrylic

anehit n gin c ngun gc lch s nh: CH3COOH axit axetic CH3CHO anehit axetic (axetanehit)

C6H5CHO anehitbenzoic (benzaehit) anehit oxalic (etanial)

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 tan. Nhit nng chy, nhit si.

lng hoc rn, axeton l cht lng. Anehit v xeton thng khng c mu, nhng li c mi ring v d:

HCHO c mi xc, xitral c mi s, axeton c mi thm nh, menton c mi bc h. Ch mt s anehit, xeton n gin tan c trong nc v tan gim dn. Anehit v xeton c nhit nng chy, nhit si cao hn so vi hirocacbon tng ng nhng thp hn ancol c cng s nguyn t C. GV yu cu HS gii thch ti sao HS gii thch anehit v xeton c anehit v xeton c nhit nng chy, khi lng phn t ln hn nhit si khc vi hirocacbon v hirocacbon c cng s nguyn t C nhng do khng c lin kt hiro nn ancol c cng s nguyn t C. nhit nng chy, nhit si thp hn ancol. V d: GV b sung: CH3CHO (nhit si l 210C). HCHO tan tt trong nc cho dung dch C2H5OH (nhit si l 78,30C). HCHO (37 40%) c gi l fomalin Axeton tan v hn trong nc.
II. Tnh cht ho hc Hot ng 5 1. Phn ng cng a) Phn ng cng hiro (phn ng kh)

GV gii thiu cho HS bit anehit v xeton c ni i C=O ging anken, yu cu HS d on tnh cht ca anehit v xeton, tng t anken vit phng trnh phn ng gia anehit vi H2.

HS phn tch v nhn xt: Ging anken, anehit v xeton c phn ng cng hiro(c xc tc v un nng). Phng trnh ho hc:
Ni RCH=O + H2 RCH2OH to

218

Ni CH3 CH=O + H2 CH3CH2OH to Ni R C R + H2 R CH R to

O OH Ni CH3COCH3+H2 CH3CHCH3 to OH + Trong cc phn ng trn anehit v HS anehit v xeton ng vai tr l xeton ng vai tr nh th no v sn cht oxi ho. phm l g ? Anehit cng H2 sn phm l ancol bc I. Xeton cng H2 sn phm l ancol bc II. b) Phn ng cng nc, cng hiro xianua GV hng dn HS vit phn ng cng HS vit phng trnh ho hc. ca fomanehit vi nc GV b sung: Sn phm cng khng bn H2C=O + HOH U H2COH tch ra khi dung dch nc. OH (khng bn) GV cho HS nghin cu SGK v yu cu HS nghin cu SGK v nhn xt: HS nhn xt v: C ch phn ng (gii thch). C ch phn ng xy ra qua hai giai on: Sn phm to thnh. + Giai on 1: CN tn cng C=O . Vit phng trnh ho hc. + Giai on 2: ion H+ tn cng sau. Gii thch: do C trong lin kt C=O mang in tch dng nn CN d tn cng vo C ny trc. Sn phm to thnh bn gi l xianohirin. Phng trnh ho hc: CH3CH=O + NC CH3CHO C N

GV hng dn HS vit phng trnh ho CH3CHO + H+ CH3CHOH hc minh ho (GV c th vit mu cho HS C N C N

219

phn ng ca anehit vi HCN, ri cho HS OH t vit phn ng ca xeton vi HCN ). CH3COCH3+HCN CH3CCH3
Hot ng 6 2. Phn ng oxi ho a) Tc dng vi brom v kali pemanganat

C N

GV lm th nghim so snh:

HS quan st nhn xt.

Nh nc Br2 vo dung dch axetanehit. Nh nc Br2 vo dung dch axeton. Nh dung dch kalipemanganat vo dung dch axetanehit. Nh dung dch kalipemanganat vo Hin tng: dung dch axeton. Dung dch axetanehit lm nht Yu cu HS nu hin tng. mu dung dch brom v kalipemanganat. Dung dch axeton khng lm nht mu dung dch brom v dung dch kali pemanganat.
HS gii thch:

GV t vn : Ti sao c s khc nhau Xeton kh b oxi ho cn anehit d v yu cu HS gii thch (GV hng dn b oxi ha, n lm nht mu dung dch brom v dung dch HS gii thch). kalipemanganat. GV b sung:

Anehit b oxi ho thnh axit HS vit phng trnh ho hc: cacboxylic (RCOOH), yu cu HS vit RCHO + Br2 + H2O RCOOH + 2HBr KMnO 4 phng trnh ho hc. RCHO + [O] RCOOH Xeton kh b oxi ho, khi b oxi ho gy mch C nhm cacbonyl to thnh hn hp axit theo phng trnh ho hc

220

CH3CH2COCH3 + O2 HCOOH + CH3CH2COOH CH3CH2COCH3 + O2 2CH3COOH b) Tc dng vi ion bc trong dung dch amoniac GV trnh by th nghim: Cho vo ng nghim 1 ml dung dch AgNO3 sau thm dn tng git dung dch amoniac lc u n khi dung dch trong sut th dng li, sau thm tip CH3CHO un nng nh vi pht. HS quan st thy:

+ Ban u khi cho dung dch NH3 vo Yu cu quan st hin tng v gii dung dch AgNO thy dung dch b 3 thch bng phng trnh ho hc . vn c v: AgNO3+NH3 + H2O AgOH +NH4NO3

Sau thm tip NH3 dung dch li trong sut tr li v:

AgOH+2NH3[Ag(NH3)2]+OH(tan)

Khi thm CH3CHO un nh thy bc kim loi bm vo thnh ng nghim.

CH3CHO + 2AgNO3 + 3NH3 + H2O to CH3COONH4+2Ag+ 2NH4NO3

GV: Vit phng trnh tng qut cho HS vit phng trnh ho hc tng anehit no n chc. GV: Trong phn ng cht no l cht qut.
t oxi ho, cht no l cht kh, ch ra s RCHO + 2AgNO3 + 3NH3+H2O thay i s oxi ho ca cc nguyn t. RCOONH4 + 2Ag + 2NH4NO3
o

HS: Ion Ag+ l cht oxi ho Ag+ Ag0 RCHO l cht kh C+1 C+3 GV yu cu HS nu ng dng ca phn HS trng gng soi, trng rut phch. ng ny m em bit.

Dng nhn bit anehit.

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GV b sung: Ngoi phn ng trn anehit cn c mt s phn ng vi cht oxi ho khc nh:
t RCHO + 2Cu(OH)2 + NaOH
o

RCOONa + Cu2O + 3H2O

Hot ng 7 3. Phn ng gc hirocacbon

GV gii thiu: Nhng nguyn t H ca HS lng nghe. C cnh nhm cacbonyl d tham gia Phng trnh ho hc: phn ng th bi nguyn t halogen do CH 3 COOH CH3COCH3 +Br2 c tnh linh ng. Yu cu HS vit CH3COCH2Br + HBr phng trnh ho hc minh ho.
III. iu ch v ng dng Hot ng 8 1. iu ch a) T ancol

T tnh cht ho hc ca ancol GV yu HS nhn xt: cu HS nu phn ng c th dng Oxi ho ancol bc 1 thu c anehit iu ch anehit, xeton. Vit phng RCH OH + CuORCHO+ H O + Cu 2 2 trnh ho hc minh ho. to CH3CH2OH + CuO CH3CHO + H2O + Cu Oxi ho ancol bc 1 thu c anehit. V d:
t CH3CCH3+Cu CH3CHCH3+CuO O + H2O OH
o

GV b sung: HCHO trong cng nghip HS vit phng trnh ho hc. c iu ch bng cch oxi ho CH OH + O t o ,Cu HCHO + H2O 3 2 metanol nh oxi khng kh 600 7000C vi xc tc l Cu hoc Ag, yu cu HS vit phng trnh ho hc.
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b) T hirocacbon

GV yu cu HS nghin cu SGK, yu cu nhn xt: Nguyn liu dng iu ch anehit, xeton trong cng nghip Vit cc phng trnh ho hc.

HS nhn xt: trong cng nghip c cc phn ng iu ch t hidrocacbon nh: a. T metan:

t xl HCHO + H2O CH4 + O2
0

b. T etilen:
PdCl2 ,CuCl2 ,t 2CH2=CH2+O2 2CH3CHO 0

c. T axetilen:
HgSO 4 CH CH + H2O CH2=CHOH

CH3CHO

Khng bn

d. T cumen(oxi ho cumen): GV b sung: Trong cng nghip anehit OH CH3CHCH3 c iu ch t axetilen t c dng v gi thnh cao. + O2 + CH3CCH3 O phenol axeton
Hot ng 9 2. ng dng

GV: Su tm vt mu, tranh nh chiu ln mn hnh cho HS quan st v yu cu HS nu cc ng dng c bn ca fomanehit, axetanehit, axeton.

HS quan st v nhn xt cc ng dng c bn ca anehit-xeton. Fomanehit c dng sn xut poli fomanehit, dung dch HCHO khong 37 40% c gi l fomon c dng ngm xc ng vt, thuc da, ty u, dit trng. Axetanehit dng ch yu sn xut axit axetic. Axeton c dng lm dung mi (l dung mi rt ph bin) trong sn xut nhiu loi ho cht cng nh polime. Axeton cn c dng tng hp nhiu loi ho cht khc nh clorofom, ioofom, bisphenol-A,
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Hot ng 10 Cng c bi v bi tp v nh 1. Cng c bi

GV khc su mt s kin thc cho HS v:

Cu trc, phn loi v danh php ca anehit v xeton. Nhit si ca anehit v xeton thp hn ancol tng ng. Phn ng cng H2, phn ng trng bc ca anehit v phn ng oxi ho ca xeton. Phng php sn xut mi v ng dng ca anehit v xeton.
GV chiu cc bi tp sau ln mn hnh HS tho lun.
1. Gi tn hp cht c CTCT sau theo danh php IUPAC:

C2H5 CH3 CH CH2 CH CHO C2 H 5 A. 2,4- ietylpentanal. B. 2-metyl-4-etylhexanal. C. 2-etyl-4-metylhexanal. D. 2-metyl-5-oxoheptan.

p n D. 2. t chy hon ton mt hp cht hu c X thu c CO2 v H2O ( n CO2 = n H2 O ).

X thuc nhm hp cht no sau y: A. Anken hay ancol khng no c 1 ni i trong phn t. B. Anehit no n chc hoc xeton no n chc. C. Axitcacboxylic no n chc hoc este no n chc. D. C A, B, C.
p n D. 3. t chy mt hn hp ng ng anehit ta thu c n CO2 = n H2 O th l

dy ng ng ca A. Anehit n chc no. C. Anehit hai chc no. B. Anehit vng no. D. C A, B, C u ng.
p n A.
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4. Cht no sau y khng phn ng c vi dung dch AgNO3/ NH3?

A. CH3 C CH. C. HCl.

B. CH3CHO. D. (CH3)2CO.

p n C. 5. Cho 4,2 gam anehit mch h phn ng ht vi Ag2O, trong dung dch NH3 d. Ton b lng bc thu c ho tan ht trong HNO3 c, nng nhn c 3,792 lt NO2 270C v 740 mmHg. Bit t khi hi ca X so vi nit nh hn 4 (cho H=1, C=12, N=14, O=16, Ag=108). Cng thc cu to ca X l: B. CH2=CHCHO. A. CH CCHO. D. CH2=CHCH2CHO. C. CH3CH2CHO. p n B. 6. iu kin no thc hin chuyn ho sau:

CH2 = CH C CH CH2 = CH CO CH3 A. H2O/ Hg2+(H+). C. H2O/ OH. B. H2O/ H+. D. H2O/ KMnO4
p n A. 2. Bi tp v nh: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 (SGK) D. Hng dn gii bi tp SGK 1. Lin kt C=O gm lin kt v lin kt . C v O u trng thi lai ho sp2, c m in ln hn nn ht electron v pha mnh lm cho lin kt tr thnh phn cc. O mang in tch , C mang in tch +. 2. CnH2n+1CHO vi n 0; CnH2n+1COCmH2m+1 vi n 1 v m 1

(Ch : Cng thc chung phi c nhm chc). 3. a) CH3CHO axetanehit; etanal b) CH3CHClCHO 2-clopropnal 2-metylpropanal c) (CH3)2CHCHO acrylanehit; prop-2-en-l-al d) CH2=CHCHO e) transCH3CH= CHCHO trans-but-2-en-l-al g) CH3COC2H5 h) p- CH3C6H4CHO i) Cl3CCHO k) CH2=CHCOCH3 etyl metyl xeton; butan-2-on p-metylbenzanehit cloran; 2,2,2tricloetanal metyl vinyl xeton; but-3-en-2-on
225

4. Vit cng thc cu to ca cc hp cht sau:

a) Fomanehit b) Benzanehit c) Axeton d) 2-Metylbutanal e) But-2-en-1-al g) Axetophenon

HCHO C6H5CHO CH3COCH3 CH3 CH2CH(CH3)CHO CH3CH=CHCHO CH3 COC6H5

h) Etyl vinyl xeton C2H5COCH =CH2 i) 3-Phenylprop-2-en-1-al C6H5 CH= CHCHO 5. a) Cng thc phn t CnH2nO c th thuc nhng loi hp cht no? Cho th d i vi C3 H6O. Anehit hoc xeton: CH3CH2CHO, CH3COCH3 Ancol khng no: CH2= CHCH2OH Ancol v ete vng no: CH2 CH CH3 CHOH CH2 CH2 CH2CH2 CH2 O O

b) Vit cng thc cu to cc hp cht cacbonyl ng phn c cng thc phn t C5H10O. Anehit: 1) CH3CH2CH2CHO 2) CH3CH2CH(CH3)CHO

Xeton:

3) CH3CH(CH3)CH2CHO 1) CH3CH2CH2COCH3

4) (CH3)3CCHO 2) (CH3)2CHCOCH3

3) CH3CH2COCH2CH3. 6. Hy gii thch v sao: a) Propan-2-ol (ts = 820C) CH3CH(OH)CH3 to lin kt hiro lin phn t mnh nn nhit si cao. Propanal (ts = 490C) CH3CH2CHO khng to lin kt hiro lin phn t nhng c lin kt phn cc mnh. (C= O) nn c nhit si trung bnh. 2-metylpropen (ts= 70C) (CH3)2C=CH2 khng to lin kt hiro lin phn t, khng phn cc, nn c nhit si thp . b) Anehit fomic HCHO (M=30 g/mol) tan trong nc tt hn so vi etan C2H6 (M=30 g/mol) v c kh nng to lin kt hiro vi nc (xem bi 56 SGK).
226

Ni,t 7. a) RCHO + H2 RCH2OH

o

Ni,t R'COR" + H2 R'CH(OH)R"

o

b) Anehit d b oxi ho cn xeton kh b oxi ho. RCHO + 2[Ag(NH3)2]OH RCOONH4 + 2Ag + 3NH3 + H2O R'COR" khng c phn ng trng bc. Anehit tc dng vi nc brom, dung dch thuc tm nhit phng, xeton khng b oxi ho trong iu kin trn. c) Fomanehit + H2O sn phm khng bn, khng tch c H2C = O + H2O
8. a) S;

H2C OH OH c) ; d) S; e) S

b) S;
xt t o ,p

9. a) CO + 2H2 CH3OH

CH3OH +

1 Cu,t o O2 HCHO + H2O 2

HCHO + 2AgNO3 + 3NH3 + H2O HCOONH4 + 2NH4NO3 + 2Ag ( tip tc tham gia phn ng trng bc)
1 PdCl2 ,CuCl2 O2 CH3CHO to 2 CH3CHO + HCN CH3CH(OH)CN

b) CH2 = CH2 +

H ,t c) C6H5CH =CH2 + H2O C6H5CH(OH)CH3

o

t C6H5CH(OH)CH3 + CuO C6H5COCH3 + H2O + Cu

o

H C6H5COCH3 + Br2 C6H5COCH2Br + HBr

Ni,t d) C6H5OH + 3H2 C6H11OH O OH

o

+ CuO O

t
o

+ Cu + H2O O Br + HBr

H + Br2

227

10. nCuO =

7,95 32,4 = 0,1 (mol) ; nAg = = 0,3 (mol) 108 80 V ancol n chc nn ta c tng s mol hai ancol = tng s mol CuO = na tng s mol Ag hay tng s mol Ag = 2 ln s mol CuO . Nhng s liu cho tng s mol Ag = 3 ln s mol CuO, suy ra trong hn hp c CH3CH to ra HCHO phn ng cho lng Ag gp i cc anehit n chc khc. Vy hn hp c CH3OH v RCH2OH vi s mol bng nhau l: 0,1 : 2 = 0,05 (mol)
t CH3OH + CuO HCHO + Cu + H2O
o

t RCH2OH + CuO RCHO + Cu + H2O

o

HCHO + 4AgNO3 + 6NH3 + 2H2O 4NH4NO3 + (NH4)2 CO3 + 4 Ag RCHO + 2AgNO3 + 3NH3 + H2O 2NH4NO3 +RCOO NH4 + 2Ag 32. 0,05 + (R+ 31). 0,05 = 4,60 R l C2H5 Hn hp 2 ancol gm: CH3OH v C3H7OH.

228

Bi 59

luyn tp Anehit v xeton

A. Mc tiu bi hc 1. Kin thc

Thng qua vic h thng ho kin thc v luyn tp lm cho HS: Nm vng s ging nhau v khc nhau v cu trc v tnh cht ho hc ca
anehit v xeton.

Bit cc ng dng thng thng ca anehit v xeton. Vn dng gii bi tp nhn bit, so snh.
2. K nng

Rn luyn k nng so snh, tm mi lin h gia kin thc c bn lp

bng tng kt, t c cch nh h thng.

Vn dng kin thc hc t bit cch gii ng bi tp.

3. Tnh cm, thi

Gip HS nhn thc c cc cht hu c gn gi vi i sng v nhng hiu bit v chng l rt cn thit, gip chng ta s dng hp l, c hiu qu cc sn phm ho hc, t tng dn lng yu thch b mn.
B. chun b ca gv v hs.

GV: HS:

My tnh, my chiu, h thng cc cu hi v bi tp n tp. n tp bi cc bi anehit-xeton v axit cacboxylic. Chun b trc ni dung luyn tp nh.

229

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I. Kin thc cn nm vng Hot ng 1

GV nu cc vn c bn hc:

Khi nim anehit, xeton. c im cu trc lin kt nhm cacbonyl. Tnh cht ho hc c bn ca anehit, xeton. Phng php iu ch v ng dng ca anehit, xeton.
GV: Chia HS theo cc nhm (4 nhm) v chiu bng di y ln mn hnh cho HS quan st v giao ni dung luyn tp cho cc nhm.

HS lng nghe v chun b cc ni dung luyn tp.

Bng tng kt kin thc v anehitxeton

Anehit Cu trc Lin kt hiro Tnh cht vt l Tnh cht ho hc iu ch

ng dng

Xeton

GV t chc hng dn HS tho lun cc ni dung trn in cc thng tin vo bng.

230

GV yu cu HS (nhm 1) nu cu trc HS (nhm 1) tho lun v nhn xt: v xt kh nng to lin kt hiro vi Cu trc ca anehit v xeton. nc ca anehit, xeton. R R + + C = O C=O R H anehit xeton Nhn xt: c anehit, xeton u c nhm cacbonyl C=O. C lin kt ging anken nhng lin kt i trong anken khng b phn cc.

dng nguyn cht c anehit v xeton u khng c lin kt hiro, nhng trong dung dch c kh nng to lin kt hiro vi nc nh sau:
H C R R C R O H O H O H O H

GV yu cu HS (nhm 2) nu tnh HS (nhm 2) tho lun v nhn xt: cht vt l ca anehit v xeton. iu kin thng anehit C1 v C2 l cht kh, cc anehit khc l cht lng hoc rn c nhit si cao hn hirocacbon nhng thp hn ancol tng ng. Anehit C1 v C2 tan tt trong nc. Cc anehit u c mi ring.

iu kin thng cc xeton l cht lng hoc rn c nhit si cao hn hirocacbon nhng thp hn ancol tng ng. Khi s C trong phn t tng th tan trong nc gim dn. GV yu cu HS (nhm 3) nu tnh HS (nhm 3) tho lun v nhn xt:
231

cht ho hc ca anehit v xeton.

u c phn ng cng hiro

Ni RCH=O + H2 RCH2OH to Ni CH3COCH3 + H2 CH3CHCH3 to u c phn ng cng HCNOH

CH3CH=O + HCN CH3CHOH C N C N OH CH3COCH3 + HCN CH3CCH3 C N Ring anehit c phn ng trng gng, lm mt mu dung dch brom, KMnO4 RCHO + Br2 + H2O RCOOH + 2HBr RCHO + 2AgNO3 + 3NH3+H2O RCOONH4 + 2Ag + 2NH4NO3 Nhn xt: anehit d b oxi ho hn xeton. GV yu cu HS (nhm 4) nu phng HS (nhm 4) tho lun v nhn xt: php iu ch v ng dng ca Anehit c iu ch t ancol bc I, anehit v xeton. xeton c iu ch t ancol bc II. Ngoi ra anehit cn c iu ch t:
t ,xt HCHO + H2O CH4 + O2
0

t ,xt 2CH2 = CH2 + O2 2CH3CHO

0

Xeton c iu ch t cumen: CH3CHCH3 + O2 OH

+ CH3CCH3 O Fomanehit c dng sn xut poli fomanehit, dung dch HCHO khong 3740% gi l fomon c dng ngm xc ng vt, thuc da, ty u, dit trng. Axetanehit dng ch yu sn xut axit axetic. Axeton c dng lm dung mi (l
232

dung mi rt ph bin) trong sn xut nhiu loi ho cht cng nh polime, mt s xeton khc c dng sn xut nc hoa. GV nhn xt kt qu ca mi nhm, b sung v chiu bng tng kt y (bng SGK) cho HS h thng kin thc.
Hot ng 2 II. Bi tp

GV chiu bi tp 1 (SGK) ln mn hnh HS tho lun. 1. Hy nu c im cu trc ca nhm cacbonyl, v nhn xt v s khc nhau gia nhm chc anehit v nhm chc xeton. HS tho lun v a ra kt qu: Cu trc ca nhm cacbonyl (>C=O): nguyn t C mang lin kt i trng thi lai ho sp2. Lin kt C=O gm mt lin kt bn v mt lin kt km bn. Nhm cacbonyl trong phn t xeton c cu trc tng t nhm cacbonyl trong phn t anehit. Tuy nhin nguyn t cacbon ca nhm cacbonyl trong phn t xeton b n ng khng gian nhiu hn v in tch dng + cng b gim nhiu bi tc dng ca gc hirocacbon: CH3
+ 1 H C

CH3

2 CH 3

+ 1 > 2

1 O 2 O Do vy, anehit v xeton ngoi nhng tnh cht ho hc ging nhau cn c nhng tnh cht ho hc khc nhau. GV chiu bi tp 2 (SGK) ln mn hnh HS tho lun. 2. Hy so snh nhit nng chy, nhit si v tan trong nc ca anehit, xeton vi ancol tng ng. Gii thch nguyn nhn dn ti s khc nhau gia chng. HS tho lun v a ra kt qu:

dng nguyn cht, gia cc phn t anehit hoc gia cc phn t xeton khng c lin kt hiro. Do vy, nhit nng chy, nhit si ca anehit v xeton thp hn ancol tng ng. Th d: Nhit si (0C)
233

CH3CH2CH=O CH3COCH3 CH3CH2CH2OH

49 57 97,2

trong dung dch th anehit, xeton, ancol u to c lin kt hiro vi cc phn t nc, nn mt s cht c phn t khi nh tan tt trong nc.

Th d: HCH=O, CH3 CH=O CH3COCH3 CH3OH, C2H5OH, C3H7OH

d tan trong nc. tan v hn trong nc. tan v hn trong nc.

GV chiu bi tp 4 (SGK) ln mn hnh HS tho lun. 4. a) Hy nu phng php chung iu ch anehit v xeton. b) Hy vit phng trnh ho hc ca phn ng iu ch anehit fomic, anehit axetic v axeton trong cng nghip hin nay. c) Fomon, fomalin l g ? chng c s dng lm g ? HS tho lun v a ra kt qu: a) phng php chung iu ch anehit v xeton l: Oxi ho ancol bc I v ancol bc II.

Oxi ho hirocacbon.
b) T metan:
t xl CH4 + O2 HCHO + H2O
t 2CH2 = CH2 + O2 2CH3CHO
0

T etilen

T cumen (oxi ho cumen).

CH3CHCH3 + O2
t , xt
t ,Cu
o

OH
0

+ CH3CCH3 O HCHO + H2O

T metanol

CH3OH + O2

c) Fomon, fomalin l dung dch HCHO nng khong 38 40% c dng ngm xc ng vt, thuc da, ty u, dit trng. GV chiu bi tp 5 (SGK) ln mn hnh HS tho lun. 5. Dng phng php ho hc hy nhn bit cc cht trong cc nhm sau, vit phng trnh ho hc cc phn ng xy ra: a) Fomalin, axeton, xiclohexen, glixerol. b) Ancol benzylic, benzen, benzanehit.
234

HS tho lun v a ra kt qu: a) Nhn bit mi cht trong nhm : fomanlin, axeton, xiclohexen, glixerol. Ly mt lng nh ca mi cht cho tc dng vi nc brom th fomalin (dung dch 37% 40% fomanehit) v xiclohexen lm mt mu nc brom, cn axeton v glixerol khng lm mt mu nc brom. Ta tch ring c hai nhm nh: Nhm (1) gm fomalin v xiclohexen. Nhm (2) gm axeton v glixerol. Cho tng cht trong nhm (1) thc hin phn ng trng bc ta phn bit c fomalin v xiclohexen v ch c fomalin thc hin c phn ng trng bc. Cho tng cht trong nhm (2) tc dng vi Cu(OH)2 ta s c glixerol cho dung dch c mu xanh, trong sut. b) Nhn bit mi cht trong nhm: ancol benzylic C6H5CH2OH, benzen C6H6, benzanehit C6H5CHO. Ly mt lng nh ca mi cht cho tc dng vi Na ta nhn ra ancol benzylic, v phn ng c kh H2 bay ra, cn benzen v benzanehit khng phn ng. Thc hin phn ng trng bc vi hai cht cn li th ch c benzanehit tc dng gip ta nhn ra. Cht cn li l benzen. GV chiu bi tp 6 (SGK) ln mn hnh HS tho lun. 6. T qu cy hi ngi ta tch 4-metoxibenzanehit, t qu cy hi hoang tch c p-isopropylbenzanehit, t qu cy vanilla tch c 4-hiroxi-3-metoxi benzanehit (vanilin, dng lm cht thm cho bnh ko). Cho bit nhm metoxi l CH3O. a) Hy vit cng thc cu to ca cc anehit nu trn v nu tng ( + v) ca chng m khng cn cng thc tnh ton. b) Trong 3 cht trn cht no tan trong nc nhiu hn, cht no c nhit si cao nht. V sao ? HS tho lun v a ra kt qu: a) Cng thc cu to ca cc cht trn l: CHO CHO

CHO OCH3 OH

OCH3

CH3CHCH3

4-metoxibenzanehit p-isopropylbenzanehit 4-hiroxi-3-metoxibenzanehit (trong qu cy hi) (trong qu cy hi hoang) (trong qu cy vanilla) Ba cht trn u c + v = 5
235

b) Cht 4-hiroxi-3-metoxibezanehit tan trong nc nhiu hn v cha nhm CH=O v nhm OH u c kh nng to lin kt hiro. GV chiu bi tp 7 (SGK) ln mn hnh HS tho lun.
7. Khi un nng butan vi xc tc ngi ta thu c 3 anken u c cng thc phn t C4H8. Cho 3 anken phn ng vi nc, nhit cao, c xc tc axit, ri oxi ho cc ancol thu c bng CuO nhit cao th thu c hn hp cc ng phn c cng thc phn t C4H8O.

a) Hy vit s phn ng biu din qu trnh nu trn. b) Hy ch r sn phm chnh, ph mi phn ng cho. HS tho lun v a ra kt qu: a) CH3CH2CH2CH3
xt, to

CH2=CHCH2CH3 H 3C C=C H H C=C H 3C H H CH3 CH3

but1-en cis-but-2-en trans-but-2-en

- H2

b)
HOH,H ,t CH2CH2CH2CH3+CH3CHCH2CH3 CH2=CHCH2CH3 OH OH but-1-en
+ o

butan-1-ol (sn phm ph)

butan-2-ol (sn phm chnh)

CH3CHCH2CH3 CH3CH=CHCH3 OH butan-2-ol

CuO,t CH3CH2CH2CHO CH3CH2CH2CH2OH H2 O o

+ o HOH,H ,t

hay C4H8O

butan-1-ol
CuO,t o

butanal hay C4H8O

CH3CCH2CH3 CH3CHCH2CH3 H2 O O OH

butan-2-ol etyl metyl xeton GV chiu bi tp 8 (SGK) ln mn hnh HS tho lun. 8. Cho canxi cacbua phn ng vi nc ri dn kh sinh ra sc qua dung dch
236

gm HgSO4, H2SO4, H2O 800C th thu c hn hp A gm hai cht kh. xc nh hiu sut phn ng ngi ta cho 2,02 g hn hp A phn ng vi dung dch AgNO3 trong amoniac d, th thu c 11,04 g hn hp rn B. a) Hy vit phng trnh ho hc ca cc phn ng xy ra. b) Tnh hiu sut phn ng cng nc vo axetilen trong trng hp nu. HS tho lun v a ra kt qu: Cho CaC2 tc dng vi nc: CaC2 + 2 H2O Ca(OH)2 + C2H2 Khi sinh ra l C2H2 tham gia phn ng tip theo:
HgSO 4 ,80 C C2H2 + H2O CH3CHO
o

(1)

x mol

x mol

(2)

Hn hp A gm hai kh: C2H2 cha tham gia phn ng (y mol) v CH3CHO mi to thnh t (2). Chng u tham gia phn ng (3), (4): CH3CHO + 2[Ag(NH3)2]OH 2Ag + CH3COONH4 + 3NH3 + H2O (3) x mol C2H2 + 2[Ag(NH3)2]OH y mol 2,02g hn hp A 44x + 26y = 2,02 216x + 240y = 11,04 2x mol AgCCAg + 2H2O + 4NH3 y mol 11,04g cht rn B (4)

gii h, c x = 0,04 mol CH3CHO v y = 0,01 mol C2H2 Hiu sut phn ng cng nc vo axetilen: x 100% = 80% H% = x+y GV chiu bi tp 9 (SGK) ln mn hnh HS tho lun. 9. Trong qu trnh bo qun fomalin b c dn, sau lng xung y bnh thnh lp bt mu trng. Phn tch bt mu trng thy C chim 39,95%, H chim 6,67%. un cht bt mu trng vi nc c thm vi git axit th thu c mt dung dch c phn ng trng bc. Hy xc nh cng thc ca bt mu trng v gii thch nhng hin tng nu trn. HS tho lun v a ra kt qu: Theo bi ra c: C : 39,95% ; H : 6,67% ; O : 53,38%.

237

t cng thc CxHyOz. 12x : y: 16z = 39,95 : 6,67 : 53,38 39,95 53,38 : 6,67 : x:y:z= 12 16 x : y : z = 3,329 : 6,67 : 3,36 x:y:z=1 :2 :1 Cng thc n gin nht: CH2O Cng thc phn t: (CH2O)n (Sn phm trng hp). GV chiu bi tp 10 (SGK) ln mn hnh HS tho lun.
10. Hy in ch (ng) hoc S (sai) vo du [ ] mi cu sau:

a) Anehit axetic c sn xut ch yu t axetilen [ ]. b) Axeton c sn xut ch yu bng cch oxi ho propan-2-ol [ ]. c) Fomanehit thng c bn di dng kh ho lng [ ]. d) Ngi ta lau sch sn mu trn mng tay bng axeton. HS tho lun v a ra kt qu: a) S; b) S ; c) S ; d) . GV chiu bi tp 11 (SGK) ln mn hnh HS tho lun.
11. Hy ghp cc tn anehit hoc xeton cho ct bn phi vo cc cu cho ct bn tri.

a) Mi s trong du gi u l ca b) Mi thm c trng ca ko bc h l ca c) Mi thm c bit ca bnh quy l ca d) Mi thm ca qu l ca . HS tho lun v a ra kt qu: a) B ;
Bi tp ngh

A. anehit xinamic B. xitronelol. C. menton D. vanilin

b) C ;

c) D ;

d) A.

1. Hp cht hu c X (cha C, H, O) khng no. Hiro ho hon ton X thu c hp cht hu c Y. un Y trong H2SO4 c 1700C nhn c hp cht Z. Trng hp Z thu c poli isobutilen. Cng thc cu to ca Z l:

A. CH2=C CHO CH3

238

B. CH2=C CHO v CH2=CCH2OH CH3 CH3

C. CH2=CCH2OH CH3

D. CH3CHCHO CH3
p n B.

2. Gi tn hp cht c CTCT nh sau theo danh php IUPAC :

CH3 CH CHCHO OH Cl A. 1-clo-1-oxo-propanol-2. B. 3-hiroxi-2-clobutanal. C. 2-clo-3-hiroxibutanal. D. 2-hiroxi-1-clo-1-oxopropan.

p n C. 3. Hn hp X gm hai cht hu c A, B (Cha C, H, O) l ng phn ca nhau. Bit 14,5 gam hi X chim th tch ng bng th tch ca 8 gam O2 o cng iu kin nhit p sut. Nu cho 14,5 gam X tc dng vi dung dch AgNO3/NH3 d th thu c 10,8 gam kt ta bc. Xc nh % khi lng ca mi cht trong X. A. 85%v 15%. B. 20% v 80%. C. 75% v 25% D. 50% v 50%. p n B. 4. Cho s .

(X) (Y) Etilenglycol. CTCT ph hp ca X, Y l. A. X (C2H6), Y (C2H4). B. X (HCHO), Y (CH2OHCHO).

5. Cho s :

C. X (C2H4), Y(C2H4Cl2). D. C A, B, C.
p n D.

CHO

X Y C. X(OCH3), Y(Cl). D. X(COOH), Y(NO2). p n D.

Cc nhm X, Y c th l. A. X (CH3), Y(NO2). B. X (CH2OH), Y(Br).

6. Hy chn cu pht biu sai.

A. Ch c anehitfomic mi phn ng vi dung dch AgNO3/NH3 theo t l mol 1:4.

239

B. Anehit c tnh oxi ha mnh hn xeton. C. Anehit l sn phm trung gian gia ancol v axit cacboxylic. D. Lin kt i trong nhm cacbonyl (C=O) ca anehit hay xeton phn cc mnh hn lin kt i trong anken. p n A. 7. Cp cht no sau y khi ly cng s mol phn ng vi dung dch AgNO3/NH3 d cho lng kt ta Ag bng nhau? A. HCHO v CH3CHO. B. (CHO)2 v HCOOH. C. HCOOH v HCHO D. HCHO v (CHO)2.
p n D.

240

Bi 60

Axit cacboxylic:

Cu trc, danh php v tnh cht vt l

A. Mc tiu bi hc 1. Kin thc

HS bit:
Khi nim, phn loi, cu to phn t axit cacboxylic. Lin kt hiro, tnh cht vt l ca axit cacboxylic. Vit ng phn v gi tn ca axit cacboxylic.

HS hiu:
Mi lin quan gia cu trc v lin kt hiro ca axit cacboxylic vi tnh cht vt l.
2. K nng

T cng thc bit gi tn v ngc li t gi tn vit c cng thc nhng axit cacboxylic. Vn dng cu trc hiu ng tnh cht vt l v gii ng bi tp.
3. Tnh cm, thi

Thng qua vic nghin cu cc axit cacboxylic, HS cm nhn c mt cch t nhin cc mi quan h bin chng gia cu to v tnh cht, nh hng qua li gia cc nguyn t trong phn t. Gip HS t xc nh c cch sng tt trong x hi.
B. chun b ca GV v HS

GV:

My tnh, my chiu, cc mu axit axetic, axit fomic. M hnh phn t axit axetic, axit fomic.

HS: n tp kin thc v ancol, anehit v xem trc bi axit cacboxylic.

241

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I. nh ngha, phn loi, danh php Hot ng 1 1. nh ngha GV chiu mt s cng thc cu to ca HS quan st nhn xt: mt s axit. HCOOH, CH3COOH, C6H5COOH COOH , CH2=CHCOOH

COOH Yu cu HS nhn xt c im chung ca cc hp cht trn. T nu nh ngha axit cacboxylic.

u c nhm COOH. nh ngha: axit cacboxylic l nhng hp cht hu c m phn t c nhm cacboxyl (COOH) lin kt trc tip vi nguyn t C hoc nguyn t H.

Hot ng 2 2. Phn loi GV cho HS nghin cu SGK v yu cu HS nghin cu SGK v nhn xt: HS nhn xt: C s phn loi axit. Da vo c im cu to gc Axit c chia thnh nhng loi no. hirocacbon v da vo s nhm cacboxylic. Cho v d minh ho. Axit c chia thnh: Lp cng thc tng qut. a) Axit n chc mch h

HCOOH, C2H5COOH CTTQ: CxH2x+1COOH (x 0) CnH2nO2 (n 1) b) Axit khng no n chc CH2=CHCOOH, CH3[CH2]7 CH=CH[CH2]7 COOH c) Axit thm n chc
242

COOH

COOH CH3 COOH

d) Axit a chc HOOC(CH2)4COOH

COOH l axit c nhiu nhm COOH.

Hot ng 3 3. Danh php GV yu cu HS lin h vi cch gi tn HS tho lun tr li. anehit t rt ra cch gi tn thay th axit c cu to mch h. Cch gi tn: a) Tn thay th c cu to: + Cu to cch gi tn. Axit Tn hirocacbon tng oic + Cch chn mch chnh. ng

+ Cch nh s. GV ly v d:
CH 3 CH 2 CH COOH
4 3 2 1

CH3 axit 2-metylbutanoic GV yu cu HS gi tn cc axit cacboxylic HS vit cc ng phn v gi tn. c cng thc phn t C5H10O2. CH3CH2CH2CH2COOH pentanoic

+ Mch chnh ca phn t axit l mch cacbon di nht c cha nhm COOH. + nh s th t bt u t nhm COOH.

CH3CH2CHCOOH 2-metylbutaoic CH3 CH3CHCH2COOH 3-metylbutanoic CH3 CH3 GV gii thiu cch gi tn thng thng: CH CCOOH 2,2-imetylpropanoic 3 thng lin quan n ngun gc tm ra CH3 n. V d: HS nghe ging, ghi bi HCOOH axit fomic (theo ngun gc tm ra n t kin la).
243

CH3COOH axit axetic (c trong dm n). GV b sung cch gi tn ca mt s axit khc nh: COOH COOH COOH axit benzoic CH2= CCOOH CH3 axit oxalic axit metacylic

GV cho HS luyn cch gi tn bng cch gi tn cc axit c trong bng 9.1

HS gi tn cc axit c trong bng 9.1 SGK.

II. Cu trc v tnh cht vt l Hot ng 4 1. Cu trc GV Chiu m hnh phn t axit fomic HS quan st v nhn xt: v axit axetic (Hnh 9.2) ln mn hnh Cu to nhm COOH cho hc sinh quan st. O

O H

a)

b)

Yu cu HS nhn xt: Cu to ca nhm COOH. D on s chuyn e trong COOH. Mc phn cc ca lin kt OH trong ancol, phenol v trong phn t axit cacboxylic.

Gm c mt nhm cacbonyl (>C=O)v mt nhm hiroxyl (OH). D don: do tng tc gia nhm cacbonyl v nhm hiroxyl lm cho mt electron nhm cacbonyl chuyn dch c m t nh sau:
O

R C

O .. H

244

 Lin kt OH trong axit phn cc mnh hn so vi ancol v phenol. Mc linh ng ca nguyn t H

GV hng dn HS phn tch mi quan axit cacboxylic > phenol > ancol h gia cu trc v tnh cht ca axit HS tho lun v nhn xt: Do s tng tc ca nhm cacbonyl v nhm cacboxylic. hiroxyl m kt qu lm cho nguyn t H nhm OH axit tr nn linh ng hn nhm OH trong ancol, phenol v nhm C=O ca axit cng khng ging nhm C=O ca anehit, xeton.
Hot ng 5 2. Tnh cht vt l GV cho HS quan st mu axit axetic, HS quan st v nhn xt: axit fomic v lm th nghim ho tan C hai axit u l cht lng, khng vo nc. Yu cu HS rt ra nhn xt mu. v: Hai axit tan tt trong nc. Trng thi ca axit iu kin HS h thng li tnh cht vt l ca thng. axit tan axit axetic, axit fomic. u l cht lng hoc rn.

GV ghi nhn kin b sung, yu cu Nhit si ca cc axit tng dn HS tng kt li tnh cht vt l ca axit khi phn t khi axit tng. cacboxylic. Ba axit u tan v hn trong nc, tan gim dn khi s nguyn t C tng. Mi axit u c v chua ring, th GV Chiu bng sau ln mn hnh 0 d: Cht CTPT ts axit axetic c v chua ca gim, axit propan C 3H 8 42 xitric c v chua ca chanh propanal CHO 48
3 6

axeton propanol propanoic

C 3H 6O C 3H 8O C 3H 6O 2

56 97,2 141

245

Yu cu HS nhn xt v im si ca cc cht trn ? GV t vn : Ti sao axit cacboxylic c nhit si cao hn ancol, anenhit, axeton, ankan c cng nguyn t cacbon. GV iu khin v hng dn HS gii quyt vn : Yu t no lm cho ancol c nhit si cao hn hirocacbon tng ng. Axit c kh nng c lin kt hiro khng? Liu lin kt hiro trong axit c c im no khc ancol.

HS nhn xt: im si axit cacboxylic cao hn ancol, anenhit, axeton, ankan c cng nguyn t cacbon.

HS tham gia gii quyt vn :

Ancol c lin kt hiro.

Axit c hiro linh ng nn c lin kt hiro. Do axit c lin kt hiro bn hn GV ghi nhn kin b sung: Axit c lin kt hiro bn hn ancol. ancol, cc cht khc u khng c lin kt hiro, v vy nhit si ca axit Ngoi kiu lin kt hiro ging ancol, rt cao. axit cn c kiu lin kt hiro dng ime rt bn:

C R O OH Lin kt hiro bn lm cho nhit si HS ghi bi. ca axit cao. RC

Hot ng 6 Cng c bi v bi tp v nh 1. Cng c bi

O HO

GV khc su mt s kin thc cho HS v: Cng thc chung, cch phn loi axit cacboxylic. Cu to ca axit cacboxylic c lin kt OH phn cc mnh hn ancol, phenol.
Cc loi ng phn, quy tc gi tn axit cacboxylic.
246

 Axit cacboxylic c nhit si cao hn ancol, anenhit, axeton, ankan c cng nguyn t cacbon. Do axit cacboxylic c lin kt hiro rt bn. GV chiu cc bi tp sau ln mn hnh cho HS tho lun. 1. Gi tn hp cht c CTCT nh sau theo danh php IUPAC:

C2H5 CH3 CH CH2 CH COOH C2 H 5 A. 2,4-ietylpentanoic. B. 2-metyl-4-etylhexanoic. C. 2-etyl-4-metylhexanoic. D. 2-metyl-5-cacboxiheptan.

p n B 2. Axit no sau y c ng phn hnh hc:

A. CH2=CHCOOH. B. CH3CH=CHCOOH.

C. CH2=CH(CH3)COOH. D. C A, B, C.
p n B

3. Cht no sau y c nhit si thp nht.

A. Axit fomic. C. Axit propionic.

4. Cht no sau y l axit metacrylic?

B. Axit axetic. D. Axit isobutylic.

p n A.

A. CH2=CHCOOH. C. CH3CH(OH)COOH.
2. Bi tp v nh 1, 2, 3, 4, 5 (SGK)

B. CH2=CH(CH3)COOH. D. HOOCCH2COOH.
p n B

D. Hng dn gii bi tp SGK 1. a) ; 3. a) C5H10O2

b) S;

c) S;

d)

CnH2nO2 l cng thc tng qut ca axit no, n chc hoc este no, n chc y ch vit ng phn axit. : axit pentanoic CH3 CH2CH2CH2COOH

247

CH3CH2 CH COOH CH3 CH3 CH CH2COOH CH3 CH3 CH3 C COOH CH3

: axit 2-metylbutanoic

: axit 3-metylbutanoic

: axit 2,2-imetylpropanoic

b) C4H6O2 CnH2n 2O2 l cng thc tng qut ca axit n chc khng no, este n chc khng no, y ch vit ng phn axit. CH2=CHCH2COOH CH3CH=CHCOOH CH2 = C COOH
4. HOOCCHCH2COOH OH

: axit but-3-enoic : axit but-2-enoic : axit 2-metylpropenoic : axit 2-hiroxibutanioic (axit malic) : axit 2,3-ihiroxibutanioic (axit tactric) : axit 2-hiroxipropan-1,2,3- tricacboxylic (axit xitric) .. O > H H phn cc mnh, th

HOOCCHCHCOOH OH COOH HOOCCH2C CH2 COOH OH

5. a) Lc axit:
+

R C

H > C 2H 5 O H

O ..

Cc hiu ng trn th hin cht no c lin kt O tch ra ion H+ d dng hn nn lc axit ln hn.

b) Nhit si, nhit nng chy ca axit cao hn v c kh nng to lin kt hiro lin kt phn t bn vng hn.

248

Bi 61

Axit cacboxylic:

Tnh cht ho hc, iu ch v ng dng

A. Mc tiu bi hc 1. Kin thc

HS bit: Vn dng kin thc hc vo phn ng ca gc hirocacbon ca axit cacboxylic. Phng php iu ch v ng dng ca axit cacboxylic. Bit tnh cht ho hc c trng ca axit cacboxylic v ng dng ca mt s axit cacboxylic. HS hiu: Mi lin quan gia cu trc v tnh cht ca nhm COOH.

Tnh axit v nh hng ca nhm th (phn li thun nghch trong dung

dch, xt hng s Ka, nh hng ca gc th n Ka). Phn ng to thnh cc dn xut axit (tc dng vi ancol to thnh este, tch nc lin phn t). Phn ng gc hirocacbon (no, khng no, thm).
2. K nng

Tin hnh th nghim, quan st th nghim, m hnh, rt ra nhn xt v cu to v tnh cht. Vn dng cu trc hiu ng tnh cht ho hc v gii ng bi tp. Vn dng tnh cht chung ca axit v ca axit axetic nu tnh cht ho hc ca axit cacboxylic. Nhn xt s liu, th rt ra quy lut.
3. Tnh cm, thi

Thng qua bi hc lm cho HS thy r phi c kin thc v axit s dng hp l axit cacboxylic phc v con ngi mt cch an ton, ng thi bo v mi trng.
249

B. chun b ca GV v HS

GV: My tnh, my chiu, cc phiu hc tp.

Ho cht:

+ Axit axetic. + Giy qu tm. + Na kim loi. + ng nghim. + B gi th nghim.

+ Axit fomic. + Mu CaCO3. + Nc ct. + ng ht nh git.

Dng c:

HS: n tp kin thc bi anehitxeton.

C. tin trnh dy hc Hot ng ca GV Hot ng 1 Kim tra bi c Hot ng ca HS

GV chiu hai bi tp sau ln mn hnh HS ln bng trnh by. v yu cu HS tho lun. 1. Vit cng thc cu to thu gn v HS 1 vit ng phn v gi tn: gi tn cc axit c CTPT: C5H10O2. CH3CH2CH2CH2COOH pentanoic CH3CH2CHCOOH 2-metylbutanoic CH3 CH3CHCH2COOH 3-metylbutanoic CH3 CH3 CH3CCOOH 2,2-imetylpropanoic CH3 2. Cho axit X c cng thc cu to (CH3)2CHCH2CH2COOH tn ca X l: A. axit 2-metylbutyric. B. axit 2-metylbutanoic. C. axit 4-metylpentanoic. D. axit isohexanoic.
250

HS 2:

p n C.

i. Tnh cht ho hc Hot ng 2 1. Tnh axit v nh hng ca nhm th GV chiu cng thc cu to ca axit HS quan st v nhn xt (dng hnh fomic v axetic ln mn hnh. sau):

Yu cu HS nu cc hiu ng chuyn Cc hiu ng trn lm cho lin kt OH phn cc mnh v c kh nng phn li dch electron trong nhm cacbonyl. tch ra ion H+. GV cho HS nghin cu thng tin sau: axit HCl 0,1M c pH =1. axit RCOOH 0,1M c pH > 1. Yu cu HS nhn xt v: Tnh axit ca hai axit trn.
Phng trnh phn li. Biu thc tnh hng s phn li. ngha ca i lng Ka.

HS nhn xt: Chng t HCl phn li hon ton. Chng t RCOOH phn li khng hon ton (phn li mt phn). Phng trnh phn li. RCOOH+H2O U RCOO + H3O+ Ka = [H 3O + ][RCOO ] [RCOOH]

GV b sung: Gi tr Ka ph thuc vo mc phn cc ca lin kt OH, lin kt OH cng phn cc th cng d phn li ra ion H+, ion cacboxylat sinh ra cng bn. GV yu cu HS nu tnh cht ho hc chung ca axit.

Ka l mc o lc axit: Ka cng ln th axit cng mnh.

HS nhn xt: Lm qu tm chuyn thnh mu .

Tc dng vi kim loi ng trc hiro. Tc dng vi baz, oxit baz. Tc dng vi mui ca axit yu hn.

GV ln lt lm cc th nghim th HS quan st v rt ra kt lun: tnh cht ca axit axetic.

251

 Cho mt mu qu vo ng nghim ng axit CH3COOH. Cho mt t bt vi vo ng nghim ng axit axetic. Ngm mt l km mng vo dung Axit cacboxylic th hin y tnh dch axit axetic. cht ca mt axit. GV hng dn HS kt lun tnh cht ho hc ca axit axetic.

GV chiu bng sau ln mn hnh: TT 1 2 3 4 5 6 axit HCOOH CH3COOH C2H5COOH CH3[CH2]4COOH ClCH2COOH F CH2COOH Ka (25oC) 17,72.105 1,75.105 1,33.105 1,29.105 13,5.105 26,9.105

GV t vn : Ti sao gi tr hng s Ka ca cc axit khc nhau v yu t no quyt nh n gi tr hng s Ka ca axit cacboxylic. GV hng dn, iu khin HS gii quyt vn : Cc axit trn c c im no ging v khc nhau. So snh cu to cc axit 1, 2, 3, 4 tm quy lut bin i Ka. Dng hiu ng chuyn electron gii thch. So snh cu to cc axit 2, 5, 6 v tm quy lut bin i Ka.

HS tham gia gii quyt vn : + Ging nhau: u c 1 nhm cacboxyl. + Khc nhau: cu to gc axit. Cc axit 1, 2, 3, 4 l axit no n chc khi s C trong gc axit (R) tng th Ka gim.

Gc R (ankyl) y electron v pha nhm cacboxyl nn lm gim mc

252

phn cc ca lin kt OH (gim lc axit). Cc axit 5, 6 c cc nguyn t halogen c m in ln ht electron khi nhm cacboxyl nn lm tng lc axit.
Hot ng 3 2. Phn ng to thnh dn xut axit a) Phn ng vi ancol (phn ng este ho)

GV thit k hot ng theo mt trong cc cch sau: Cch 1: GV m t th nghim: un si 1 mol CH3COOH v 1 mol C2H5OH (c thm 1 ml H2SO4 m c). Sau 6 n 8 gi ngi ta quan st thy s mol este hu nh khng thay i v bng 0,67 mol (bit phn ng trn l phn ng thun nghch). T th nghim trn ta c kt lun g? Vit phng trnh ho hc minh ho. GV b sung: Phng trnh ho hc tng qut.
H2SO4 ZZZ X H2O RCOH +HOR1 Y ZZ o Z RCOR1+ t O O

HS: Nghe ging v tho lun.

Phn ng gia axit cacboxylic vi ancol l phn ng thun nghch, khi s mol este bng 0,67 l phn ng t n trng thi cn bng. Phng trnh ho hc.
H 2 SO 4 ZZZ X CH3COOH + C2H5OH YZZ o Z t

CH3COOC2H5+ H2O etylaxetat

HS: Nghin cu th nghim v tho lun. GV yu cu HS nghin cu th Phng trnh phn ng l: H 2 SO 4 nghim trong SGK v gi cho HS CH COOH + C H OH ZZZ X YZZ 3 2 5 o Z t bit phn ng th nhm OH ca axit CH3COOC2H5 + H2O cacboxylic l phn ng thun nghch. etylaxetat GV yu cu HS vit phng trnh ho H SO 2 4 hc ca th nghim trn v rt ra RCOH+HOR ZZZ X 1 YZZ o Z RCOR1+ H2O t phng trnh tng qut ca phn ng O O gia axit cacboxylic vi ancol.
253

Cch 2:

GV: Phn ng este ho l phn ng HS tho lun: thun nghch, hy ngh cc phng + Thm axit cacboxylic hoc ancol. php lm tng lng este. + Tch este hoc nc ra khi mi trng phn ng. GV b sung: tng hiu sut ca phn ng este ngi ta thng tch este ra khi mi trng phn ng bng phng php un nng v este d bay HS tho lun: H2SO4 lm xc tc phn ng xy ra hi. GV yu cu HS phn tch tc dng ca nhanh hn v H2SO4 c ht nc lm phn ng chuyn dch theo chiu to este. H2SO4 trong phn ng este ho. b) Phn ng tch nc lin phn t GV m t phn ng tch nc ca HS vit phng trnh ho hc: P2 O5 axit: CH3COH+HOCCH3 Khi cho axit axetic tc dng vi P2O5, O O hai phn axit tch i mt phn t CH3COCCH3 + H2O nc, tao thnh anhirit axit. O O Yu cu HS vit phng trnh ho hc anhirit axetic minh ho.
Hot ng 4 3. Phn ng gc hirocacbon GV yu cu 1 HS phn loi gc axit. HS nhn xt: Gc no. Gc thm.

GV gii thiu: sau y chng ta s xt Gc khng no. tnh cht ho hc ca tng loi gc. a) Phn ng th gc no GV yu cu HS d hc ca gc ankyl. GV b sung: iu kin phn (P) lm xc tc. Phn ng th u H ca nguyn t C
254

on tnh cht ho HS tho lun: Gc ankyl c tnh cht ho hc tng t ankan c phn ng c trng l phn ng dng photpho ng th. tin th nguyn t Phng trnh ho hc: v tr (C bn

P cnh nhm COOH), yu cu HS vit CH3CH2CH2COOH + Cl2 phng trnh ho hc. CH3CH2CHCOOH + HCl GV lu HS: Nu trong iu kin ch Cl chiu sng khng c xc tc th phn ng th u tin vo v tr :

CH3CH2CH2COOH + Cl2
CH3CH2CHClCOOH (5%)

as - HCl

CH3CHClCH2COOH (64%)

ClCH2CH2CH2COOH (31%) b) Phn ng th gc thm GV gii thiu: nhm cacboxyl vng HS nghe GV gii thiu v vit phng benzen nh hng cho phn ng th trnh ho hc: vo v tr meta v lm cho phn ng th kh khn hn so vi th vo COOH COOH benzen. H2SO4 +H2O +HNO3 Yu cu HS vit phng trnh ho hc NO2 minh ho. c) Phn ng cng vo gc khng no GV gi : Axit khng no tham gia HS tho lun v hon thnh cc phng phn ng cng H2, Br2, Cl2 nh trnh ho hc: hirocacbon khng no. Yu cu HS vit tip v phi ca cc CH2=CHCOOH+Br2CH2CHCOOH phng trnh ho hc sau y: Br Br CH2=CHCOOH + Br2 CH3[CH2]7CH=CH[CH2]7COOH + H2 CH2=CHCOOH + HBr CH3[CH2]7CH=CH[CH2]7COOH+ H2

CH3[CH2]7CH2CH2[CH2]7COOH GV b sung tn gi ca cc sn phm CH =CHCOOH + HBrCH CH COOH 2 2 2 to thnh v lu HS: Khi nhm Br COOH gn trc tip vo ni i C=C th phn ng cng cho sn phm chnh ngc quy tc Mac-cp-nhi-cp.

255

II. iu ch v ng dng Hot ng 5 1. iu ch a) Trong phng th nghim

GV t vn : Bng kin thc hc HS tho lun v a ra cc kin. qua v hirocacbon, dn xut halogen, ancol, anehit, xeton. Yu cu HS c th ngh phng trnh ho hc iu ch axit t mt trong s cc hp cht c th nu trn. GV ghi nhn cc kin ca HS, phn Phng trnh ho hc: loi v lp thnh cc s sau. 1. C2H6 + Cl2 C2H5Cl + HCl 1. C2H6 C2H5Cl C2H5OH CH3CHO CH3COOH. 2. C6H5CH3 C6H5COOK C6H5COOH 3. RX RCN RCOOH GV yu cu HS c th ho cc s trn. C2H5Cl + NaOH C2H5OH + NaCl C2H5OH + CuO CH3CHO + Cu + H2O 2CH3CHO + O2 2CH3COOH 2. C6H5CH3 + 2KMnO4 C6H5COOK + 2MnO2 + KOH + H2O C6H5COOK + HCl C6H5COOH + KCl GV b sung cc iu kin phn ng 3. RX + KCN RCN + KX cho HS hon thin cc phng trnh RCN + 2H2O RCOOH + NH3 ho hc. b) Trong cng nghip GV cho HS nghin cu v yu cu HS HS nghin cu SGK v nhn xt: nhn xt v:
Phng php c truyn dng sn Phng php ln men gim. xut axit axetic l g? Phng trnh ho hc: men gim Vit phng trnh ho hc? C2H5OH+O2 CH3COOH+H2O GV: y l phng php ch dng sn xut lng nh axit axetic lm gim n.
256

GV: Phng php no l phng php HS: Oxi ho anehit axetic. xc tc ch yu sn xut axit axetic. 2CH3CHO + O2 2CH3COOH Vit phng trnh ho hc?
xc tc Nu phng trnh tng qut iu ch 2RCHO + O 2RCOOH 2 axit t anehit tng ng GV gii thiu: Phng trnh tng qut HS nghe ging: oxi ho ct mch ankan: 2RCH2CH2 R'+5O22RCOOH + 2CH3 CH2 CH2CH3 + 5O2 2R'COOH + H2O 2CH3 COOH + 2 H2O Vit phng trnh phn ng vi butan. GV gii thiu: Phng php i t metanol c coi l phng php hin i sn HS vit phng trnh ho hc iu ch xut axit axetic (v metanol v cacbon axit axetic t metanol. xt CH3COOH oxit u c iu ch t metan c sn CH3OH + CO o t trong thin nhin). Vit phng trnh ha hc?

Hot ng 6 2. ng dng

GV: Su tp tranh, nh, mu vt. Chiu ln mn hnh cho HS quan st v yu cu HS nu cc ng dng chnh ca axit cacboxylic. GV phn tch cc li ch m chng em li, bn cnh cn bit tnh c hi ca n n con ngi v mi trng.

HS nhn xt: Lm nguyn liu cho cng nghip m phm, cng nghip dt, cng nghip ho hc.

Hot ng 7 Cng c bi v tp v nh 1. Cng c bi GV nhc li cc ni dung cn nm vng cho HS:

Tnh axit v nh hng ca nhm th:

+ Nhm ht electron lm tng tnh axit.

257

+ Nhm y electron lm gim tnh axit. Phn ng to thnh dn xut axit. Phn ng vi ancol l phn ng thun nghch (xy ra khng hon ton) Cc phn ng gc axit. Phng php iu ch mi v ng dng ca axit hu c. GV chiu ln mn hnh cc bi tp sau HS tho lun. 1. Sp xp theo th t tng dn tnh axit cc cht sau: CH3CH2COOH (1), CH3COOH (2), CH2=CHCOOH (3). A. (1) < (2) < (3). C. (1) < (3) < (2). B. (2) < (3) < (1). D. (3) < (1) < (2).
p n A. 2. Cho 24,6 g hn hp CH3COOH, HOOCCOOH, C6H5OH tc dng va vi 300ml dung dch KOH 1M. Tnh tng khi lng mui thu c? A. 16,2 gam. B. 30 gam. C. 36 gam. D. 41,1 gam. p n C. 3. Hn hp X gm 2 axit no A v B. t chy hon ton 0,2 mol X cn 2,24l O2(ktc). Mt khc 0,1 mol X tc dng va vi 150 ml dung dch Na2CO3 0,5M. CTCT ca hai axit l: B. HCOOH v HOOCCOOH. A. HCOOH v CH3COOH.

D. CH3COOH v HOOCCH2COOH. p n B. 4. C 5 bnh ng 5 cht lng sau: dung dch HCOOH, dung dch CH3COOH, ancol etylic, glixerol v dung dch anehit axetic. Dng nhng ha cht no sau y nhn bit c 5 cht lng trn. A. AgNO3/NH3, qu tm. C. AgNO3/NH3, Cu(OH)2. B. Nc brom, Cu(OH)2. D. Cu(OH)2, Na2CO3.
p n D. 5. Phn ng no di y c th xy ra trong dung dch nc?

C. CH3COOH v HOOCCOOH.

(1) CH3COOH + NaOH (2) CH3COOH + Na2CO3 (4) CH3COOH + C6H5ONa (3) CH3COOH + NaHSO4 (5) CH3COOH + C6H5COONa A. (1), (2), (4).
258

B. (1), (2), (3).

C. (1), (2), (5).

D. (1), (2), (3), (4), (5).

p n A.

2. Bi tp v nh 1, 2, 3, 4, 5, 6, 7, 8, 9 (SGK) D. Hng dn gii bi tp SGK 1. b) 2CH3COOH + Na2CO3 2CH3COONa + CO2 + H2O ONa OH

+ CO2 + H2O

+ NaHCO3

2. a) b) S c) d) S 3. a) CH3COOH < ClCH2COOH < Cl2CHCOOH < Cl3CCOOH

b) CH3CH2CH2COOH < ClCH2CH2CH2COOH < CH3CH(Cl)CH2COOH < < CH3CH2CH(Cl)COOH. + 4. Gii thch: HCl phn li hon ton, nng H ln, tc phn ng ln, H2 thot ra nhanh hn. CH3COOH phn li km (K= 1,75.105), nng H+ nh, tc phn ng nh, sau 1 pht lng H2 sing ra t hn. Mg + 2HCl MgCl2 + H2 (1) 1 mol 0,5 mol Mg + 2CH3COOH (CH3COO)2Mg + H2 (2) 1 mol 0,5 mol V s mol H2 thot ra bnh (A) v bnh (B) lc kt thc phn ng l bng nhau nn sau 10 pht hai bng cao su c th bng nhau. 5. a) C6H5ONa + CH2=CHCOOH CH2=CHCOONa + C6H5OH b) NaHCO3 + CH2=CHCOOH CH2=CHCOONa + CO2 + H2O
Ni CH3CH2COOH c) CH2=CHCOOH + H2 o t

d) CH2= CH COOH + Br2 CH2BrCHBrCOOH

P2 O5 (CH2=CHCO)2O + H2O e) 2CH2=CHCOOH

anhirit acrylic
trng hp g) nCH2=CHCOOH

CH CH2 n COOH

6. a) CH3CHO + HCN CH3CH CN

OH
259

H ,t CH3CH CN + 2H2O CH3CH COOH + NH3 OH OH

o

ete b) C2H5Br + Mg C2H5MgBr C2H5MgBr + CO2 C2H5COOMgBr C2H5COOMgBr + HCl C2H5COOH + MgClBr 7. Nhn bit

a) Thuc th v kt qu c trnh by trong bng: C2H5OH Qu tm Na AgNO3/NH3 H2 Ag cn li HCHO CH3COCH3 CH3COOH ho

b) Thuc th v kt qu c trnh by trong bng: C2H5OH Qu tm AgNO3/NH3

8. Phng trnh ho hc:

O2NC6H4CHO Ag

C6H5COOH ho

cn li

CH3COOH + NaOH CH3COONa + H2O 0,025 mol 0,025 mol 0,025.60 C% = .100% = 3,75% 40,0
9. a) Nng mol/l ca dung dch thu c:

Khi lng CH3COOH nguyn cht : 1,05.10,0= 10,5 (g) Hay 10,5 : 60 = 0,175 (mol) Nng mol ca dung dch thu c: 0,175 : 1,75 = 0,1 (mol) b) in li ca CH3COOH dung dch trn CH3COOH U CH3COO + H+ (hoc H3O) ban u phn ng cn bng
260

0,1 0,1 0,1(1 )

0 0,1 0,1

0 0,1 0,1

pH = 2,9 [H+] = 10pH = 102,9 = 0,126.102 [H3O+] = 0,1 = 0,126.102 = 0,126.101 c) Tnh Ka 250C Ka
[C 3C ][ 3 + ] 0,1..0,1. 0,1. 2 = = [C 3C] 0,1.(1 ) 1
0,1.(0,126.10 1 ) 2 1,58.10 5 1 0,126.10 1

Ka =

E. t liu tham kho

Tnh axit ca axit cacboxylic ph thuc rt nhiu vo hiu ng electron ca gc hidrocacbon. Gc hidrocacbon cng ht electron th lin kt OH cng phn cc d phn li ra ion H+, ion cacboxylat sinh ra cng bn, Ka cng tng ln. Ngc li, nu gc hirocacbon cng y electron th lin kt OH cng km phn cc v kh phn li ra ion H+, ion cacboxylat sinh ra cng km bn, dn n Ka cng gim. C th so snh tnh axit gia cc loi axit cacboxylic da trn mt s quy lut sau(1): 1. Dy axit bo, no, c hiu ng +I hoc + H lm gim Ka: HCOOH > CH3COOH > CH3CH2COOH pKa: 3,77 4,76 4,88 2. Dy axit bo, no, c nhm ht electron (I) lm tng Ka: F CH2COOH < NC CH2COOH < O2N CH2COOH < F3C COOH pKa: 2,57 2,4 1,68 0,23 3. Axit cacboxylic c nhiu nhm ht electron (I) cng lm tng Ka: F3C COOH > F2CH COOH > F CH2 COOH pKa: 0,23 1,24 2,57 4. Nhm th (I) cng gn nhm cacboxyl th Ka cng tng: CH3CH2CHCOOH < CH3CHCH2COOH < CH2CH2CH2COOH Cl Cl Cl pKa: 2,84 4,06 4,52 5. Axit khng no c hiu ng I v +C c Ka ln hn cc axit no tng ng v m in ca chng khc nhau:
(1) Xem thm: Cao C Gic. Tuyn tp bi ging ho hu c - Nxb HQG H Ni, 2001.

261

HC C COOH > CH2 = CH COOH > CH3CH2COOH pKa: 1,84 4,25 4,88 6. Axit khng no c lin kt bi cc v tr khc nhau c tnh axit mnh, yu khc nhau: CH3CH = CHCH2COOH > CH2CH2CH = CH COOH (I) (I, +C) pKa: 4,48 4,83 7. Axit khng no dng cis lun c tnh axit mnh hn dng trans do hai nhm th dng cis c s tng tc vi nhau: CH3 C=C H pKa: 4,08 HOOC C=C COOH HOOC C=C H H 4,82 H COOH CH3 C=C COOH H

H COOH H H pKa: 1,91 3,91 8. Khi thay H trong axit fomic HCOOH bng cc gc hirocacbon khc nhau , CH 3 , C6H5CH2, ta c: C 6 H5 HCOOH > (I, C = 0) COOH > (I, +C) CH2COOH > CH3COOH (I) (+I)

pKa: 3,77 4,20 4,30 4,76 9. Axit benzoic c nhm th trong vng benzen cc v tr khc nhau c tnh axit mnh yu khc nhau. pKa ca mt s axit benzoic th. V tr Axit CH3C6H4COOH H2NC6H4COOH FC6H4COOH ClC6H4COOH BrC6H4COOH
262

o 3,91 4,97 3,27 2,92 2,85

m 4,27 4,78 3,87 3,82 3,81

p 4,36 4,92 4,14 3,98 3,97

IC6H4COOH HOC6H4COOH CH3OC6H4COOH NCC6H4COOH O2NC6H4COOH

2,86 2,97 4,09 3,14 2,16

3,85 4,06 4,09 3,84 3,47

4,02 4,48 4,47 3,55 3,41

Qua bng trn c th rt ra mt s nhn xt: Cc nhm th v tr ortho (d ht electron hay y electron) u lm tng tnh axit so vi axit benzoic (pKa = 4,20). Hiu ng c bit ny gi l hiu ng ortho. Hiu ng ortho l t hp ca nhiu loi hiu ng (hiu ng cm ng, hiu ng khng gian, hiu ng trng v lin kt hiro). Cc nhm th v tr meta v para ca axit benzoic lm thay i tnh axit theo quy lut: cc nhm th c hiu ng +I, +C hay +H (y electron) lun lm gim tnh axit; Cc nhm th c hiu ng I hay C (ht electron) lun lm tng tnh axit. Hai nhm th NO2, CN v tr para th c hai hiu ng I v C u pht huy c tc dng cho nn tnh axit tng hn v tr meta, v tr meta cc nhm th ny ch c hiu ng I, cn hiu ng C khng pht huy c tc dng. Ngoi cch da vo hiu ng gii thch tnh axit cn c th da vo n nh ca anim cacboxylat, khi cc nhm th ny v tr para s n nh hn v tr meta. i vi cc nhm th OH v OR th v tr para chng pht huy c c hai hiu ng I v +C nn tnh axit gim. Khi cc nhm th ny v tr meta, ch yu ch c hiu ng I nn tnh axit tng. Cc halogen (F, Cl, Br, I) gn vo nhn benzen c hiu ng I mnh hn +C. v tr meta, chng ch c hiu ng I nn tnh axit tng, cn v tr para, hiu ng I mnh hn +C lm cho tnh axit gim hn v tr meta.

263

Bi 62

luyn tp Axit cacboxylic

A. Mc tiu bi hc 1. Kin thc

Thng qua vic h thng ho kin thc v luyn tp lm cho HS: Hiu thm v mi quan h gia cu trc vi tnh cht vt l, tnh cht ho hc v phng php iu ch ca axit cacboxylic. Bit cc ng dng thng thng ca axit cacboxylic. Vn dng gii bi tp nhn bit, so snh.
2. K nng

Rn luyn k nng so snh, tm mi lin h gia kin thc c bn lp s tng kt, t c cch nh h thng. K nng c lp suy ngh, vn dng kin thc hc t bit cch gii ng bi tp.
3. Tnh cm, thi

Gip HS nhn thc c cc cht hu c gn gi vi i sng v nhng hiu bit v chng l rt cn thit, gip chng ta s dng hp l, c hiu qu cc sn phm ho hc, t tng dn lng yu thch b mn.
B. chun b ca gv v hs

GV: HS:

My tnh, my chiu, h thng cc cu hi v bi tp n tp. n tp bi cc bi anehit-xeton v axit cacboxylic. Chun b trc ni dung luyn tp nh.

264

C. tin trnh dy hc Hot ng ca GV Hot ng ca HS

I. Kin thc cn nm vng Hot ng 1

GV nu cc vn c bn hc: HS lng nghe v chun b cc ni dung Mi lin quan gia cu trc v tnh luyn tp. cht ca axit cacboxylic. c im cu trc lin kt nhm COOH. S chuyn ho gia cc hp cht hu c hc. GV: Chia HS theo cc nhm (4 nhm) v v giao ni dung luyn tp cho cc nhm. GV yu cu HS (nhm 1) nu tnh HS (nhm 1) tho lun v nhn xt. cht ho hc ca axit cacboxylic. Axit cacboxylic c tnh cht: Tnh axit yu: + Phn li thun nghch. + C tnh cht ca mt axit (tc dng vi kim loi, baz, oxit baz, mui ca axit yu hn). Phn ng to thnh dn xut axit. + Phn ng vi ancol (phn ng este ho). + Phn ng tch nc lin phn t. Phn ng gc hirocacbon. + Phn ng th gc no. + Phn ng gc thm. + Phn ng ca gc khng no. GV yu cu HS (nhm 2) vit phng HS (nhm 2) tho lun v nhn xt. trnh ho hc minh ho tnh cht ho hc Phng trnh ho hc: ca axit cacboxylic m nhm 1 nu.
265

RCOOH + H2O U RCOO + H3O+ RCOOH + NaOH RCOONa + H2O 2RCOOH + Mg (RCOO)2Mg + H2
2 4 ZZZ X RCOOH+ROH YZZ o Z RCOOR+ H2O t H SO P2 O5 2RCOOH (RCO)2O + H2O

CH2=CHCOOH + Br2 CH2CHCOOH Br Br GV yu cu HS (nhm 3) nu phng HS (nhm 3) tho lun v nhn xt. php iu ch v ng dng ca axit Cc phng php iu ch: cacboxylic. Trong phng th nghim. + Oxi ho hirocacbon, ancol bc I. + T dn xut halogen. Trong cng nghip. + Ln men gim. + Oxi ho anehit. + i t metanol. GV yu cu HS (nhm 4) vit phng HS (nhm 4) tho lun v nhn xt: trnh ho hc dng iu ch axit T hirocacbon. cacboxylic m nhm 3 nu. C2H6 + Cl2 C2H5Cl + HCl C2H5Cl + NaOH C2H5OH + NaCl T ancol. C2H5OH + CuO CH3CHO + Cu + H2O 2CH3CHO + O2 2CH3COOH T dn xut halogen. RX + KCN RCN + KX RCN + 2H2O RCOOH + NH3 Ln men gim. 1 C2H5OH + O2 CH3COOH + H2O 2 Oxi ho anehit.
266

xc tc 2RCHO + O2 2RCOOH

Oxi ho ct mch ankan. 2CH3 CH2 CH2CH3 + 5O2 2CH3 COOH + 2 H2O T metanol.
xt CH3OH + CO CH3COOH o t

GV nhn xt kt qu trnh by ca cc nhm v chiu s tng kt kin thc sau HS t h thng ho kin thc v axit cacboxylic.
S chuyn ho ca axit cacboxylic

RCOO + H3O+ H 2O P 2O 5 (RCO)2O H2O H 3O + KCN

RCOO + H2O OH Mg ROH

H+, to

(RCOO)2Mg + H2

RCOOH

RCOOR + H2O

O2/ xt/ t0

O2/ xt/ t0

O2/ xt/ t0

R X

R C N

RCH2CH2R

RCH2OH

RCHO

II. bi tp Hot ng 2

GV chiu bi tp 1 (SGK) ln mn hnh cho HS tho lun. 1. Hy in cc t ng thch hp vo cc ch trng trong on vn vit v cu trc nhm cacboxyl sau y:
267

Nhm cacboxyl c hp bi(1)v(2)Do mt eletron dch chuyn t nhm(3)..v, nn nhm(4) axit cacboxylic km hot ng hn nhm(5) anehit v (6), cn nguyn t H nhm(7)axit th linh ng hn nhm OH (8) v nhm(9)phenol A: ancol; B: OH; C: nhm hiroxyl; D: nhm cacboxyl; E: C=O; G: xeton. (ch mi cm t c th c dng nhiu ln). HS tho lun v a ra kt qu: Nhm cacboxyl c hp bi nhm cacbonyl v nhm hiroxyl. Do mt eletron dch chuyn t nhm OH v, nn nhm C=O axit cacboxylic km hot ng hn nhm C=O anehit v xeton, cn nguyn t H nhm OH axit th linh ng hn nhm OH ancol v nhm OH phenol. GV chiu bi tp 2 (SGK) ln mn hnh cho HS tho lun. 2. Hy so snh nhit nng chy, nhit si v tan trong nc ca anehit v axit tng ng. Gii thch nguyn nhn dn ti s khc nhau gia chng. HS tho lun v a ra kt qu: Anehit HCHO CH3CHO Axit cacboxylic HCOOH CH3COOH tnc <15 C
0

ts 19 C
0

tan tan tt tan tt tan

1230C tnc 8,40C 16,6 C

0

210C ts 100,70C 118,1 C

0

Nhit nng chy (tnc), nhit ca axit cao hn anehit tng ng v axit to c lin kt hiro lin phn t, cn anehit th khng. GV chiu bi tp 3 (SGK) ln mn hnh cho HS tho lun. 3. a) Hy nu nhng phn ng nhm chc axit cacboxylic, cho th d minh ha. b) Hy nu cc phn ng gc hirocacbon ca axit cacboxylic, cho th d minh ha. HS tho lun v a ra kt qu: a) Phn ng nhm chc axit cacboxylic. + Phn li thun nghch.
268

RCOOH + H2O U RCOO + H3O+ + C tnh cht ca mt axit (tc dng vi kim loi, baz, oxit baz, mui ca axit yu hn). RCOOH + NaOH RCOONa + H2O 2RCOOH + Mg (RCOO)2Mg + H2 + Phn ng vi ancol (phn ng este ho).
H 2 SO 4 ZZZ X RCOOH+ROH YZZ o Z RCOOR+ H2O t

+ Phn ng tch nc lin phn t.

P2 O5 2RCOOH (RCO)2O + H2O

b) Phn ng gc hirocacbon ca axit cacboxylic: Phn ng gc no.

P CH3CH2COOH + Cl2 CH3CHCOOH + HCl

Cl Phn ng gc thm. COOH + HNO3

H2SO4

COOH + H2 O NO2

Phn ng gc khng no. CH2=CHCOOH + Br2 CH2CHCOOH Br Br GV chiu bi tp 4 (SGK) ln mn hnh cho HS tho lun. 4. a) Hy nu nhng phng php chung iu ch axit cacboxylic. b) Hy vit phng trnh ho hc ca phn ng iu ch axit axetic trong cng nghip i t metanol, t etilen v t axetilen. Hin nay ngi ta s dng phng php no l chnh. V sao ? HS tho lun v a ra kt qu: a) Cc phng php chung iu ch axit cacboxylic. Trong phng th nghim. + Oxi ho hirocacbon, ancol bc I. + T dn xut halogen. Trong cng nghip.

269

+ Ln men gim. + Oxi ho anehit. + i t metanol. b) Phng trnh ho hc iu ch axit trong cng nghip. T metanol.
xt, t CH3COOH CH3OH + CO
o

T etilen.
xt, t CH3COOH CH2=CH2 + O2
o

T axetilen
xt, t CH3CHO CHCH + H2O o 1 xt , t CH3CHO + O2 CH3COOH 2 Hin nay ngi ta s dng ch yu l i t metanol v CO v CH3OH d iu ch v c sn trong t nhin nn gi thnh r nht. GV chiu bi tp 5 (SGK) ln mn hnh cho HS tho lun. 5. V sao axit axetic c sn xut ra nhiu hn so vi cc axit hu c khc?
o

HS tho lun v a ra kt qu: Axit axetic l nguyn liu quan trng trong ngnh cng nghip ho cht. Nguyn liu sn xut axit axetic thng dng, d kim, cng ngh sn xut n gin hn cc axit khc. GV chiu bi tp 6 (SGK) ln mn hnh cho HS tho lun. 6. Hy nhn bit cc cht trong cc cht sau: a) Ety axetat, fomalin, axit axetic v etanol. b) Cc dung dch : axetanenhit, glixerol, axit acrylic v axit axetic. HS tho lun v a ra kt qu: a) Thuc th c dng v kt qu th hin trong bng sau: CH3COOC2H5 Qu tm Trng bc Na Cht cn li Kt ta H2 bay hi HCHO CH3COOH Chuyn mu C2H5OH

270

b) Thuc th c dng v kt qu th hin trong bng sau: CH3COOC2H5 Qu tm Tch ra 2 nhm Cu(OH)2 un, Kt ta gch Dung dch xanh trong sut Nc brom mt mu HCHO CH3COOH C2H5OH

GV chiu bi tp 7 (SGK) ln mn hnh cho HS tho lun. 7. Cho nc brom vo hn hp gm phenol v axit axetic, n khi ngng mt mu nc brom th lc v thu c 33,1g kt ta trng. trung ho phn nc lc cn dng ht 248,0 ml dung dch NaOH 10.0% (D=1,11). Xc nh thnh phn trm hn hp ban u. HS tho lun v a ra kt qu: Phng trnh ho hc. OH OH Br Br + 3HBr + 3Br2 Br x mol xmol 3x mol CH3COOH + NaOH CH3COONa + H2O y mol HBr 3x mol y mol + NaOH NaBr + H2O

3x mol 33,1 248.1,11 . 10 = 0,69 (mol) x= nNaOH = = 0,1 (mol) 331 40.100 3x + y = 0,69 y = 0,39 (mol) m C6 H5OH = 94 x 0,1 = 9,4 (g), m CH3COOH = 60 x 0,39 = 23,4 (g) mhh = 9,4 + 23,4 = 32,8 (g) 9,4 x 100 = 28,66%, % m C6 H5OH = 32,8 % m CH3COOH = 100 28,66 = 71,34%. GV chiu bi tp 8 (SGK) ln mn hnh cho HS tho lun. 8. Kt qu phn tch nguyn t cho thy cht A cha 55,81% C, 7,01% H cn li
271

oxi; A l cht lng rt t tan trong nc, khng c v chua, khng lm mt mu nc brom, 1,72g A phn ng va vi 20,0ml dung dch NaOH 1,0M to thnh mt hp cht duy nht B c cng thc phn t C4H7O3Na. Khi un nng vi dung dch axit v c, t B li to thnh A. a) Xc nh cng thc phn t ca A. b) T cng thc phn t v tnh cht ca A, cho bit A thuc loi hp cht no. c) Vit cng thc cu to ca A, B v cc phng trnh ho hc nu. HS tho lun v a ra kt qu: . A: 55,81% C; 7,01% H %O = 37,18% Gi A l CxHyOz 55,81 7,01 37,18 x:y :z= : : 12 1 16 x : y : z = 4,65 : 7,01 : 2,32 = 2 : 3 : 1 A c cng thc ( C2H3O)n V A + NaOH cho hp cht duy nht B c cng thc C4H7O3Na ; B + axit v c cho tr li A ; A khng c v chua, khng lm mt mu nc brom. Suy ra A l este ni. 20.1 = 0,02 ( mol) S mol NaOH bng s mol A nA = 1000 MA = 1,72 : 0,02 = 86 (g/mol) (24 + 3 + 16) n = 86 n = 2 C4H6O2 CH2CH2 ng vi cng thc cu to: CH2O CH2 CH2 C = O + NaOH HOCH2 CH2CH2COONa CH2 O (A) Khi un vi axit v c:
4
+

C=O

(B)
3 2 1
+ o

CH2CH2 C=O CH2 O

H H ,t HOCH2CH2CH2COOH HOCH2CH2CH2COONa

Nu nhm OH v tr 2 hoc 3 th khi un vi axit v c s to ra axit khng no.

272

H ,t CH3CHCH2COOH CH3CH=CHCOOH H2 O

+ o

OH GV chiu bi tp 9 (SGK) ln mn hnh cho HS tho lun. 9. Tng hp isoamyl axetat ( lm du chui) gm ba giai on nh sau: A: Cho 60 ml axit axetic bng (axit 100%, D=1,05 g/cm3), 108,6ml 3-metybut 1ol (ancol isoamylic, D= 0,81 g/cm3, nhit si xem bng 8.3) v 1 ml H2SO4 vo bnh cu c lp my khuy, ng sinh hn (xem hnh v u chng) ri un si trong vng 8 gi. B: Sau khi ngui, lc hn hp thu c vi nc, chit b lp nc, ri lc vi dung dch Na2CO3, chit b lp dung dch nc, li lc hn hp thu c vi nc, chit b lp nc. C: Chng ct ly sn phm 1420C thu c 60,0 ml isoamyl axetat. Isoamyl axetat l cht lng D = 0,87 g/cm3, si 142,50C, c mi thm nh mi chui chn (mi du chui). a) Dng hnh v m t 3 giai on A, B, C. b) Vit phng trnh ho hc ca phn ng xy ra giai on A v B. c) Tnh hiu sut ca phn ng. HS tho lun v a ra kt qu: a) Cho axit axetic, ancol isoamylic, axit sunfuric vo bnh cu ri un si trong 8 gi. Sn phm thu c bnh tam gic. ngui, lc hn hp thu c vi nc, chit b lp nc bng phu chit loi b phn ln axit axetic v H2SO4 cn li.

Lc hn hp thu c vi dung dch Na2CO3, li chit b lp nc loi ht axit cn li. Lc hn hp thu c vi nc ln na, chit b lp nc ra vt Na2CO3 cn li. Chng ct ly sn phm 142 1430C thu c isoamyl axetat.

273

2 4 ZZZZ X b) CH3COOH + (CH3)2CHCH2CH2OH YZZZ Z H SO ,t

CH3COOCH2CH2CH(CH3)2 + H2O 2CH3COOH + Na2CO3 2CH3COONa + CO2 + H2O H2SO4 + Na2 SO4 Na2SO4 + CO2 + H2O c) Khi lng axit axetic ban u: 60.1,05 = 63 (g) Khi lng isoamylic ban u: 108,6. 0,81 = 88 g Khi lng este isoamyl axetat thu c: 60.0,87 = 52 (g) m este= 130(g) mancol = 88 (g),
H 2 SO 4 ,t ZZZZ X CH3COOH + (CH3)2CHCH2OH YZZZ Z CH3COOCH2CH2CH(CH3)2 + H2O o

60g 88g 130g Ta thy lng axit axetic d. Nu ancol isoamylic phn ng ht th phi thu c 130g este isoamyl axetat, nhng thc t ch thu c 52g. Vy hiu sut ca phn ng l: 52 H= .100% = 40% 130 Bi tp ngh
1. Cho axit hu c no, mch h c dng (C2H3O2)n. Xc nh cng thc phn t ca axit?

A. C4H6O4. C. C6H9O6.

B. C2H3O2. D. Kt qu khc.
p n A

2. Cp cht no sau y c th tn ti c trong dung dch nc?

A. CH3COOH v C6H5ONa. C. C2H5OH v C6H5ONa.

B. CH3NH2 v C6H5NH3Cl. D. C6H5OH v C2H5ONa.

p n C 3. So snh nng CM ca 2 dung dch NaOH v CH3COONa c cng pH:

A. NaOH > CH3COONa. C. NaOH = CH3COONa.

B. NaOH < CH3COONa. D. Khng so snh c.

p n B 4. t chy hon ton a mol hn hp X gm 2 mui ca hai axit no n chc l ng ng lin tip. Cn 9,52 (l) O2 (00C, 2 atm). Phn cht rn cn li sau
274

khi t cn nng 10,6 g. Xc nh CTPT ca hai mui v s mol ca chng trong hn hp X. A. CH3COONa (0,15 mol) v C2H5COONa (0,1mol). B. CH3COONa (0,1 mol) v C2H5COONa (0,15mol). C. C2H5COONa (0,05 mol) v C3H7COONa (0,15mol). D. C2H5COONa (0,1 mol) v C3H7COONa (0,1mol).
p n D 5. Cho 300ml dung dch axit axetic 1M v 50 ml ancol etylic (ru 460) c cho thm mt t H2SO4 c vo mt bnh cu v un nng bnh sau mt thi gian thu c 19,8 g este. Hiu sut phn ng este ha l: A. 65%. B. 75%. C. 85%. D. Kt qu khc. p n B 6. Cho hn hp X gm ancol etylic v hn hp 2 axit no n chc k tip nhau trong dy ng ng,tc dng ht vi Na gii phng ra 4,48 (l) H2(ktc). Mt khc nu un nng hn hp X (c H2SO4c lm xc tc) th cc cht trong hn hp X phn ng va vi nhau v to thnh 16,2 g hn hp este. CTPT ca 2 axit l: C. C3H7COOH v C4H9COOH. A. HCOOH v CH3COOH. D. C4H9COOH v C5H11COOH B. CH3COOH v C2H5COOH. p n A.

275

Bi 63

thc hnh

Tnh cht ca anehit v axit cacboxylic

A. Mc tiu bi hc 1. Kin thc

Cng c h thng ho tnh cht vt l v ha hc ca anehit v axit cacboxylic. Gip HS bit cch tin hnh mt s th nghim th tnh cht ca anehit v axit cacboxylic. Phn bit ba dung dch ring bit khng dn nhn axit fomic, fomalin, glixerol. Phn bit ba dung dch ring bit khng dn nhn axit axetic, anehit fomic, etanol.
2. K nng

Rn luyn tnh thn trng chnh xc khi tin hnh th nghim vi cc cht chy, c. S dng dng c ho cht tin hnh c an ton, thnh cng cc th nghim. Rn luyn k nng quan st, nu v gii thch hin tng. Vit tng trnh th nghim.
3. Tnh cm, thi

Thng qua hot ng th nghim to nn hng th khi hc b mn ho hc.

B. chun b ca GV v HS

GV My tnh, my chiu, cc phiu hc tp. Ho cht: + Axit axetic. + Giy qu tm. + Dung dch fomanehit. + Mu Na2CO3. + Dung dch NH3 10%. + Dung dch AgNO3 1%.
276

+ Etanol. Dng c: + ng nghim , n cn. + ng ht nh git.

+ Anehit axetic.

+ Nt cao su c lp ng thu tinh vut nhn. + B gi th nghim. HS: n tp tnh cht ca axit axetic, anehit. Xem trc bi thc hnh.
C. tin trnh dy hc Hot ng ca GV Hot ng 1 Dn d trc bui thc hnh Hot ng ca HS

GV nu cc ni dung chnh ca bui HS nghe GV trnh by v tho lun theo nhm thc hnh. thc hnh. GV yu cu HS trnh by cc ni dung kin thc lin quan n bui thc hnh. Lu HS khi dng ho cht v s dng cn thn cc dng c th nghim. Chia lp hc thnh cc nhm thc hnh mi nhm gm 45 HS.
I. Ni dung th nghim v cch tin hnh Hot ng 2 Th nghim 1. phn ng trng bc GV Lu cn ra tht sch ng HS ra ng nghim. nghim bng cch cho vo ng nghim 12 ml NaOH c un nng nh, ra nhiu ln bng nc ct. GV hng dn HS iu ch thuc th HS nhn xt: Ban u thy dung dch Tollens: Nh vo ng nghim ( ra b vn c sau dung dch trong sut sch) 1 ml dung dch AgNO3 1%, lc tr li do to phc tan:
277

ng nghim v nh t t tng git dung dch NH3 2M cho n khi kt ta AgNO3 + 3NH3 + 2H2O sinh ra b ho tan ht (thuc th [Ag(NH3)2]OH + NH4NO3 Tollens s km nhy nu cho d dung dch NH3). Yu cu HS quan st gii thch. GV hng dn HS tin hnh th HS tin hnh th nghim: nghim phn ng trng bc yu cu HS Nh t t dung dch anehitfomic 40% quan st hin tng v gii thch: vo thuc th Tollens. Khi khng un nng. Khi khng un nng. Khi un nng nh vi pht (60 Nhn xt: Khng thy c hin tng g. 700C). Khi un nng nh. GV yu cu i din tng nhm vit Nhn xt: Thy lp bc kim loi sng phng trnh ho hc, gii thch. bng nh gng bm vo thnh ng nghim. GV lu HS: i khi bc kim loi HS quan st hin tng v ghi vo v tch ra dng kt ta v nh hnh thc hnh. mu en. Gii thch v c phn ng ho hc: HCHO+ 4[Ag(NH3)2]OH (NH4)2CO3 + 4Ag + 6NH3 + 2H2O Nhn xt: HCHO l cht kh. Ag+ l cht oxi ho. GV yu cu HS gii thch ti sao HS tho lun v a ra kin. khng lc mnh ng nghim khi un Khng nn lc mnh ng nghim khi nng. un nng, lng bc to thnh bm ht trn thnh ng nghim. GV hng dn HS cch ra ng nghim HS ra cc dng c dng. cha kim loi bc bng cch cho HNO3 c vo lc nh n khi thy lp bc bm trong ng nghim tan ht sau ra li bng nc ct, ch khi ra vi HNO3 c phi ht sc cn thn.

278

Hot ng 3 Th nghim 2. Phn ng c trng ca anehit v axit cacboxylic

GV hng dn HS phn tch th HS tho lun v phn tch th nghim. nghim nhn bit ba ng nghim mt nhn cha cc dung dch: axit axetic, anehit axetic, etanol. Nu tnh cht ho hc c trng ca Anehit c phn ng trng bc c anehit, tnh cht no c th dng trng c th dng nhn bit. nhn bit c anehit. Axit cacboxylic c nhiu tnh cht Nu tnh cht ho hc c trng ca nhng tnh cht lm giy qu l c axit cacboxylic, tnh cht no c th trng c th dng nhn bit axit. dng nhn bit c axit axetic. S dng nhn bit: Yu cu HS nu s nhn bit. C2H5OH, CH3CHO, CH3COOH
+ qu tm

khng c hin tng qu tm ho hng C2H5OH, CH3CHO CH3COOH

+ [Ag(NH3)2]OH khng c kt ta xut hin Ag C2H5OH CH3CHO

GV yu cu HS tin hnh cc th nghim HS tin hnh th nghim: kim tra s c th nhn bit c iu ch mt lng nh thuc th cc cht hay khng? Tollens t dung dch AgNO3 v dung dch NH3 trong ng nghim. Dng giy qu tm nhn ra CH3COOH. Dng thuc th tollens nhn ra

279

anehit axetic (phn ng trng bc). GV b sung: C th nhn ra anehit Cn li l etanol. trc bng phn ng trng bc, sau nhn ra axit axetic bng qu tm.
Hot ng 4 II. Cng vic sau bui thc hnh

GV nhn xt v bui thc hnh v HS thu dn, v sinh phng th nghim hng dn HS thu dn ho cht, ra cn thn, an ton. ng nghim v dng c th nghim, v sinh phng th nghim. GV yu cu HS lm tng trnh theo mu.

HS lm tng trnh theo mu sau y: Ngy thng.nm. H v tn: Lp:. T th nghim:. Tng trnh ho hc bi s:. Tn bi:

Tn th nghim

Phng php tin hnh

Hin tng quan st

Gii thch vit phng trnh phn ng

280

n tp cui nm
A. Mc tiu bi hc 1. Kin thc n tp h thng ho kin thc v:

S in li, khi nim axitbaz, pH ca dung dch v phn ng trao i ion trong dung dch in li. Nhng tnh cht ho hc c bn ca nhm nit, nhm cacbon, cc n cht v hp cht ca nit, photpho, cacbon, silic. Bit cc phng php iu ch, ng dng ca cc n cht v hp cht ca chng. Cc khi nim: Cht hu c, cng thc v cu trc phn t, danh php cc hp cht hu c, cc loi phn ng hu c c bn, s lc v c ch phn ng (phn ng th, phn ng cng, phn ng tch, ), ng ng, ng phn cu to v ng phn lp th. Hiu c mi quan h gia cu to ca hp cht hu c vi nhng tnh cht vt l, tnh cht ho hc ca hp cht hu c. Hiu c nhng tnh cht vt l, tnh cht ho hc, bit nhng ng dng v phng php iu ch cc loi hp cht hu c trong chng trnh ho hc lp 11.
2. K nng

Bit lp k hoch gii mt bi ton ho hc. Bit vn dng l thuyt ho hc gii quyt mt s vn n gin trong i sng, trong sn xut. Bit lm vic vi cc ti liu tham kho, ti liu gio khoa nh: Tm tt ni dung, phn tch ni dung, kt lun vn .
3. Tnh cm, thi

To s hng th, ham thch hc tp b mn ho hc thng qua hot ng gii bi tp, luyn tp.

281

B. chun b ca GV v HS

GV: My tnh, my chiu, h thng bi tp v cc cu hi gi . HS: n tp cc kin thc thng qua hot ng gii bi tp.

C. tin trnh dy hc GV t chc cc nhm HS tho lun cc ni dung cn n tp lp 11 di dng cc bi tp trc nghim khch quan(2). Hot ng 1 s in li 1. C mt dung dch cht in li yu. Khi thay i nng dung dch (nhit khng i) th:

A. in li v hng s in li u thay i. B. in li thay i v hng s in li khng thay i. C. in li khng thay i v hng s in li thay i. D. in li v hng s in li u khng thay i.
p n B 2. Cht phi thm vo dung dch lm pH thay i t 12 xung 10 l:

A. Nc ct C. Hiroclorua

B. Natri hiroxit D. Natri axetat

p n C

3. Dung dch HNO3 c pH = 2. Cn pha long dung dch trn bao nhiu ln thu c dung dch c pH = 3?

A. 1,5 ln.

B. 20 ln.
+

C.
2+

15 ln.

2 4

D. 10 ln.
p n D

4. Mt dung dch cha cc ion: Na , Mg , Cl , SO . Trong dung dch tn ti

bao nhiu phn t? A. 2 B. 3 C. 4 D. Khng tn ti phn t no.

p n D

(2) Xem thm: Cao C Gic. Cc dng thi trc nghim ho hc - Nxb Gio dc, 2007.

282

5. Cho dung dch cha x mol Ca(HCO3)2 vo dung dch cha x mol Ca(HSO4)2 th kt lun no sau y ng?

A. Khng c hin tng g. B. C hin tng si bt kh. C. C hin tng si bt kh v dung dch b vn c. D. Dung dch sau phn ng c pH < 7.
p n C 6. Cp cc dung dch no sau y c xp theo chiu tng dn v pH. A. H2S, NaCl, HNO3, KOH.

B. C. D.

HNO3, H2S, NaCl, KOH. KOH, NaCl, H2S, HNO3. HNO3, KOH, NaCl, H2S.
p n B
2+ 2+

7. Trong mt dung dch c cha a mol Ca ; b mol Mg . Nu a = 0,01 ; c = 0,01 ; d = 0,03 th NO 3

; c mol Cl v d mol

A. b = 0,02 C. b = 0,01

B. b = 0,03 D. b = 0,04
p n C

8. Dy cc mui u thy phn khi tan trong nc l: A. Na3PO4, Ba(NO3)2, KCl, KHSO4, AlCl3.

B. C.

Ba(NO3)2, Mg(NO3)2, NaNO3, KHS, Na3PO4. KHS, KHSO4, K2S, KNO3, CH3COONa.
p n D

D. AlCl3, Na3PO4, K2SO3, CH3COONa, Fe(NO3)3.

9. Trn 50 ml dd Ba(OH)2 pH=13 v 50ml dd H2SO4 0,04M

a) pH ca dung dch to thnh l: A. 13 B. 3 b) Lng kt ta to ra l: A. 0,932g B. 0,466g

C. 2

D. Kt qu khc
p n D

C. 1,165g

D. Kt qu khc
p n B
283

10. Dung dch NH3 gm:

A. Phn t NH3 C. ion OH

B. ion NH4+ D. A, B, C ng.

p n D 11. Hin tng no xy ra khi trn dung dch NH4Cl vi dung dch NaAlO2 v un nh? a. Khng c hin tng g xy ra. b. Ban u c kt ta keo trng sau tan. c. C kh mi khai bay ra. d. Va c kt ta keo trng khng tan, va c kh mi khai bay ra. p n D 12. Cht trung tnh l cht: a. Va th hin tnh axit va th hin tnh baz. b. Khng th hin tnh axit v c tnh baz. c. Ch th hin tnh axit khi gp baz mnh. d. Ch th hin tnh baz khi gp axit mnh. p n B 13. Cn trn theo t l no v khi lng 2 dung dch NaCl 45% v NaCl 15% c dung dch NaCl 20%? a. 1 :3. c. 2 : 5. b. 1 : 5. d. 2 :3. p n B 14. Mt cht lng khng mu c cc tnh cht sau:

Lm cho phenolphtalein mu hng tr li khng mu. Tc dng vi mui cacbonat gii phng CO2. Cht lng l: A. Dung dch NaOH. C. Dung dch FeCl3. B. Dung dch NaCl. D. Dung dch Ba(NO3)2.

p n C 15. Hin tng no sau y xy ra khi cho t t dung dch kim vo dung dch ZnSO4 cho n d? a. Xut hin kt ta trng khng tan.
284

b. Xut hin kt ta trng sau tan ht. c. Xut hin kt ta xanh sau tan ht. d. C kh mi xc bay ra. p n B Hot ng 2 nit photpho 1. Khi iu ch N2 t dung dch NaNO2 v NH3 bo ho ngi ta tin hnh un bnh cu nh th no? a. Ban u un mnh, sau gim dn. b. un mnh t u cho n khi kt thc. c. Ban u un nh, sau tng dn. d. Ban u un nh, c bt kh thot ra th ngng un. p n D 2. Khi lm th nghim vi P trng cn phi: a. Cm bng tay c eo gng. b. Dng cp gp nhanh mu P ra khi l v cho ngay vo chu ng y H2O khi cha s dng. c. Trnh cho tip xc vi H2O. d. ngoi khng kh. p n B 3. C th phn bit mui amoni vi cc mui khc bng cch cho tc dng vi kim mnh v khi ng nghim ng mui amoni: a. Chuyn thnh mu . b. Thot ra cht kh khng mu c mi xc c trng. c. Thot ra cht kh mu nu. d. Thot ra cht kh khng mu, khng mi. p n B 4. Theo dy:

HNO3 HPO3 HAsO3, tnh axit:

b. Lc u tng, sau gim. d. Gim dn. p n D
285

a. Khng thay i. c. Tng dn.

5. Trong phn ng: 3NO2 + H2O 2HNO3 + NO, NO2 ng vai tr g? a. Cht oxi ho. c. Cht t oxi ho kh.

b. Cht kh. d. Khng l cht oxi ho, kh. p n C

6. pht hin ion NO3 trong dung dch mui, ngi ta s dng thuc th: a. Kim loi Ag v Cu. c. Dung dch H2SO4 long v Cu. b. Dung dch NH3. d. Kim loi Ag v FeCl2.

p n C 7. Mt hc sinh trong khi lm th nghim, do bt cn lm mt t dung dch NH3 ra sn nh. S dng cht no sau y x l sn nh? a. Xa. c. Mui n. b. Gim n. d. X phng. p n B 8. Hm lng m (%N) trong loi m no sau y l ln nht? a. Amoni nitrat. c. Ur. b. Amoni sunfat. d. Canxi nitrat.

p n C 9. Ho tan hon ton 13,92 gam Fe3O4 bng dung dch HNO3 thu c 448 ml kh NxOy (ktc). Xc nh NxOy? a. NO. b. N2O. c. NO2. d . N 2O 5. p n A 10. Phng php no sau y dng thu c NH3 trong phng th nghim: a. Thu kh NH3 bng phng php y nc. b. Thu kh NH3 bng phng php y khng kh ra khi bnh thu nga. c. Thu kh NH3 bng phng php y khng kh ra khi bnh thu p ngc. d. C 3 cch u c. p n C 11. S iu ch HNO3 no sau y dng iu ch HNO3 trong cng nghip? a. N2 NH3 NO HNO3. b. N2 Ca3N2 NH3 NO NO2 HNO3. c. N2 NO NO2 KNO3 HNO3.
286

d. N2 NO HNO2 HNO3. p n A 12. Phot pho c la chn sn xut dim an ton thay cho photpho trng v l do no sau y? a. Photpho khng c hi i vi con ngi b. Photpho khng d gy ho hon nh photpho trng. c. Phot pho trng l ho cht c hi. d. C a, b, c. p n D 13. Cng thc ho hc ca supephotphat kp l: a. Ca3(PO4)2. c. CaHPO4. b. Ca(H2PO4)2. d. Ca(H2PO4)2 v CaSO4.

p n B 14. Kh nit tng i bn v mt ho hc nhit thng l do nguyn nhn no sau y? a. Phn t nit c lin kt cng ho tr khng phn cc. b. Phn t nit c lin kt ion. c. Phn t nit c lin kt ba rt bn. d. Nit c m in ln nht trong nhm VA. p n C 15. Phn ng ca NH3 vi Cl2 to ra khi trng, cht ny c cng thc ho hc l: a. HCl. c. NH4Cl. b . N2 . d. NH3. p n C Hot ng 3 Cacbon silic 1. Kh CO2 thi ra nhiu c nh hng ti mi trng v: a. Rt c. c. Gy ma axit. b. To bi cho mi trng. d. Gy hiu ng nh knh. p n D

287

2. Cho vo ng nghim 1 n 2 ml dung dch Na2SiO3 c. Sc kh CO2 vo tn y ng nghim thy kt ta H2SiO3 xut hin: a. Dng keo. c. Dng v nh hnh. b. Dng tinh th. d. Dng lng khng tan. p n A 3. thu c CO2 tinh khit t phn ng CaCO3 vi dung dch HCl, ngi ta cho sn phm kh i qua ln lt cc bnh no sau y? a. NaOH v H2SO4 c. c. H2SO4 c v NaHCO3. b. NaHCO3 v H2SO4 c. d. H2SO4 c v NaOH. p n B 4. Cng nghip silicat l ngnh cng nghip ch bin cc hp cht ca silic. Ngnh sn xut no sau y khng thuc v cng nghip silicat? a. Sn xut gm (gch, ngi, snh, s). b. Sn xut xi mng. c. Sn xut thu tinh. d. Sn xut thu tinh hu c. p n D 5. Hiu ng nh knh l hin tng Tri t ang nng ln, do cc bc x c bc sng di trong vng hng ngoi b gi li, m khng bc x ra ngoi v tr. Cht no sau y l nguyn nhn chnh gy ra hiu ng nh knh? a. NO. c. CO2. b . N2 . d. SO3. p n C 6. Kim cng v than ch l cc dng th hnh ca nguyn t cacbon. Kim cng cng nht trong t nhin, trong khi than ch mm n mc c th dng lm bt ch. iu gii thch no sau y l ng? a. Kim cng c cu trc tinh th dng t din u, than ch c cu trc lp, trong khong cch gia cc lp kh ln. b. Kim cng c lin kt cng ho tr bn, than ch th khng. c. t chy kim cng hay than ch nhit cao u to ra kh CO2. d. Mt nguyn nhn khc. p n A
288

7. iu khng nh no sau y l sai khi ni v CO2? a. Cht kh khng mu, khng mi, nng hn khng kh. b. Cht kh ch yu gy ra hiu ng nh knh. c. Cht kh khng c, nhng khng duy tr s sng. d. Cht kh dng cha chy, nht l cc m chy kim loi. p n D 8. Khi s dng ng c iezen pht in, ti sao khng nn trong phng ng kn cc ca? A. V n tiu th nhiu O2, sinh ra kh CO2 l mt cht kh c. B. V n tiu th nhiu O2, sinh ra kh CO l mt cht kh c.

C. Nhiu hirocacbon cha chy ht l nhng kh c. D. Sinh ra kh SO2.

p n B 9. Xt cc mui cacbonat, nhn nh no sau y l ng?

A. Tt c cc mui cacbonat u tan trong nc. B. Tt c cc mui cacbonat u b nhit phn to ra oxit kim loi v cacbon ioxit. C. Tt c cc mui cacbonat u b nhit phn, tr mui cacbonat ca kim loi kim. D. Tt c cc mui cacbonat u khng tan trong nc. p n C 10. Hin tng g xy ra khi trn dung dch Na2CO3 vi dung dch FeCl3? A. Xut hin kt ta mu nu. B. C cc bt kh thot ra khi dung dch. C. Xut hin kt ta mu lc nht. D. C A, B.
p n D 11. Mt cc thu tinh ng khong 20 ml nc ct. Cho 1 mu giy qu tm vo cc nc, mu tm khng thay i, sc kh cacbon ioxit vo cc nc, mu giy chuyn sang mu hng. un nng cc nc, sau mt thi gian mu qu li chuyn thnh mu tm. Gii thch no sau y l ng?

A. Nc ct c pH = 7. B. Dung dch axit H2CO3 c pH < 7.

289

C. Axit H2CO3 khng bn, un nng phn hu thnh CO2 v nc. D. C A, B, C.

p n D 12. Nhng kim loi no sau y c th iu ch c t oxit bng phng php nhit luyn nh cht kh CO? A. Fe, Al, Cu. B. Mg, Zn, Fe. C. Fe, Mn, Ni. D. Cu, Cr, Ca. p n C 13. Thi mt lung kh CO qua ng s ng m gam hn hp gm Al2O3, MgO, Fe2O3, FeO, CuO nung nng. Kh thot ra c sc vo nc vi trong thu c 15 gam kt ta trng. Sau phn ng, cht rn trong ng s c khi lng 200 gam. Tnh m?

A. 202,4 gam. C. 219,8 gam.

B. 217,4 gam. D. Kt qu khc.

p n A 14. Nung 100 gam hn hp gm NaCO3 v NaHCO3 cho n khi khi lng hn hp khng i thu c 69 gam cht rn. Xc nh % khi lng mi cht trong hn hp mui ban u? B. 16% NaHCO3 v 84% Na2CO3. A. 84% NaHCO3 v 16% Na2CO3. D. 75% NaHCO3 v 25% Na2CO3. C. 25% NaHCO3 v 75% Na2CO3. p n A 15. u l phn ng sai trong cc phn ng sau?

A. 3CO + Fe2O3 3CO2 + 2Fe B. CO + Cl2 COCl2 C. 3CO + Al2O3 2Al + 3CO2 D. 2CO + O2 2CO2
p n C Hot ng 4 i cng v ho hc hu c 1. Pht biu no sau y cha chnh xc?

A. Tnh cht ca cc cht ph thuc vo thnh phn phn t v cu to ho hc. B. Cc cht l ng phn ca nhau th c cng cng thc phn t.
290

C. Cc cht c cng klhi lng phn t l ng phn ca nhau. D. S xen ph trc to thnh lin kt , s xen ph bn to thnh lin kt . p n C. 2. S ng phn cu to ca C4H10 v C4H9Cl ln lt l: A. 2 v 2 B. 2 v 3 C. 2 v 4 D. 3 v 4. p n C. 3. Phn t no sau y c cc nguyn t cacbon nm trn cng ng thng? A. Propan B. n-butan C. Propen D. Propin. p n D. 4. t chy a gam hirocacbon X thu c 1,12 lt CO2(ktc) v 0,9 gam H2O. Mt khc a gam X c cng th tch vi 0,28 g N2(cng iu kin t0, P). Xc nh a: A. 0,72g B. 0,560g C. 0,70g D. Kt qu khc. p n C
5. Hai cht ng phn khc nhau v: A. S nguyn t cacbon B. S nguyn t hiro C. Cng thc cu to D. Cng thc phn t p n C 6. C bao nhiu ng phn amin ng vi cng thc phn t C3H9N? A. 2. B. 3. C. 4. D. 5. p n C 7. Mt hirocacbon cha bit, tm thy cacbon chim 88,9%. Cho bit u l cng thc n gin nht ca cht trong cc cht sau: B. C2H4 A. CH4 D. C2H3 C. C4H6 p n D 8. Cht X c cng thc phn t C6H10O4. Cng thc no sau y l cng thc n gin nht ca X? A. C6H10O4 B. C3H5O2 D. C12H20O8 C. C3H10O2 p n B
291

9. Kt lun no sau y l ng?

A. Phn ng ca cc cht hu c thng xy ra rt nhanh. B. Phn ng ca cc cht hu c thng xy ra rt chm v theo nhiu hng khc nhau. C. Phn ng ca cc cht hu c thng xy ra rt chm v ch theo mt hng xc nh. D. Phn ng ca cc cht hu c thng xy ra rt nhanh v khng theo mt hng nht nh.
p n B 10. Cht c mch h no sau y trong phn t ch c lin kt n?

A. C4H10 C. C6H6

B. C4H6 D. CH3COOH
p n A

11. Hp cht A c cng thc n gin nht l CH3O v c t khi hi so vi H2 bng 31,0. Cng thc phn t no sau y ng vi hp cht A ?

A. CH3O C. C3H6O3

B. C2H6O2 D. C2H6O
p n B

12. Cho cc cht sau y: CaC2 (1), CO2 (2), C2H6 (3), C2H4O2 (4), CaCO3 (5), Al4C3 (6), CO(NH2) (7), CH3OH (8), C6H12O6 (9). Cc cht hu c l

A. 1, 2, 7, 8, 9 C. 1, 2, 3, 9

B. 3, 4, 8, 9 D. 3, 4, 7, 8, 9
p n B

13. t chy hon ton hn hp hai hirocacbon l ng ng thu c 7,84 lt CO2(ktc) v 8,1 gam H2O. Tng s mol hai hirocacbon em t l:

A. 0,10 C. 0,20

B. 0,05 D. 0,15
p n A

14. Tng s ng phn cu to ca C6H12 khi hiro ho thu c isohexan l:

A. 4. C. 6.

B. 5. D. Kt qu khc.
p n B

292

15. t chy hon ton 2,3 g mt hp cht hu c X cn V (lt) O2 (ktc). Sn phm chy cho hp th ht vo bnh ng dung dch nc vi trong d. Thy c 10 gam kt ta xut hin v khi lng bnh ng dung dch nc vi tng 7,1 g. Gi tr ca V l:

A. 3,92 (l). C. 4,48 (l).

B. 3,36 (l). D.Kt qu khc.

p n B Hot ng 5 hirocacbon no

1. Hp cht sau c tn gi theo IUPAC

CH3CH2CH CH CH2CH3 CH2 CH2 CH3 CH3 B. 3,4-imetylhexan. D. 3-metyl-4-etylpentan

A. 2-etyl-3-metylpentan. C. 2,3-ietylbutan.

p n B 2. T cht no di y c th iu ch c isobutan qua phn ng hiro ho c xc tc: A. but-1-en. B. 2-metylpropen. C. but-2-en. D. but-2-in. p n B 3. Cho chui phn ng sau:
NaOH / ancol HBr,peoxit Na CH3 CH2CH2Br A B C.

A, B, C ln lt l: A. A- propanol; B- 1-brompropan; C - hexan. B. A- propen; B- 2- brompropan; C- 2,4-imetylbutan. C. A- propen; B- 1- brompropan; C- hexan. D. A- propin; B- 1,2- ibrompropan; C-1,2- imetylxiclobutan
p n C 4. Mt hirocacbon mch h (A) th kh iu kin thng, nng hn khng kh v khng lm lm mt mu nc brom. A l cht no sau y bit A ch cho mt sn phm th monoclo.

A. CH4

B. C2H6
293

C. iso-C4H10

D. tert- C5H12.
p n D

5. cng iu kin, khi t 0,1 lt C3H8 th th tch CO2 sinh ra l bao nhiu?

A. 0,3 lt C. 6,72 lt

B. 0,4 lt D. 8,96 lt

p n A 6. t chy hon ton mt hirocacbon mch h X bng lng oxi va . Sn phm kh v hi c dn qua bnh ng H2SO4 c th th tch gim hn mt na. X thuc dy ng ng no? A. Ankan B. Anken C. Ankin D. Khng xc nh c. p n A n CO2 7. t chy mt ankan th t l T = c gi tr trong khong no? n H2O

A. 0,5 T 1 C. 0,5 T <1

B. 0,5 < T <1 D. 0,5 < T 1

p n C 8. Khi t chy mt ankan trong kh clo sinh ra mt cht mui en v mt cht kh lm giy qu m. Vy sn phm ca phn ng l:

A. CnH2n+1Cl v HCl C. CCl4 v HCl

B. C v HCl D. CnH2nCl2 v HCl

p n B 9. Hp cht 2,3-imetylbutan khi phn ng vi clo theo t l mol1:1 c chiu sng thu c s sn phm ng phn l: A. 4 B. 3

C. 2

D. 1

p n C 10. Crackinh 5,8 gam butan thu c hn hp cc kh A t chy hon ton hn hp A th khi lng nc thu c l: A. 4,5 gam B. 9,0 gam

C. 10,8 gam

D. 18,0 gam
p n B

294

11. Xc nh sn phm chnh ca phn ng sau:

as CH3 CH CH2 CH3 + Cl2 1:1

CH3 A. CH3 CHCHCH3 CH3Cl B. CH3 CClCH2CH3 CH3

12. Cho cc cht sau.

C. (CH3)2CHCH2CH2Cl D. CH2ClCHCH2CH3. CH3

p n B

C2H6 (I)

C 3H 8 (II)

nC4H10 (III)

iC4H10 (IV)

Nhit si tng dn theo dy: A. (III) < (IV) < (II) < (I). C. (III) < (IV) < (II) < (I).

B. (I) < (II) < (IV) < (III). D. (I) < (II) < (III) < (IV).

p n B 13. Oxi ho hon ton 0,1mol hn hp X gm 2 ankan. Sn phm thu c cho i qua bnh 1 ng H2SO4 c, bnh 2 ng dung dch Ba(OH)2 d th khi lng ca bnh 1 tng 6,3g v bnh 2 c m gam kt ta xt hin. Gi tr ca m l:

A . 68,95g. C. 49,25g.

B. 59,1g. D. Kt qu khc.
p n B

14. Tn gi ca cht hu c X c CTCT :

CH3

A. 1-metyl-5-etylxyclohexan. B. 5-etyl-1-metylxyclohexan.

C 2H 5 C. 1-metyl-3-metylxyclohexan. D. 3-etyl-1-metylxyclohexan.
p n A

15. Tn gi cu cht hu c X c CTCT :

CH3CH2 CH CHCH3 Cl NO2

295

A. 3-clo-2-nitropentan. B. 2-nitro-3-clopetan.

C. 3-clo-4-nitropentan. D. 4-nitro-3-clopentan.
p n A Hot ng 6

hirocacbon khng no
H 2SO 4 1. Cho phn ng: Propin + H2O A. H+

Vy A l cht no di y?

A. CH2 = C(CH3) OH. C. CH3COCH3.

B. CH2 = CH CH2OH. D. CH3CH2CHO

p n C

2. Anken thch hp iu ch 3- etylpentan-3- ol bng phn ng hirat ho l:

A. 3-etylpent-1-en. C. 3-etylpent-3-en.

B. 3-etylpent-2-en. D. 3,3-ietylpent-2-en.
p n B

3. Khi cho C2H4 li qua dung dch KMnO4 long, ngui th sn phm hu c no c to thnh?

A. HOCH2CH2OH. C. HOOCCOOH.

B. HOCCHO. D. KOOCCOOK.
p n A

4. Cht no sau y khng phn ng c vi dung dch AgNO3/ NH3?

A. CH3 C CH. C. HCl.

B. CH3CHO. D. (CH3)2CO.
p n D

5. Nguyn nhn xut hin ng hnh hc anken l:

A. Do phn t anken c cha c lin kt i v lin kt n. B. Do s cng nhc ca lin kt trong hp cht anken, mt khc nguyn t cacbon mang ni i c cc nguyn t, nhm nguyn t khc nhau lin kt vi chng. C. Do s linh ng ca lin kt trong ni i C= C. D. kin khc.
p n B
296

6. CHCH + KMnO4 + H2O H2C2O4 + MnO2 + KOH.

H s cn bng ca phn ng trn l. A. 3, 8, 6, 3, 8, 4. B. 3, 8, 8, 3, 6, 8. C. 3, 8, 2, 3, 8, 8. D. 3, 8, 4, 3, 8, 8.

p n D 7. nh ngha no sau y l ng: Ankaien l hp cht:

A. C cu to gm hai lin kt i. B. Hirocacbon mch h c hai lin kt i lin hp. C. Hirocacbon mch h c hai lin kt i trong phn t. D. Hirocacbon c cng thc chung l CnH2n2
p n C 8. u l sn phm ca phn ng gia axetilen vi NH4Cl/ CuCl ?

A. CH2 =CHCH=CH2 C. CH CCCH

B. CH2 = CHCCH D. C A, B, C.
p n B

9. Sn phm no sau y c s dng lm nhin liu cho n x?

A. C2H6. C. C2H2.

B. C2H4 D. C A, B, C.

p n C 10. Mt polime c khi lng phn t 108000 vc do 2000 mt xch lin kt vi nhau. Bit polime ch c hai nguyn t l C v H, vy monome to ra polime l? A. Propilen B. Stiren C. Buta-1,3-ien D. Etilen p n C 11. Hn hp X gm 3 kh C2H4 ,C2H6 ,C2H2 tinh ch C2H6 ngi ta cho X ln lt li chm qua cc dung dch: B. Dung dch AgNO3/NH3, dung dch Br2 A. Dung dch KMnO4.

C. Dung dch Br2.

D. C A, B, C.
p n C

12. Dn 8,1(g) hn hp kh X gm (CH3CH2CCH, CH3CCCH3) li qua bnh ng dung dch Br2 d thy c m gam brom phn ng. Gi tr ca m l: A. 16g. B. 32g.
297

C. 48g.
13. Tn gi ca hp cht sau l:

D. Kt qu khc.
p n C

CH3CH=C C CH CH3 A. 2-metylhex-4-in-2-en. B. 2-metylhex-2-en-4in. C. 4-metylhex-3-en-1-in. D. 3-metylhex-1-in-3-en.

p n D 14. t chy hon ton 0,1mol hn hp gm CH4, C4H10 v C2H4 thu c 0,14 mol CO2 v 0,23 mol H2O. S mol ca ankan c trong hn hp l:

A. 0,03mol C. 0,045mol

B. 0,06mol D. 0,09mol
p n D

15. Trong s cc phn t sau y phn t no nm trn 1 mt phng:

A. CH4 C. C2H6

B. C2H4 D. C6H12
p n B Hot ng 7

hirocacbon thm, ngun hirocacbon thin nhin 1. Trong phn ng ankyl ho benzen di y c th nhn sn phm l cht no?
AlCl3 ,t C6H6 + R Cl ?
0

A. Monoankylbenzen. C. Triankylbenzen.

B. iankylbenzen. D. C A, B, C.
p n D

2. Cc cp cht sau c quan h vi nhau nh th no?

(1) C6H6 v C6H5CH3

(2) C6H6 v C6H5NO2

(3) o- CH3C6H4CH3 v m- CH3C6H4CH3 A. 1- ng ng; 2- ng phn; 3- dn xut. B. 1- ng ng; 2- dn xut; 3- ng phn.

298

C. 1- ng phn; 2- ng ng; 3- dn xut. D. 1- dn xut; 2- ng ng; 3- ng phn.

p n B 3. Hp cht thm A c cng thc phn t l C8H10. Cho A tc dng vi dung dch KMnO4 to ra mt axit c cu to i xng. A c tn gi nh th no?

A. Etylbenzen. C. m- metyltoluen.

B. o- metyltoluen. D. p- metyltoluen.
p n D

4. Clo ho toluen bng clo c mt nh sng thu c sn phm no di y? a. Benzyl clorua. c. m- clotoluen. b. o- clotoluen. d. p- clotoluen p n A 5. Sn phm chnh ca phn ng hiro ho benzen bng H2, xc tc Ni di p sut 10 atm, 15000C l cht no sau y? a. Xiclohexa-1,3-ien. c. Xiclohexan. b. Xiclohexen. d. Hexan. p n C 6. iu ch m-clonitrobenzen t benzen ta thc hin nh sau:

A. Halogen ho benzen ri nitro ho sn phm . B. Nitro ho benzen ri clo ho sn phm. C. Nitro ho benzen ri hiro ho sn phm. D. Clo ho benzen ri nitro ho sn phm.
p n B 7. Thuc th no sau y c th dng nhn bit benzen, toluen, stiren ng trong ba bnh mt nhn. a. Dung dch brom c. Dung dch KMnO4 b. Dung dch AgNO3/NH3 d. Dung dch HNO3 p n C

299

8. Hidrocacbon X th lng c phn trm khi lng H xp x 7,7%. X tc dng c vi dung dch brom. Cht no sau y l cng thc phn t ca cht X? a. Axetilen c. Benzen b. Vinylaxetilen d. Stiren p n D 9. Thnh phn chnh ca kh thin nhin l: a. CO c. C 2 H 6 b. H 2 d. CH4 p n D 10. Trong sn phm thu c khi chng ct than c hp cht hirocacbon A l cht rn d bay hi, t khi ca A so vi oxi bng 4, A khng lm mt mu dung dch nc Br2 nhng c th tham gia phn ng cng H2 to thnh hp cht no A l:

A. Toluen C. Naphtalen

B. Etylbenzen D. Stiren
p n C

11. Mt hirocacbon A c CTPT l C8H10. A c bao nhiu ng phn bit A c cha vng benzen?

A. 3

B. 6

C. 5

D. 4
p n D

12. phn bit 4 cht lng: benzen, toluen, stiren, etylbenzen ngi ta dng thuc th no sau y:

A. Dung dch Br2. C. Dung dch HNO3c.

13. Pht biu no sau y ng?

B. Dung dch KMnO4. D. Dung dch NaOH.

p n B

A. Toluen phn ng vi HNO3 c (trong H2SO4 c) d hn benzen. B. Benzen d phn ng vi brom hn phenol. C. Etilen d phn ng vi dung dch brom hn vinyl clorua. D. But-1-en phn ng cng HI d hn but-2-en.
p n A.
300

Hot ng 8 dn xut halogenancol phenol 1. Sp xp cc cht sau theo th t nhit si tng dn:

1) butan
a. 1 < 2 < 3 < 4. c. 1 < 4 < 2 < 3

2) metanol

3) etanol

4) nc.

B. 1 < 3 < 2 < 4

d. 2 < 3 < 4 < 1.

p n A 2. Trong cng nghip, phenol c iu ch bng phng php no sau y? a. T nguyn liu ban u l benzen iu ch ra phenol. b. Nha than cho tc dng vi dung dch kim ri sc CO2 vo dung dch tch ly phenol. c. Tin hnh oxi ho cumen thu sn phm l phenol. d. C a, b, c. p n C 3. Cho ancol A: (CH3)2CHCH2CHOHCH3. Gi tn theo danh php IUPAC? a. 2- metylpetan-4-ol. c. 4- metylpetan-2-ol. b. 2- metylpetan-4-on. d. 4- metylpetan-2-on.

p n C 4. nhn bit 3 cht: phenol, stiren, ancol benzylic, c th ch dng duy nht mt ha cht no trong s cc cht sau lm thuc th: a. Na kim loi c. Dung dch Br2 b. Dung dch NaOH d. Dung dch HCl. p n C 5. iu kin no thc hin phn ng sau?
? C6H5Cl + 2NaOH C6H5ONa + NaCl + H2O.

a. NaOH long/ t0. c. NaOH/ C2H5OH, t0.

b. NaOH c/ t0 cao, p cao. d. nh sng. p n B

6. un nng mt ancol no, n chc X vi axit H2SO4 c thu c hp cht hu c Y c dX/Y = 1,321. Xc nh X? a. CH3OH. b. C2H5OH.
301

c. C3H7OH.

d. C4H9OH. p n D
0

7. un 132,8 (g) hn hp 3 ancol no, n chc vi H2SO4 c 140 C thu c 111,2 (g) hn hp cc ete (c s mol bng nhau). Tnh s mol mi ete? a. 0,1 mol. c. 0,3 mol. b. 0,2 mol. d. 0,4 mol. p n B 8. Xc nh s ng phn cu to ca cc ancol c cng CTPT l C4H10O.

a. 2

B. 3

C. 4

D. 5.
p n C

9. C th thu c ti a bao nhiu sn phm anken khi tch nc t ancol

3- metylbutan- 2- ol?
a. 1. b. 2. c. 3. d. 4. p n B 10. Trong cng nghip, phenol c iu ch bng phng php no sau y? a. T nguyn liu ban u l benzen iu ch ra phenol. b. Nha than cho tc dng vi dung dch kim ri sc CO2 vo dung dch tch ly phenol. c. Tin hnh oxi ho cumen thu sn phm l phenol. d. C A, B, C. p n C 11. Cho s :
H2 SO4 Br2 KOH / ancol (A) (C) Cao subuna C4H9OH (B) o o t >170

CH3 B. CH3COH CH3 C. CH3CH2CHOHCH3 D. C 3 u c. p n C 12. Kh nng tham gia phn ng este ho vi axit hu c ca Ancol theo th t: A. Ancol bc I > Ancol bc II > Ancol bc III. B. Ancol bc II > Ancol bc III > Ancol bc I.
302

CTCT ph hp ca C4H9OH l : A. CH3CH2CH2CH2OH

C. Ancol bc III >Ancol bc II > Ancol bc I. D. Ancol bc II > Ancol bc I > Ancol bc III.
p n A 13.

C4H8Cl2 (A) Dung dch mu xanh lam.

NaOHd

CTPT ph hp ca C4H8Cl2 l: B. CH3CH2CHClCH2Cl. A. CH2ClCH2CH2CH2Cl. D. CH3CH(CH2Cl)2. C. CH3CHClCH2CH2Cl.

p n B 14. Xc nh cng thc cu to ng ca C4H9OH bit khi tch nc iu kin thch hp thu c 3 anken : A. Ancol butylic . B. Ancol tert-butylic. C. Ancol sec-butylic. D. Khng th xc nh . p n C 15. Cho cc cht sau : p-NO2C6H4OH (1) m-NO2C6H4OH (2) o-NO2C6H4OH(3) Tnh axit tng dn theo dy : A.(1)<(2)<(3). B.(1)<(3)<(2). C.(3)<(1)<(2). D.(2)<(3)<(1). p n D Hot ng 9 anehitxetonaxit cacboxylic 1. Cng thc tng qut CnH2nO c th l:

A. Ancol khng no. C. Anehit no.

2. Cho phn ng:

B. Ete khng no. D. C A, B, C.

p n D

CH2 = CH CHO + HBr ? B. CH2BrCH2CHO. D. CH3CHBrCHBr OH.

p n B

Chn sn phm chnh: A. CH3CHBr CHO C. CH2 =CH CHBr OH

3. Cho anehit mch h A. Tin hnh hai th nghim:

303

Th nghim 1: t chy hon ton m (g) A thu c s mol CO2 v H2O bng nhau. Th nghim 2: Cho m (g) A phn ng vi dung dch AgNO3/ NH3 d thu c nAg = 2nA.Vy A l: A. Anehit no n chc (tr andehit fomic). B. Anehit no 2 chc. C. Anehit fomic. D. Cha xc nh c.
p n A 4. phn bit ancol CH2=CHCH2OH v anehit CH3CHO c th dng thuc th no sau y?

A. Dung dch brom. C. Dung dch AgNO3/NH3.

B. Dung dch thuc tm. D. C A, B, C

p n A

5. Hp cht hu c X khi un nh vi dung dch AgNO3/ NH3 (d) thu c sn phm Y. Cho Y tc dng vi dung dch HCl hoc dung dch NaOH u cho kh v c. X l:

A. HCHO. C. HCOONH4.

B. HCOOH. D. Tt c u ng.
p n D

6. Hp cht X c cng thc phn t l C3H6O tc dng c vi Na, H2 v tham gia phn ng trng hp.Vy X l:

A. Propanal. C. Ancol anlylic.

B. Axeton. D. Metyl vinyl ete.

p n C

7. Sn phm thu phn ca cht no di y c th tham gia phn ng trng gng?

A. CH2Cl CH2Cl. C. CH3 CCl3.

B. CH3 CHCl2. D. CH3COOCH(CH3)2.

p n B

304

8. Xc nh cng thc ca axit hu c A bit khi ho hi 3 (g) cht A thu c mt th tch hi A ng bng th tch hi ca 1,6 (g) oxi cng iu kin.

A. HCOOH. C. C2H5COOH.

B. CH3COOH. D. C2H3COOH
p n B

9. Thuc th no sau y dng phn bit hai cht lng l phenol v dung dch CH3COOH?

A. Kim loi Na. C. Dung dch NaHCO3.

B. Dung dch NaOH. D. Dung dch CH3ONa

p n C 10. Trong cc cht: HCCH; CH3OH ; HCOOH ; CH3COOH ; cht c tnh axit

mnh nht l: A. CH3OH. C. HCOOH.

B. CH3COOH. D. HCCH
p n C

11. Gi tn hp cht c CTCT nh sau theo danh php IUPAC.

CH2= CH CH2 CO CH CH3 CH3 A. isopropyl allylxeton. C. Allyliso-propylxeton. B. 2-metylhexen-5-on-3. D. 5-metylhexen-1-on-4.

p n B 12. Cho bit h s cn bng ca phn ng sau:

CH3CHO + KMnO4 + H2SO4 CH3COOH + MnSO4 + K2SO4 + H2O A. 5, 2, 4, 5, 2, 1, 4. C. 5, 2, 3, 5, 2, 1, 3. B. 5, 2, 2, 5, 2, 1, 2. D. C 3 u sai.

p n C 13. Ba cht hu c X, Y, Z mch khng nhnh c cng CTPT C2H4O2 v c tnh cht sau:

X tc dng c vi Na2CO3 gii phng CO2. Y tc dng c vi Na v c phn ng trng gng. Z tc dng c vi dung dch NaOH, khng tc dng c vi Na.
305

Xc nh X, Y, Z. A. X (HCOOCH3), Y (CH3COOH), Z (CH2(OH)CHO). B. X (CH3COOH), Y (CH2(OH)CHO), Z (HCOOCH3). C. X (CH2(OH)CHO), Y (CH3COOH), Z (HCOOCH3). D. X (CH3COOH), Y (CH2(OH)CHO), Z (HCOOCH3).
p n B 14. Cho bit sn phm chnh ca phn ng sau:

CH3 CH CH2 COOH CH3 A. CH3 CCl CH2COOH . CH3 B. CH2Cl CH(CH3) COOH.

as + Cl2 1:1

C. (CH3)2CH CHClCOOH. D. (CH3)2CH CH2 COCl.

p n C 15. C 5 bnh ng 5 cht lng sau: dung dch HCOOH, dung dch CH3COOH, ancol etylic, glixerol v dung dch anehit axetic. Dng nhng ha cht no sau y nhn bit c 5 cht lng trn. C. Nc brom, Cu(OH)2. A. AgNO3/NH3, qu tm. D. Cu(OH)2, Na2CO3. B. AgNO3/NH3, Cu(OH)2. p n C.

306

307

Mc lc
Chng VI. Hirocacbon khng no

Bi Bi Bi Bi Bi Bi Bi

39 40 41 42 43 44 45 -

Anken - Danh php, cu trc, ng phn........................................... 3 Anken - Tnh cht, iu ch v ng dng ........................................ 11 Ankaien ......................................................................................... 26 Khi nim v tecpen ........................................................................ 37 Ankin ............................................................................................. 45 Luyn tp: Hirocacbon khng no ................................................... 60 Thc hnh: Tnh cht ca hirocacbon khng no ............................ 71

Chng VII. Hirocacbon thm Ngun hirocacbon thin nhin Bi Bi Bi Bi Benzen v ankylbenzen .................................................................. 77 Stiren v naphtalen ......................................................................... 96 Ngun hirocacbon thin nhin ..................................................... 106 Luyn tp: So snh c im cu trc v tnh cht ca hirocacbon thm vi hirocacbon no v khng no ...................... 121 Bi 50 - Thc hnh: Tnh cht ca mt s hirocacbon thm ..................... 131 Chng VIII. Dn xut Halogen. Ancol - Phenol Bi 51 Bi 52 Bi 53 Bi 54 Bi 55 Bi 56 Bi 57 Dn xut halogen ca hirocacbon ............................................... 136 Luyn tp: Dn xut halogen ......................................................... 151 Ancol - Cu to, danh php, tnh cht vt l ................................... 159 Ancol - Tnh cht ho hc, iu ch v ng dng .......................... 170 Phenol .......................................................................................... 186 Luyn tp: Ancol, phenol ............................................................... 199 Thc hnh: Tnh cht ca mt vi dn xut halogen, ancol v phenol .......................................................................................... 206 46 47 48 49 -

308

Chng IX. Anehit - xeton - Axit cacboxylic Bi 58 - Anehit v xeton ........................................................................... 212 Bi 59 - Luyn tp: Anehit v xeton .......................................................... 229 Bi 60 - Axit cacboxylic: Cu trc, danh php v tnh cht vt l ................. 241 Bi 61 - Axit cacboxylic: Tnh cht ho hc, iu ch v ng dng ............ 249 Bi 62 - Luyn tp: Axit cacboxylic ............................................................. 264 Bi 63 - Bi thc hnh: Tnh cht ca anehit v axit cacboxylic ................ 276 n tp cui nm .......................................................................................... 281

309

Thit k bi ging Ho hc 11 Nng cao Tp Hai TS. Cao C gic (Ch bin)

Nh xut bn H Ni

Chu trch nhim xut bn: Nguyn Khc Onh Bin tp: Phm Quc Tun V ba: To Thanh Huyn Trnh by: Thu Hng Sa bn in: Phm Quc Tun

310

In 1000 cun, kh 17 x 24cm, ti X nghip in ACS Vit Nam Km 10 ng Phm Vn ng Kin Thu Hi Phng Giy php xut bn s: 208 2007/CXB/46p TK 47/HN In xong v np lu chiu qu I/2008
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