Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

HA HU C
CHNG I TIT 1: I CNG HA HC HU C HP CHT HU C V HA HC HU C

I. Khi nim. 1/ Hp cht hu c: L hp cht ca C tr(CO, CO2, cc mui cacbonat, xianua, cacbua ca kim loi v amoni). S lng hp cht hu c rt nhiu c gi l hp cht hu c v nhng cht c nghin cu ban u ch c trong c th ngi, ng thc vt. 2/ Ha hc hu c: L ngnh ha hc chuyn nghin cu cc hp cht hu c II. Phn loi hp cht hu c. 1/ Da vo thnh phn nguyn t Hidrocacbon: CTTQ CxHy hoc CnH2n+2-2a(a = + v) bt bo ha ca phn t(nu cch xc nh). - Hidrocacbon no - Hidrocacbon khng no - Hidrocacbon thm Dn xut ca hidrocacbon: cc loi dn xut v cch phn loi trong mi loi dn xut - Dn xut halogen - Dn xut oxi - Dn xut nit 2/ Da vo mch C Hp cht khng vng(mch h) Hp cht mch vng 3/ Mt s khi nim lin quan * Nhm chc: L nhm nguyn t gy nn nhng phn ng ha hc c trng cho hp cht hu c Cc loi nhm chc - Nhm chc gn vi mch: C=C; C C: VD - Nhm chc c oxi + -OH; -O-: VD + -CHO; -CO- : VD + -COOH; -COO- : VD - Nhm chc c nit: -NH2; -NH- chc amin. : VD * Hp cht n chc l hp cht hu c ch cha mt nhm chc VD: * Hp cht a chc l hp cht hu c cha 2 hay nhiu nhm chc cng loi (cn gi l thun chc) VD: * Hp cht tp chc l hp cht cha 2 hay nhiu loi nhm chc khc nhau VD: Cch hnh thnh cng thc tng qut * Bc cacbon - Bc 0: VD - Bc 1, 2, 3, 4.: VD III. c im chung ca cc hp cht hu c. 1/ Thnh phn cu to - Thnh phn nguyn t: Nht thit c C, thng c H hay gp O, N ri n cc nguyn t halogen - Thnh phn lin kt: Lin kt ha hc ch yu trong hp cht hu c l lin kt CHT(gii thch) 2/ Tnh cht

Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

- Tnh cht vt l: Phn ln cc hp cht hu c thng khng tan hoc rt t tan trong nc, nhng tan trong dung mi hu c(gii thch) - Tnh cht ha hc + Cc hp cht hu c tng i d bay hi, km bn i vi nhit v d chy(gii thch) + Cc phn ng ha hc ca cc hp cht hu c thng din ra chm v theo nhiu hng khc nhau to thnh hn hp sn phm.(do cn nh hng sn phm chnh bng nhit hay xc tc). (gii thch) IV. Danh php hp cht hu c. 1/ Phn loi v danh php 2/ Danh php IUPAC. - Danh php thay th - Danh php gc - chc TIT 2: PHNG PHP TINH CH, TCH HP CHT HU C

I. Cc phng php thng thng. 1/ Phng php chit. - Nguyn tc: Tch cc cht lng khng tan vo nhau - Cch tin hnh 2/ Phng php kt tinh - Nguyn tc: Da vo tan ca cht trong mt dung mi nhit xc nh - Cch tin hnh: Ha tan cht cn tinh ch hay tch vo dung mi un nng c dung dch bo ha. Sau lm lnh dung dch, cht c tan nh s kt tinh trc. 3/ Phng php chng ct - Chng ct thng + Nguyn tc: Tch cc cht c nhit si khc nhau nhiu ra khi hn hp. + Cch tin hnh: - Chng ct phn on + Nguyn tc: Tch cc cht c nhit si khc nhau khng nhiu lm ra khi hn hp. + Cch tin hnh: - Chng ct li cun hi nc + Nguyn tc: Tch cht c nhit si cao ra khi hn hp. + Cch tin hnh: Cho hi nc i qua hn hp cn tch, hi nc lm cht cn tch bay hi theo. II. Phng php sc k TIT 3: THNH PHN NGUYN T V CNG THC PHN T

I. Cc loi cng thc hp cht hu c. - CTTQ: Cho bit thnh phn nguyn t c trong hp cht + CTTQ ca hidrocacbon(iu kin ca x, y ) + CTTQ ca dn xut(iu kin ca x, y, z) - CTG, CTTG: Cho bit t l s nguyn t ca cc nguyn t c trong hp cht hu c VD: - CTTN: Tng t cng thc n gin VD: - CTPT: Cho bit s nguyn t ca cc nguyn t trong hp cht VD: - CTCT: Cho bit th t lin kt ca cc nguyn t c trong hp cht. II. Phn tch nguyn t. 1/ Phn tch nh tnh.

Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

* Mc ch: Xc nh thnh phn nguyn t to nn hp cht. * Nguyn tc: Chuyn hp cht cn xc nh thnh cc hp cht v c n gin, d nhn bit, sau nhn bit chng bng cc phn ng ha hc c trng. a/ Xc nh C, H - Cch tin hnh: un nng hchc vi CuO(khng t bng khng kh v c nhiu tp cht). Nhn bit hi nc bng CuSO4 khan, CO2 bng nc vi trong - Ch nhn bit chnh xc ta nhn bit hi nc trc, CO2 sau b/ Xc nh N. - t chy hp cht hu c c mi kht N - un hp cht hu c vi Na NaCN Fe2+ + 6CN- [Fe(CN)6]44Fe3+ + 3[Fe(CN)6]4- Fe4[Fe(CN)6]3 (mu xanh m) - un nng hp cht hu c vi H2SO4 c, chuyn N thnh (NH4)2SO4, cho kim d vo sn phm thu c thy c kh mi khai bay ra v lm xanh qu tm m c/ Xc nh halogen. t hp cht hu c bng ancol etylic thu c kh hidro halogenua, dn kh vo dung dch AgNO3 thy c kt ta, kt ta li b ha tan trong NH3 c halogen. d/ nh tnh oxi. - Phng php trc tip kh thc hin VD: Phn hy hp cht hu c cha oxi thnh CO, sau cho tc dng vi I2O5CO2 + I2 nhn bit s c mt ca iot bng h tinh bt - Phng php gin tip: t phn tch nh lng mO = mh/c - mC mH 2. Phn tch nh lng. * Mc ch: Xc nh hm lng % cc nguyn t c trong hp cht (xc nh CTG hay CTTN) * Nguyn tc: chuyn ha hon ton cc nguyn t trong hp cht hu c thnh cc hp cht v c n gin, sau nh lng cc hp cht v c thng qua th tch, khi lng, t tnh c phn trm ca cc nguyn t (theo nh lut bo ton nguyn t). 3. Phng php xc nh. * Nguyn tc: Da theo nh lut bo ton nguyn t: Lng mt nguyn t trong cc cht tham gia phn ng bng lng nguyn t trong cc cht sn phm a/ nh lng C, H t chy hon ton hp cht hu c bng CuO hay O2 nguyn cht nhit cao (khng dng khng kh) sn phm chy c CO2 v H2O. nh lng chng dng cc phng php sau: + nh lng ring: phi nh lng H2O trc, CO2 sau - nh lng nc bng cch cho sn phm i qua cc bnh ng cht ht m, hp th H2O (ch cc cht ny khng c tnh baz) nh P2O5, H2SO4, CaCl2, CuSO4. S tng v khi lng ca bnh ng chnh l khi lng H2O b hp th - nh lng CO2, kh i ra khi bnh hp th H2O cho i vo bnh ng cc cht c tnh baz nh CaO, dung dch kim. nh lng CO2 thng qua s tng khi lng bnh ng hay da vo lng kt ta. + nh lng c CO2 v H2O. V nhng cht hp th CO2 th cng c kh nng hp th H2O nn ta cho sn phm chy vo bnh ng cht hp th nh dung dch Ba(OH)2, Ca(OH)2 (nc vi trong) d, hoc dng lng hp th ht sn phm chy. - Nu dng d cc dung dch hp th th T m xc nh c CO2 Khi lng bnh ng tng m = mCO2 + mH 2 O Nu khi lng dung dch tng th: m = mCO2 + mH 2 O - m Nu khi lng dung dch gim th: m = m - ( mCO2 + mH 2 O ) - Khi dng a mol Ca(OH)2 hay Ba(OH)2 m thu c b mol kt ta (b < a) th ta phi xt 2 trng hp Ch c phn ng to kt ta (to mui trung ha)

Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

C c phn ng to mui trung ha v to mui axit b/ nh lng N - Cch 1: dng phng php Dumass Oxi ha hon ton hp cht hu c bng CuO, O2 thu c CO2, H2O, N2 Cho ton b sn phm chy i qua bnh ng dung dch kim c (Hnh v) N2, hi nc h A B PA = PB Pkq = Pnit + Phi nc bo ha + Pct nc Pkq = Pnit + Phi nc bo ha + h/13,6 Cch 2: Phng php Kiecdan. Chuyn ha N trong hp cht hu c thnh NH3, ri nh lng NH3 bng axit c. nh lng halogen Chuyn ha hp cht hu c cha halogen thnh cc axit halogen hidric tng tng, cho sn phm tc dng vi dung dch AgNO3, ri nh lng kt ta. d. nh lng oxi. - Phng php trc tip - Phng php gin tip V d 1: t chy 11,6 gam cht A thu c 5,3 gam Na2CO3; 4,5 gam H2O v 24,2 gam CO2. Hm lng C trong A l V d 2: t chy hon ton 7,4 gam cht hu c A bng mt lng oxi va . Sn phm chy cho hp th hon ton vo bnh ng dung dch Ca(OH)2 d(khng c kh thot ra), thu c 40 gam kt ta, lc b kt ta thu dung dch thy khi lng dung dch gim 13,4 gam so vi dung dch ban u. Hm lng O trong A l V d 3: t chy hon ton 0,282 gam hp cht hu c B ri cho sn phm chy ln lt qua bnh 1 ng CaCl2 khan v bnh 2 ng KOH rn. Sau th nghim, khi lng bnh 1 tng 0,194 gam v bnh 2 tng 0,80 gam. Mt khc, khi t chy hon ton 0,186 gam B thu c 22,4 ml kh N 2 (ktc). Phn t B ch cha 1 nguyn t nit. Xc nh CTPT ca B. V d 4: t chy hon ton mt lng hp cht hu c A (thnh phn cha C, H, Cl) thu c 0,44gam CO2 v 0,18 gam H2O. Khi xc nh lng Clo trong cng mt lng cht A bng dung dch AgNO3 d th thu c 2,87 gam AgCl. Phn trm khi lng ca Cl trong A l III. Xc nh phn t khi 1. Da vo khi lng v s mol - Khi lng cht thng c u bi cho - Xc nh s mol ca cht da vo th tch thng qua phng trnh trng thi. Hoc xc nh s mol da vo s mol ca cht cho cng th tch cng iu kin v nhit , p sut 2. Da vo t khi. M dA / B = A MA = MB . dA/B MB - i vi khng kh chn M = 29 - Trong trng hp hn hp kh ta phi tnh phn t khi trung bnh VD cho hn hp kh A, B vi s mol tng ng nA, nB, thit lp cng thc tnh phn t khi trung bnh ca hn hp kh m m + mB M = hh = A nhh nA + nB 3. Da vo nh lut Raun

Trng THPT Chuyn Bc Ninh Vn Bnh

ts = Ks . Cm (Cm l s mol cht tan c trong 1000 gam dung mi) t = K . Cm Gi thit trong a gam cht tan c m gam dung mi ta c cng thc t = K . 100 m M ct.a

Th/s Ng

4. Phng php o ph khi lng y l phng php hin i tin hnh nhanh, lng mu nh v chnh xc IV. Thit lp cng thc phn t hp cht hu c. 1. Thit lp cng thc n gin-cng thc thc nghim. Gi thit hp cht hu c c cng thc tng qut l CxHyOzNt tm t l s nguyn t ca cc nguyn t ta s mt trong 3 cch sau: x : y : z : t = nC : nH : nO : nN mC mH mO mN : : : 12 1 16 14 %C %H %O %N = : : : 12 1 16 14 Nguyn ha cc s liu bng cch chia cc s cn li cho s nh nht. Nu vn cha c th c th nhn thm vi 2;5... V d 1: Trong mt hp cht hu c c hm lng cc nguyn t ln lt l 51,3%C ; 9,4%H ; 12,0%N ; 27,3%O. Cng thc n gin nht ca hp cht hu c? Hng dn Gi cng thc tng qut hp cht hu c l C xH yOz N t C =

x : y: z : t =

%C %H %O %N : : : 12 1 16 14 51,3 9,4 27,3 12 = : : : 12 1 16 14 = 4,275 : 9,400 :1,706 : 0,857 = 5 :11 : 2 :1

Vy cng thc n gin ca hp cht hu c l C5H11O2N V d 2: Khi phn tch mt hp cht hu c thy: c 2,1 phn khi lng C th c 2,8 phn khi lng oxi v 0,35 phn khi lng hiro. Cng thc n gin ca hp cht hu c l Hng dn Gi cng thc tng qut ca hp cht hu c l C xH yOz m m m x : y: z = C : H : O 12 1 16 = 0,175 : 0,35 : 0,175

= 1 : 2 :1 Vy cng thc n gin l CH2O p n B. V d 3: t chy hon ton 5,2 gam hp cht hu c A ri cho sn phm chy ln lt qua bnh 1 ng H2SO4 c v bnh 2 ng dung dch nc vi trong d. Sau th nghim thy khi lng bnh 1 tng 1,8 gam v bnh 2 c 15 gam kt ta. Cng thc n gin ca A l Hng dn Theo u bi c mH 2 O = 1,8g nH 2 O = 0,1mol nH = 0,2mol mH = 0,2g
mO = mA mC mH = 3,2g nO = 0,2mol Gi cng thc tng qut ca hp cht hu c l CxH yOz
mCaCO3 = 15g nCaCO3 = 0,15mol nCO2 = 0,15mol nC = 0,15mol

Trng THPT Chuyn Bc Ninh Vn Bnh

x : y : z : t = nC : nH : nO : nN

Th/s Ng

= 0,15 : 0,2 : 0,2 = 3:4 :4 Vy cng thc n gin ca A l C3H4O4 p n D. 2. Xc nh cng thc phn t t hm lng cc nguyn t. Vi hp cht hu c A c cng thc tng qut C xH yOz N t . - Nu bit hm lng cc nguyn t ta c th xc nh cng thc phn t bng mt trong cc cch sau

12.x y 16.z 14.t 12.x + y + 16.z + 14.t M A = = = = = mC mH mO mN mA mA

(IV.1)

12.x y 16.z 14.t 12.x + y + 16.z + 14.t M A = = = = = (IV.2) %C %H %O %N 100 100 - Nu bit cng thc n gin C xH yOz N t th cng thc phn t s c dng (C xH yOz N t )n . Khi bit khi lng phn t M ta s xc nh c h s n. M = (12.x + y + 16.z + 14.t).n (IV.3) V d 1: Cho bit trong mt hp cht hu c X hm lng cc nguyn t ln lt l 54,5%C ; 9,1%H v 36,4%O. Bit 1,76 gam hi cht hu c chim th tch 448 ml (ktc). Cng thc phn t ca hp cht hu c X l Hng dn Gi cng thc ca X l C xH yOz 1,76 MX = = 88(vC ) 0,448 C 22,4 M .%C = 4 ; tng t c y = 8; z = 2. T cng thc IV.2 x = X 12.100 Vy cng thc phn t ca X l C4H8O2 V d 2: Khi phn tch mt hp cht hu c Y thy: c 2,10 phn khi lng C th c 2,80 phn khi lng oxi v 0,35 phn khi lng hiro. ktc, 1 g cht Y chim th tch 373,3 cm 3. Cng thc phn t ca Y l Hng dn Gi cng thc ca X l C xH yOz Gi thit c mC = 2,1 gam; mH = 0,35 gam; mO = 2,8 gam. mY = mC + mH + mO = 5,25 gam.
1 = 60(vC ) 0,3733 Theo u bi c 22,4 p dng cng thc IV.1 ta s thu c x = 2; y = 4; z = 2. Vy cng thc phn t ca Y l C2H4O2 p n D. 3. Xc nh cng thc phn t t cng thc n gin. lm c theo phng php ny ta cn xc nh c CTG v bit c phn t khi, gii hn phn t khi, iu kin v s nguyn t ca mt nguyn t no trong phn t. V d 1: Khi phn tch mt hp cht hu c A thy: c 2,1 phn khi lng C th c 2,8 phn khi lng oxi v 0,35 phn khi lng hiro. Xc nh cng thc phn t ca hp cht hu c trong cc trng hp sau. a/ T khi hi ca A so vi heli bng 45. b/ T khi hi ca A so vi hidro nh hn 30. c/ A l mt axit hu c n chc. MY =

Hoc

Trng THPT Chuyn Bc Ninh Vn Bnh

Hng dn Gi cng thc tng qut ca hp cht hu c l C xH yOz m m m x : y: z = C : H : O 12 1 16 = 0,175 : 0,35 : 0,175

Th/s Ng

= 1 : 2 :1 Vy cng thc n gin l CH2O cng thc nghim ca A l (CH2O)n v MA = 30.n a/ T t khi MA = 180 30.n = 180 n = 6 CTPT ca A l C6H12O6. b/ T t khi MA < 60 30.n < 60 n < 2 n= 1 CTPT ca A l CH2O. c/ A l mt axit hu c n chc nn c cha mt nhm COOH, vy trong A c cha 2 nguyn t oxi, do n =2 CTPT l C2H4O2. 4. Dng xc nh cng thc phn t hp cht hu c theo phng trnh phn ng chy. Gi thit hp cht hu c A c cng thc tng qut l C xH yOz N t Phng trnh phn ng chy y z y t C xH yOz N t + (x + )O2 xCO2 + H 2 O + N 2 4 2 2 2 Theo phng trnh phn ng ta c t l h s gia cc cht bng t l v s mol ca chng, cng iu kin v nhit v p sut t l cng bng t l v th tch ca cc hp cht nCO2 VCO2 x nCO2 VCO2 = = x= = 1 nA VA nA VA nH O VH O y nH 2 O VH 2 O = = y = 2. 2 = 2. 2 2 nA VA nA VA
nN VN t nN 2 VN 2 = = t = 2. 2 = 2. 2 2 nA VA nA VA

(x +

nCO2 nH 2 O nO y z nO2 VO2 )= = z = 2. + 2. 2 4 2 nA VA nA nA nA = 2. VCO2 VA + VH 2 O VA 2. VO2 VA

Ta cng c th xc nh z khi bit MA. MA = 12.x + y + 16.z + 14.t V d 1: t chy hon ton 1 lt kh A cn 5 lt O2, thu c 3 lt CO2 v 4 lt H2O. Cc th tch o cng iu kin nhit v p sut. Cng thc phn t ca A l Hng dn Gi cng thc hp cht hu c A l C xH yOz Phng trnh phn ng chy y z y CxH yOz + (x + )O2 xCO2 + H 2 O 4 2 2 p dng cc cng thc trn ta c x = 3; y = 8; z = 0. Vy cng thc phn t ca A l C3H8. V d 2: Trn 400 ml hn hp kh (gm N2 v mt hirocacbon) vi 900 ml O2(d) ri t. Th tch ca hn hp kh v hi sau khi t l 1400 ml. Sau khi ngng t hi nc, th tch hn hp cn 800 ml, cho hn hp qua dung dch KOH, th tch cn li l 400 ml. Cc th tch kh v hi c o cng iu kin. Xc nh CTPT ca hirocacbon. Hng dn Gi cng thc hirocacbon l C xH y . t th tch ca Hirocacbon l a, th tch ca N2 l b. C a + b = 400.

Trng THPT Chuyn Bc Ninh Vn Bnh

Phng trnh phn ng chy

Th/s Ng

y y CxH yOz + (x + )O2 xCO2 + H 2 O 4 2 a (x + y/4).a a.x a.y/2 Th tch hn hp gim i khi ngng t hi nc l th tch ca hi nc(600ml). Tip tc cho hn hp i qua dung dch KOH th tch gim i l th tch ca CO 2 b hp th(400ml). Hn hp cn li l ca N2 v O2 d. Nn ta c h a + b = 400 a.x = 400 a.y / 2 = 600 b + 900 a.(x + y / 4) = 400 Gii h ta c a = b = 200; x = 2; y = 6. Vy cng thc phn t ca hirocacbon l C2H6 V d 4: t chy ht hirocacbon B bng mt lng O2 va th th tch kh CO2 thu c bng mt na tng th tch ca B v O2. S cng thc phn t ca B tho mn iu kin l Hng dn Gi cng thc ca B l C xH y (y 2 x + 2)
Ptp: C xH y + (x + y / 4)O2 xCO2 + y / 2H 2 O 1 (x + y/4) x Theo u bi 2.x = 1 + x + y/4 4x = y + 4. tho mn iu kin ca y ch c 2 cp nghim x = 2; y = 4 v x = 3; y =8. 5. Xc nh cng thc phn t hp cht hu c khi bit khi lng phn t. Gi thit hp cht hu c A c cng thc tng qut l C xH yOz N t Trong x, y, z, t l cc s nguyn dng v y 2.x + t + 2 M = 12.x + y + 16.z + 14.t Ta lp bng bin lun bt u t bin no c h s ln nht. Trong v v trn ta bt u bin lun theo bin z. V d 1: Mt hirocacbon c t khi so vi hiro bng 28. Cng thc phn t ca hirocacbon l Hng dn Gi cng thc ca hirocacbon l CxHy (y 2.x + 2) d = 28 M = 28.2 = 56 12.x + y = 56 x 1 2 3 4 5 y 44 32 20 8 -4 Vy cng thc phn t ca hirocacbon l C4H8 V d 2: S cng thc phn t hp cht hu c (c thnh phn nguyn t gm C, H v O) c cng khi lng phn t 60 l Hng dn Gi thit hp cht hu c c cng thc tng qut l C xH yOz Trong x, y, z l cc s nguyn dng v y 2.x + 2 M = 12.x + y + 16.z = 60 z 1 2 3 x 1 2 3 4 1 2 3 1 y 32 20 8 -4 16 4 -8 0 Vy c 2 cng thc phn t tho mn l C3H8O v C2H4O2 V d 3: Mt hidrocacbon A khi cho tc dng vi Brom thu c sn phm B, t khi hi ca B so vi khng kh bng 5,207. Cng thc phn t ca B l Hng dn Gi thit hp cht hu c c cng thc tng qut l CxH yBrz

Theo u bi B c M = 151 < 2*80 trong B ch c 1 Br, nn cng thc ca B ch c th l C5H11Br.

Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

TIT 4

CU TO HA HC-CU TRC KHNG GIAN

I. Thuyt cu to ha hc. Ni dung thuyt cu to ha hc ca Butlerop * Trong phn t hp cht hu c, cc nguyn t kt hp vi nhau theo mt th t nht nh v theo ng ha tr ca chng. Th t gi l cu to ha hc. S thay i th t kt hp s to ra cht mi. * Trong phn t hp cht hu c, C c ha tr 4. Cc nguyn t cacbon c th kt hp khng nhng vi nguyn t ca cc nguyn t khc m cn kt hp trc tip vi nhau thnh nhng mch cacbon khc nhau. * Tnh cht cc hp cht hu c ph thuc vo thnh phn phn t(bn cht v s lng cc nguyn t) v cu to ha hc(th t kt hp cc nguyn t). II. Cng thc cu to. 1/ Khi nim: L cng thc biu din th t lin kt ca cc nguyn t trong phn t. CTCT cho bit loi lin kt, th t lin kt, cc thc lin kt ca cc nguyn t trong phn t. 2/ Cch thc biu din CTCT. - CTCT khai trin(chi tit): biu din tt c cc lin kt trong phn t - CTCT thu gn: vit gp cc nguyn t H vi cc nguyn t m chng lin kt thnh cc nhm - CTCT thu gn nht: ch dng on thng biu din lin kt gia cc nguyn t C. u mt cc on thng l cc nhm CHx sao cho C c ha tr 4. Cc nguyn t khc v cc nhm chc gi nguyn. VD 1: vit cc cng thc cu to c th c ng vi cng thc phn t C 4H8 theo c 3 cch biu din CTCT. VD 1: vit cc cng thc cu to c th c ng vi cng thc phn t C4H8O theo c 3 cch biu din CTCT. 3. Cch xc nh CTCT. xc nh CTCT ngi ta p dng cc phng php thc nghim xc nh cu to bao gm: phng php ha hc (da vo tnh cht) v phng php vt l (da vo nhit nng chy, nhit si..) 4. ngha. - Thuyt cu to ha hc cho bit mi lin h gia cu to ha hc v tnh cht ca hp cht hu c. Khi bit cu to ha hc c th d on c tnh cht v ngc li. - L c s khoa hc cho cc nghin cu phn tch l thuyt v ha hc hu c v ng dng ca hp cht hu c trong i sng. III. ng ng, ng phn. A. ng ng. 1. Khi nim: L hin tng cc cht c cu to v tnh cht tng t nhau, nhng thnh phn phn t khc nhau mt hay nhiu nhm cu trc nht nh, thng l nhm metylen -CH2, c th l CH(OH)... Nhng cht gi l ng ng vi nhau v chng hp thnh dy ng ng. VD: - Dy ng ng ca metan - Dy ng ng ca etilen - Dy ng ng ca ancol - Dy ng ng ca ancol no a chc, tp chc (cacbohidrat) 2. Nhn xt. (trong chng trnh ph thng ch xt cc ng ng hn km nhau nhm CH2) * Cc cht cng dy ng ng c - Cng cng thc chung (CTTQ) - Cu to v tnh cht tng t nhau

Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

- Khi lng phn t hn km nhau bi s ca 14 * Cc cht ng ng lin tip l cc cht hn km nhau mt nguyn t C, phn t khi hn km nhau 14u. * Ch : Cc cht c cng cng thc tng qut cha chc l ng ng ca nhau. xc nh ng ng chng ta phi da vo cng thc cu to. * Trong bi tp cho cc cht cng dy ng ng ta s dng cng thc trung bnh (cng thc tng ng) VD 1: Cho hn hp 2 cht C2H6(0,2 mol) v C3H8(0,3 mol). T cng thc ca 2 cht cng thc tng qut cng thc trung bnh c dng - Cch tnh phn t khi trung bnh - Cch tnh s nguyn t cacbon trung bnh - Cch tnh s nguyn t hidro trung bnh Cng thc ng cho xc nh t l mol VD 2: t chy hon ton 2 ankan l ng ng lin tip thu c CO2 v H2O theo t l th tch l 16:21. Xc nh cng thc 2 ankan v tnh phn trm khi lng, s mol, th tch ca mi cht c trong hn hp. B. ng phn. 1. Khi nim. K/n: L nhng cht khc nhau c cng cng thc phn t. L nhng cht c cng CTPT nhng c cu trc ha hc(CTCT, cu trc khng gian) khc nhau nn c tnh cht khc nhau (cu trc khng gian l s phn b trong khng gian ca cc nguyn t trong phn t). Do vy vi cng mt CTPT, th t lin kt cha chc phi cng mt cht. VD: mt trng hp ng phn hnh hc. 2. Nhn xt. - Cc cht c cng khi lng phn t, cng thnh phn nguyn t cha chc l ng phn ca nhau. VD: Cc cht c cng khi lng phn t 44 gm CTPT gm C3H8 hoc C2H4O. CH2-CH2 O Vi C2H4O c th c cc ng phn CH3-CH=O hoc CH2=CH-OH hoc 3. Phn loi. * ng phn cu to: C th t lin kt khc nhau. Gm + ng phn nhm chc. + ng phn mch C. + ng phn v tr nhm chc. * ng phn lp th: C th t lin kt ging nhau, nhng khc nhau v s phn b ca cc nguyn t hay nhm nguyn t trong khng gian. Gm 2 loi + ng phn hnh hc. + ng phn quang hc. a. ng phn cu to. * ng phn mch C - ng phn mch khng nhnh (mch thng) - ng phn mch c nhnh VD: * ng phn nhm chc, loi lin kt - ng phn loi lin kt nh: anken=xicloankan, ankin=ankadien VD: - ng phn loi nhm chc: ancol-ete; andehit-xeton... VD: * ng phn v tr nhm chc, v tr lin kt bi. VD: * ng phn h bin (ng phn tautome): y l loi ng phn c bit, 2 ng phn tn ti trong cng mt cn bng, ng phn ny chuyn ha thnh ng phn kia qua s thay i v tr ca 1 nguyn

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Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

t H dn n s thay i ca 1 lin kt i. Cn bng gia 2 ng phn ny gi l cn bng h bin hay s h bin. VD: CH3-CH=O (100% dng xeto) CH2=CH-OH (dng enol) CH3-C-CH2-COOC2H5 CH3-C=-CH-COOC2H5 OH O Xeto - Chuyn ha nitro axi O CH3-CH2-N Enol OH CH3-CH=N

O O Ch : Trong cc ng phn h bin, ty theo bn ca cc ng phn m trong cn bng dng ng phn no s chim ch yu. VD O O Dng enol bn hn do to c lin kt H (vng 5 cnh) chim 100% * Cc bc vit ng phn cu to. + Bc 1: xc nh bt bo ha( khng no a = lin kt + vng) 2x + 2 y (a 0) - Vi hp cht CxHyOz(St) a = 2 O, S khng nh hng n bt bo ha ca phn t. 2x + 2 y z (a 0) X l cc halogen - Vi hp cht CxHyXz a = 2 2x + 2 y + z (a 0) trong x, y cng l hoc cng chn. - Vi hp cht CxHyNz a = 2 VD: Xc nh bt bo ha ca cc cht sau C6H12O6, C6H7N, C5H6Cl2 + Bc 2: Xc nh loi nhm chc, loi lin kt. VD: Xc nh loi hp cht ng vi CTPT C5H10O ancol-ete(mch h, mch vng), andehit-xeton + Bc 3: Vit cc kiu mch C. - ng phn mch h khng nhnh, ng phn mch h c nhnh(1 nhnh, 2 nhnh, 3 nhnh...) - ng phn mch vng khng nhnh, mch vng c nhnh + Bc 4: Vit cc ng phn v tr theo tng kiu mch C - ng phn v tr lin kt bi, v tr nhm chc (ch ti tnh i xng ca mch) VD: Vit cc ng phn ng vi CTPT C6H14; C4H8O; C3H9N; C5H10; C4H7Cl; C4H8Cl2, C4H8BrCl. b. ng phn lp th. * Cc cch biu din cu trc phn t trong khng gian. + Cng thc phi cnh: - Lin kt nm trn mt phng giy: 1 nt gch bnh thng - Lin kt nm sau mt phng giy: nt t --- hay - Lin kt nm trc mt phng giy: nt lin m hay (gn ngi quan st u lin kt s to hn) VD O

...H O

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Trng THPT Chuyn Bc Ninh Vn Bnh

H H H C H

Th/s Ng
H

C H H

H H H Vi phn t ln, lin kt to mch c xt nm trn mt phng giy + Cng thc Niumen: Nhn phn t dc theo mt lin kt no , thng l lin kt C-C, cc nguyn t cacbon l cc hnh trn ng tm, nguyn t ng trc l 1 du chm-cc lin kt c biu din t tm, nguyn t ng sau l mt hnh trn-cc lin kt c biu din t gii hn ca ng trn. VD: H HH H H H H H H

+ Cng thc chiu Fis: - Chn mt phng giy i qua nguyn t C - Lin kt nm ngang l lin kt nm trc mt phng giy. - Lin kt nm dc l lin kt nm sau mt phng giy. VD
F H C Cl F Cl OH H C OH H Cl F OH

Quy i ngc li CHO H CH2OH OH H CHO H OH OHC CH2OH C OH CH2OH

Ch : Cng thc phi cnh v cng thc Niumen biu din phn t theo c 3 chiu trong khng gian (tri-phi, trn-di, trc-sau) do khi quay phn t mt gc bt k khng lm thay i cht (khng to ra ng phn) Cng thc Fis ch biu din theo 2 chiu (tri-phi, trn di) khng biu din mi lin h trc sau. Do khng ty tin xoay phn t mt gc no , khi xoay 90 0 hay 2700 thu c ng phn i quang (c C*) * ng phn hnh hc: L nhng ng phn c cng cng thc cu to nhng c dng hnh hc khc nhau hoc l nhng ng phn c cng CTCT nhng v tr khng gian ca cc nhm nguyn t trong phn t xung quanh b phn cng nhc khc nhau (lin kt i hoc vng) VD: But-2-en

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Th/s Ng

+ Nguyn nhn gy ra ng phn hnh hc: mt phng lin kt i hay vng no khng th t do quay xung quanh trc lin kt. cc nguyn t, nhm nguyn t lin kt vi cc b phn ny c nhiu cch sp xp trong khng gian khc nhau to thnh ng phn hnh hc. + iu kin c ng phn hnh hc - iu kin cn: trong phn t phi c b phn cng nhc, c mt phng lin kt i, mt phng vng no. - iu kin : mi nguyn t C b phn cng nhc c so snh phi lin kt vi 2 nguyn t hay nhm nguyn t khc nhau VD d c d b c a b C=C d c a a b Vi a b; c d + Vi hp cht c nhiu lin kt i lin nhau, s lin kt i chn khng c ng phn hnh hc, s lin kt i l c ng phn hnh hc. VD: + Vi hp cht c cc lin kt i cch nhau mt lin kt n C-C h lin hp, c ng phn hnh hc VD: vi phn t CH3CH=CH-CH=CH-CH3 c bao nhiu kiu ng phn hnh hc? + Tn gi ng phn hnh hc: - ng phn cis-trans: hp cht c lin kt i, vng no Mch chnh C cng pha vi nhau: ng phn cis Mch chnh C khc pha vi nhau: ng phn trans VD: CH3CH=C(CH3)-CH2CH3. - ng phn syn-anti, p dng cho hp cht c lin kt i CH=N v N=N Vi CH=N-: H v cp e ca N khc pha l ng phn syn, cng pha l anti Vi N=N 2 cp e cng pha l syn, khc pha l anti VD: C6H5-N=N-C6H5 v CH3CH=NH; CH3CH=NCH3 + Danh php E-Z - hn cp ca cc nhm th - Nguyn t c s th t ln hn nhm th c hn cp cao hn -Br > Cl > F > OH > NH2 > CH3 - Vi cng mt nguyn t - ng v no c s khi ln hn s c tnh hn cp cao hn. -C(CH3)3 < -C(CH3)=CH2 < -C CH -CH(OH)2 < -CH=O - cp electron t do c cho c tnh hn cp bng 0 - Nu cc nguyn t u cng cp th xt cc nguyn t tip theo - ng phn E-Z - Cc nhm th cao cp hn cng pha: ng phn Z - Cc nhm th cao cp hn khc pha: ng phn E. VD: CHCl=CCl-CH3 + Tnh cht ca cc ng phn hnh hc: Cc ng phn hnh hc c tnh cht ha hc tng t nhau nhng khc nhau v bn (G), nhit nng chy, nhit si, moomen lng cc, tan VD: cis-but-2-en c nhit nng chy thp hn trans-but-2-en do phn t c kh nng sp xp c kht hn, nhng ngc li c mmen lng cc, nhit si cao hn do cc nhm th i xng nhng khng ngc chiu. * ng phn quang hc

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Th/s Ng

+ Tnh cht quang hot l tnh cht khng trng nh-vt + Tnh quang hot l tnh cht lm quay mt phng nh sng phn cc 1 gc no Cht c tnh quang hot gi l cht quang hot o mnh yu s dng quay cc ring: : gc quay mt phng nh sng phn cc .V V: th tch cha cht quang hot t0 [] = l.d L: dy lp cht nh sng i qua D: khi lng ring ca cht quang hot + Tnh khng trng vt-nh: phn t c tnh khng trng vt-nh s c tnh quang hot + iu kin phn t c tnh khng trng vt nh: phn t phi khng c tm i xng, khng c trc i xng. - Nguyn t C bt i C*: 4 nhm th lin kt vi nguyn t C l khc nhau C*abcd (a b c d) - Phn t c 1C*: c tnh khng trng nh vt c tnh quang hot - Phn t c nhiu C*: Nu c tm i xng hoc mt phng i xng th khng c tnh quang hot, nu khng c tm i xng v mt phng i xng th c tnh quang hot + ng phn quang hc l nhng ng phn c cu to ha hc nh nhau, dng hnh hc ca phn t nh nhau v vy c tnh cht vt l v ha hc nh nhau, ch khc nhau v kh nng lm quay mt phng nh sng phn cc. - Nu phn t c tc dng lm quay mt phng nh sng phn cc sang phi mt gc th k hiu [+ ] cht quay phi - Nu phn t c tc dng lm quay mt phng nh sng phn cc sang tri mt gc th k hiu [- ] cht quay tri VD: axit lactic CH3-CH(OH)-COOH

COOH C CH3 H OH H

COOH C CH3

OH

Ax (+) lactic Ax (-) lactic Ax L(+ 3,8)-lactic Ax D(- 3,8)-lactic + Cc loi ng phn quang hc: - ng phn i quang: nh v vt qua gng VD: Ax L(+ 3,8)-lactic v Ax D(- 3,8)-lactic l cp i quang - ng phn meso: VD 1: COOH COOH H H OH OH COOH HO HO H H COOH

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Th/s Ng

Hai cng thc l 1, chng u c mt phng i xng nn khng c tnh quang hot v l ng phn meso hay l ng phn ia ca cp i quang (2 ng phn sau) COOH HO H H OH COOH H HO COOH OH H COOH

Hai ng phn ny l cp i quang ca nhau Nh vy axit tactric ch c 3 ng phn - S ng phn quang hc: Nu phn t c nC*, khng c tm i xng, mt phng i xng, trc i th c 2n ng phn quang hc. Nu phn t c mt trong cc yu t i xng th s ng phn quang hc < 2n. VD: OHC-CH(OH)-CH(OH)-COOH c 4 ng phn HOOC-CH(OH)-CH(OH)-COOH c 3 ng phn(mt ng phn meso) + Hn hp raxemic - L tp hp ng phn t (c s mol bng nhau) ca 2 ng phn i quang VD: bin th raxemic ax ( ) tactric gm ax (+) tactric v ax (-) tactric - Mt phng phn cc khng b quay do 2 ng phn i quang c chiu quay ngc nhau lm trit tiu s quay mt phng phn cc. * Cu hnh ca cc nguyn t C* + Cu hnh tng i (L, D) - Ly glixerandehit lm chun: CH2(OH)-CH(OH)-CHO
CHO OH HO CHO H CH2OH

CH2OH

D-glixeradehit L-glixerandehit Nhng cht c cu hnh ging L-glixerandehit L Nhng cht c cu hnh ging D-glixerandehit D VD: CH2OH-CHCl-CHO + Cu hnh tuyt i: Phn cp cc nhm th ca C*: C*abcd gi thit a > b > c > d Nhn lin kt C*-d t C* n d (C* gn ngi quan st, d xa ngi quan st) - Nu hn cp cc nhm th gim dn theo chiu ngc chiu kim ng h cu hnh S - Nu hn cp cc nhm th gim dn theo chiu cng chiu kim ng h cu hnh R OH OH C H CH3 S- Xc nh cu hnh tuyt i t cu hnh tng i Fis RCl H Cl

C CH3

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Th/s Ng

Nu nhm th thp cp nht nm trn lin kt ngang. Khi hn cp ca cc nhm th cn li gim dn theo chiu kim ng h l cu hnh S, ngc li l cu hnh R Nu nhm th thp cp nht nm trn c thng ng th ngc li, theo chiu kim ng h l cu hnh R, ngc chiu kim ng h l cu hnh S. VD: Xc nh cu hnh tuyt i ca ng phn sau CHO H HO CH3 OH F

(2R, 3S)

IV. Cu dng. * K/n: Nhng cu dng l nhng cu trc khng gian khc nhau ca cng mt cht c to nn do s quay quanh trc lin kt n ca cc nhm th. VD: cc cu dng ca etan. Cu dng bn nht l dng xen k (cc cht khc c xen k k v xen k i). Cu dng km bn nht l cu dng che khut (do cc nhm th cng gn nhay th tng tc y cng mnh km bn)

TIT 5

DANH PHP HP CHT HU C

I. Tn thng thng. - L tn xut pht t ngun gc tm ra cht, i khi c thm ui ch loi hp cht VD: HCOOH (fomica) ax fomic CH3COOH (axtus) ax axetic II. Tn quc t-IUPAC. International Union Pure and Applied of Chemistry 1. Tn gc chc. a. Gc(nhm) hidrocacbon - L phn cn li ca hidrocacbon khi mt i mt hay nhiu nguyn t H - Mt i mt nguyn t H gc ha tr 1 Hidrocacbon Tn hidrocacbon Gc Tn gc CH4 Metan CH3Metyl -CH2Metylen C2H6 Etan C2H5Etyl CH3CH2CH3 Propan CH3CH2CH2Propyl CH3-CH(CH3)isopropyl (sec-propyl) gc bc 2 CH3CH2CH2CH3 Butan CH3CH2CH2CH2Butyl CH3CH2CH(CH3)Sec-butyl CH3-CH(CH3)2 Isobutan CH3-CH(CH3)-CH2Isobutyl (CH3)3CNeobutyl (Tert-butyl) gc bc 3 CnH2n+2 Ankan CnH2n+1Ankyl Ngoi ra cn mt s gc (nhm) thng dng : CH2=CH: Vinyl CH2=CH-CH2 : Anlyl C6H5: phenyl C6H5-CH2: benzyl

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Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

b. Tn nhm chc - Halogen : halogenua - ancol (OH) : ic - ete (-O-) : ete - xeton (-CO-) : xeton c. Danh php gc chc Tn phn gc (thng l gc hidrocacbon) + tn phn chc VD: CH3CH2OH ancol etylic CH3OCH2CH3 etyl metyl ete CH3Cl metyl clorua CH2=CH-C CH vinyl axetilen CH3COCH3 imetyl xeton 2. Tn thay th. * Tn mch C: C1C10 C11: undeca C12: dodeca C13 : trideca C14: tetradeca ........ C19: nonadeca C20: icosa * Tn nhm chc - No: ui an - Khng no: C=C: en 2(C=C): ien 3(C=C) : trien.. C C : in - OH ancol ui : ol (nu ng trc gi l hidroxyl) - CHO : al - CO- : on - COOH : ic - NH2, -NH-, N: amin (nu ng trc NH2 gi l amino) * Tn thay th: Tn phn th-mch nhnh (c th c hoc khng) + tn mch chnh + tn phn chc Ch : trc tn phn th v tn phn chc bao gi cng c s ch v tr C m chng lin kt, gia s v ch bao gi cng cch nhau mt gch ngang (-). VD: CH2=CH-CH3 CH3CH(OH)CH3 . * Quy tc chn mch chnh v nh s th t - Chn mch di nht c cha nhm chc, cha lin kt bi, cha nhiu nhnh - nh s th t C trn mch chnh theo chiu t u mch no sao cho tng s ch v tr nhm chc, lin kt bi, mch nhnh l nh nht. VD: CH3-CH=C(Cl)-CH3 CH3-C(CH3)2-CH(OH)-CH2-CH3

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TIT 6 HIU NG CU TRC

Th/s Ng

A. LIN KT CNG HA TR. I. Cc cch biu din CTCT ca cht 1. Cng thc Lewis: biu din cc cp electron bng du chm v lin kt bng nhng nt gch. VD: CH3-NO2 C6H6

.O.. .. CH -N ..O..
3

Mt cht c th biu din bng nhiu CTCT, gia cc cng thc cu to c th chuyn ha ln nhau 2. Cng thc cng hng. - Theo thuyt cng hng mi cht c nhiu cng thc nhng khng cng thc no ng, ph hp hon ton vi tnh cht vt l, ha hc ca cht. Cht s c biu din tt hn bng cng thc lai ha gia cc cng thc O ... .. CH -N . .O
3

II. Lin kt cng ha tr. 1. S xen ph gia cc AO, lin kt , lin kt . Lin kt n, lin kt bi. * Phn loi lin kt CHT - Theo hnh thc gp electron: CHT thng thng, CHT cho-nhn - Theo s phn cc lin kt: CHT khng cc, CHT c cc - Theo s lng cp electron dng chung: Lin kt n, lin kt bi. * S xen ph cc AO Khi gp chung electron cc AO cha cc electron gp chung xen ph vi nhau - Xen ph trc: s-s, s-p, p-p - Xen ph bn: p-p * Lin kt , . - Xen ph trc to ra vng xen ph ln nn lin kt to thnh bn vng k hiu l . Cc nguyn t c th quay quanh trc lin kt. - Xen ph bn to ra vng xen ph nh hn li nm hai bn ng ni tm 2 nguyn t lin kt, nn n l b phn cng nhc, km bn. * Lin kt n, lin kt bi. - S cp electron dng chung bng 1 th to lin kt n . 2. S lai ha * K/n: L s t hp trn ln 1 s AO trong nguyn t to ra trng y AO lai ha ging nhau (c hnh dng v nng lng nh nhau) nhng nh hng khc nhau trong khng gian. * iu kin: Cc AO phi gn nhau v c nng lng tng ng nhau (thng nm trong cng mt lp electron) Cc nguyn t thuc chu k 2 lai ha hiu qu nht do kch thc ca cc AO b. * c im ca cc AO lai ha: - S cc AO lai ha bng s cc AO tham gia lai ha. - Cc AO lai ha c cng hnh dng, nng lng nhng khc nhau v s nh hng trong khng gian. V vy chng to ra cc lin kt ging nhau.

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Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

- Cc AO lai ha c mt phn m (tham gia xen ph to thnh lin kt), mt phn thu hp. - Cc AO lai ha ch tham gia xen ph trc. * Mt s kiu lai ha thng gp + Lai ha sp3: - Ch to lin kt n. - Phn t c th dng, t din u(4 nguyn t), t din lch(4 nguyn t), chp tam gic(4 nguyn t), gc(3 nguyn t). + Lai ha sp2: - C th to lin kt n hoc lin kt i. - Phn t c th dng tam gic u (4 nguyn t), gc (3 nguyn t) + Lai ha sp: - C th to lin kt n lin kt i, lin kt ba. - Phn t c dng ng thng. 3. c im ca lin kt CHT. a. Nng lng lin kt CHT. Nng lng phn li lin kt: l nng lng cn thit ph v lin kt thnh cc nguyn t t do. b. di lin kt CHT. - L khong cch gia 2 ht nhn ca 2 nguyn t tham gia lin kt. - di lin kt ph thuc vo bn cht nguyn t, trng thi lai ha, bi lin kt. - di cng ngn lin kt cng bn. c. Gc lin kt - L gc gia 2 lin kt ca cng mt nguyn t. - Gc lin kt ph thuc vo trng thi ca nguyn t (lai ha kiu no hay khng lai ha) d. Mmen lng cc. - Lin kt CHT phn cc khi 2 nguyn t c m in khc nhau lin kt vi nhau. Khi cp electron dng chung b lch v pha nguyn t c m in ln hn,nguyn t mang mt phn in tch m (-), nguyn t cn li b mt mt phn electron nn mang mt phn in tch dng (+). Gia 2 nguyn t xut hin mt lng cc c ln q(in tch ca lng cc). Khong cch gia 2 ht nhn nguyn t l khong cch ca lng cc: l(A0) Moomen lng cc c trng cho ln ca lng cc: =l.q - Theo thang Paolinh A B = A B T c th xc nh % ion ca lin kt A-B theo biu thc = 3,5 2 + 1,6 e. phn cc ha. - Khi cng ln lin kt cng phn cc. - Kh nng b phn cc ha (lm bin dng m my electron) di tc ng ca in trng bn ngoi. - Kh nng b phn cc ha tng theo chiu tng ca bn knh nguyn t (trong mt nhm A) - Kh nng b phn cc ha gim dn t tri sang phi trong mt chu k (do bn knh gim) - Kh nng b phn cc ha ca lin kt > (do lin kt nm hai bn ht nhn) - Kh nng b phn cc ha ca nguyn t trung ha ln hn ion dng (+), nhng nh hn ion m tng ng (do nh hng ca bn knh v s electron lp ngoi cng) VD: Xt cc HX T FI, bn knh nguyn t tng kh nng b phn cc ha tng bn lin kt gimkh nng phn li tngtnh axit tng (ngc chiu so vi phn cc ca lin kt). B. MT S LOI LIN KT YU. I. Lin kt hidro. 1. Khi nim. - L lin kt c hnh thnh do lc ht tnh in gia H mang mt phn in tch dng vi nguyn t mang mt phn in tch m c m in ln v cn cp electron cha tham gia lin kt (thc cht l mt dng xen ph AO trng ca H vi AO c cp electron cha tham gia lin kt) - K hiu: Lin kt H c biu din bng 3 du chm

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Trng THPT Chuyn Bc Ninh Vn Bnh

X-HY (X, Y l nguyn t c m in ln) VD: O H H H

Th/s Ng

... ..H .... . O

O H

H 2. iu kin hnh thnh lin kt hidro. * Lin kt H lin phn t. Hai phn t c 2 yu t - C nguyn t H linh ng: l H lin kt vi O, N, F - C nguyn t m in ln v cn cp electron cha tham gia lin kt: O, F, N, * Lin kt H ni phn t. Trong phn t c ng thi - C nguyn t H linh ng: l H lin kt vi O, N, F - C nguyn t m in ln v cn cp electron cha tham gia lin kt: O, F, N, - Lin kt H to thnh vng 5, 6 cnh bn VD: C2H4(OH)2 3. bn ca lin kt H. R-X-H...Y-R - H cng linh ng lin kt H cng bn, mun vy X phi c m in cng ln, mt electron cng nh (R ht electron th lm gim mt electron ca X, ngc li th lm tng mt electron) - Y c m in cng ln, mt electron ln th lin kt cng bn (R l nhm th y electron th lm tng mt electron ca R, ngc li th lm gim mt electron ca R). VD: Biu din cc kin lin kt H lin phn t c trong ru ung (dung dch ca etanol vi nc). Loi lin kt H no bn nht? 4. nh hng ca lin kt H n tnh cht vt l ca cht. a. nh hng n nhit si. - Cht c lin kt H lin phn t c nhit si cao hn cht c khi lng phn t tng ng hoc ln hn nhng khng c lin kt H lin phn t. - Lin kt H ni phn t lm cho phn t c dng cu nn lm gim nhit si ca phn t. - Lin kt H cng bn hoc cng nhiu lin kt H th nhit si cng tng. VD: C2H4(OH)2 > C2H5OH > C2H5NH2 b. nh hng n tan vo nc. Cht c kh nng to lin kt H vi nc tan nhiu trong nc. II. Lin kt Vandervan. - C bn cht tnh in v l lin kt yu. Lin kt Vandervan c hnh thnh do lc ht gia cc lng cc (phn t phn cc) hay cc lng cc tm thi (phn t khng phn cc) - Lc Vandervan gim nhanh theo khong cch gia cc lng cc q .q F = 1 2 (n > 2) rn - Lc Vandervan bao gm + Tng tc lng cc-lng cc (tng tc nh hng) + Tng tc lng cc-lng cc cm ng (tng tc cm ng). + Tng tc lng cc cm ng-lng cc cm ng (tng tc khuch tn). 1. Tng tc nh hng. - Phn t cha cc lin kt CHT phn cc nhng khng b trit tiu s hnh thnh mt lng cc. Cc lng cc c sp xp sao cho cc u tri du ht nhau vi lc ht F. VD: So snh nhit si cc ng phn ca 1,2-icloeten(dng cis c = 1,89, dng trans c = 0) 2. Tng tc cm ng. - Di tc dng ca mt in trng (c to nn do mt phn t phn cc hay mt ion), cc phn t khng phn cc b phn cc tm thi to thnh lng cc cm ng. Lc ht gia lng cc cm ng vi lng cc c nh gi l tng tc cm ng (cch tnh lc tng t tng tc nh hng). 3. Tng tc khuch tn.

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Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

- Cc phn t khng phn cc ti mt thi im no trng tm ca in tch m khc in tch dng lm cho phn t c lng cc cm ng tm thi, lng cc ny tc ng n cc electron ca cc nguyn t khc lm cho mt thi im nht nh tt c cc phn t khng phn cc u c th tr thnh lng cc cm ng. Tng tc gia cc lng cc cm ng gi l tng tc khuch tn. - ln ca tng tc khuch tn ph thuc vo khi lng phn t, kh nng phn cc ha. + Khi lng phn t tng tng tc khuch tn tng. + Kh nng phn cc ha tng tng tc khuch tn tng. - Mi cht u c tng tc khuch tn, nhng i vi cht phn cc v ion th tng tc ny qu b nn b qua. III. nh hng ca hnh dng phn t n nhit nng chy v nhit si. * dng tinh th, phn t no c kh nng sp xp c kht nht (dng cu) th phn t s c nhit nng chy cao. * trng thi lng, cc phn t chuyn ng hn lon, khi cc phn t c tng tc lin phn t cng ln (b mt tip xc ln) th nhit si cng cao. C. HIU NG CU TRC. I. Hiu ng cm ng I. 1. S phn cc ca lin kt . Trong lin kt cc electron dng chung b lch v pha nguyn t c m in cao hn. 2. Hiu ng cm ng I. CH3 > CH2 >> CH2 >>> Cl + K/n: Hiu ng cm ng l s chuyn dch mt electron dc theo mch lin kt trong phn t gy ra do s chnh lch v m in. + Hiu ng cm ng m (- I) gy ra bi nguyn t, nhm nguyn t ht electron v pha mnh - Ion dng ht electron mnh hn cc nhm khng mang in tch. - Hiu ng I tng theo m in: -I<-Br<-NH2<-OH<Cl<F<NO2 - Ph thuc vo trng thi lai ha: sp3 < sp2 < sp -CH=CH2 < -C6H5 < -C CH < -C N + Hiu ng cm ng dng (+I): gy ra bi cc nhm nguyn t y electron thng l cc nhm ankyl CnH2n+1- Hiu ng +I tng theo di ca mch, bc ca gc v s phn nhnh VD: so snh hiu ng +I ca cc gc butyl + c im ca hiu ng I: gim rt nhanh theo chiu di ca mch cacbon VD: So snh tnh axit ca cc cht sau CH3CH2CHClCOOH(1); CH2ClCH2CH2COOH(2); CH3CH2CHFCOOH(3); CH3CHClCH2COOH(4) II. Hiu ng lin hp C. 1. S phn cc ca cc lin kt . Trong lin kt s phn cc cng xy ra tng t lin kt . 2. Hiu ng lin hp C. * H lin hp l h gm cc electron v electron p (cp electron t do cha tham gia lin kt) cch nhau mt lin kt VD: H : CH2=CH-CH=CH2 H p: CH2=CH-Cl * K/n: Hiu ng lin hp l s chuyn dch mt electron hay electron p trong h lin hp v pha nguyn t c m in ln hn hay v pha h ca cc electron p. VD: CH2=CH-CH=O CH2=CH-Cl * Hiu ng lin hp m (-C) gy ra bi cc nhm c m in ln hay nhm mang in tch dng, c AO trng -C=O > -C=NH >> -C=CH2 -NO2 > -COOH > - CHO > -COR

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Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

* Hiu ng lin hp dng (+C) gy ra bi cc nhm y electron v pha lin kt i, l cc nguyn t c mt hay nhiu cp electron cha tham gia lin kt, cc electron ny linh ng d b ht v pha lin kt i. -NH2 > -OH > F - F > -Cl > -Br > -I * c im: Hiu ng cm ng t thay i theo chiu di mch C Ch : + i vi cc nhm c hiu ng lin hp lun c hiu ng I i km (thng l hiu ng I). - Nu c + C > -I th nhm c tnh cht y electron(-OH, -OR, -NH2, -NHR..) VD: (-)CH2=CH-OR - Nu c + C < -I th nhm c tnh cht ht electron(cc helogen). VD: (+)CH2=CH(++)-Cl - Nu c C, -I th nhm c tnh cht ht electron mnh + i vi vng benzen hiu ng lin hp ch tc dng trn h lin hp phng, v vy nhm nguyn t no gy cn tr tnh ng phng ca h s lm gim hiu ng lin hp. VD: nh hng ca hiu ng ortho III. Hiu ng siu lin hp H. - Cc lin kt C-H v tr lin hp vi lin kt
H-C-C=C Cc lin kt C-H y electron v pha lin kt i cc lin kt C-H c hiu ng siu lin hp dng (+H) - Cc lin kt C-F v tr lin hp vi lin kt

F-C-C=C Cc lin kt C-F ht electron v pha mnh nn c hiu ng siu lin hp m (-H) VD: So snh bn ca cc gc CH3. ; CH3-CH2. ; (CH3)2CH. ; CH3CH2CH2. IV. Hiu ng khng gian. 1. Hiu ng khng gian loi 1. -K/n: l hiu ng ca nhng nhm th c kch thc tng i ln, chim nhng khong khng gian ng k, do cn tr hay hn ch khng cho mt nhm chc no ca phn t tng tc vi phn t hay ion khc. VD: o,o-ddiissopropylstiren tc dng vi Br2 2. Hiu ng khng gian loi 2. - K/n: L hiu ng ca nhng nhm th c kch thc ln vi phm tnh song song ca trc cc m my electron v n trong h lin hp VD: So snh tnh axit ca p-nitrophenol v o,o-imetyl-p-nitrophenol

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Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

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Trng THPT Chuyn Bc Ninh Vn Bnh

TIT 7 PHN NG HU C

Th/s Ng

I. Phn loi phn ng hu c. 1. Phn ng th. S: Subsitution Phn loi theo tc nhn gm: SR; SE; SN(SN, SN2) VD: CH3-H + Cl-Cl CH3-Cl + HCl :SR C6H5-H + Br-Br C6H5-Br + HBr : SE C2H5-Cl + NaOH C2H5OH + NaCl : SN * K/n: Phn ng th l phn ng trong nguyn t (nhm nguyn t) ny thay th cho nguyn t (nhm nguyn t) khc. 2. Phn ng cng. A: Addition. VD: CH2 =CH2 + H-H CH3-CH3 * K/n: l phn ng trong 2 hay nghiu phn t hp cht hu c kt hp vi nhau m khng tch ra mt phn t no 3. Phn ng tch. E : Elimination VD: CH3-CH2OH CH2=CH2 + H2O CH3-CH2Cl CH2=CH2 + HCl * K/n: Phn ng tch l phn ng trong 2 nguyn t hay nhm nguyn t b tch ra khi 1 phn t m khng c nguyn t hay nhm nguyn t no thay th. II. Cc loi phn ct lin kt CHT. Nx: 1. Phn ct ng li gc t do. VD: Cl2 2Cl. Cl. + CH3-H CH3Cl + HCl * K/n: Phn ct ng li l s phn ct lin kt CHT sao cho cp electron chung c chia u cho 2 nguyn t c tham gia lin kt. * K/n gc t do: l nhng tiu phn cha mt electron c thn. c im ca gc t do: rt khng bn, thi gian tn ti ngn, c kh nng phn ng cao. Gc t do cng bn khi electron c thn c gii ta nh hiu ng lin hp, siu lin hp hoc hiu ng cm ng. VD: So snh bn ca cc gc t do sau a/ CH3. ; CH3CH2. ; (CH3)3C. ; (CH3)2CH. b/ CH2=CH-CH2. ; C6H5CH2. ; CH3-CH2-CH2. * Ch : gc t do cng bn kh nng to sn phm tng ng v gc t do cng d dng sn phm chim u th. VD: CH3CH2CH3 + Br2 sn phm chnh(> 90%), ph (< 10%) 2. Phn ct di li cacbocation, cacboanion. (CH3)3CBr 2-brom-2-metylpropan (C6H5)3C-H + Na H2 + Na+
H+

(CH3)3C+ + HBr cacbocation

+ (C6H5)3CCacboanion * K/n: Phn ct di li l s phn ct lin kt CHT phn cc trong nguyn t c m in cao chim hn cp electron chung tr thnh tiu phn mang in tch m, nguyn t cn li mn in tch dng. - in tch dng nm trn nguyn t C cacbocation - in tch m nm trn nguyn t C cacboanion * c im ca cacbocation v cacboanion: u khng bn, thi gian tn ti ngn v ch l tiu phn trung gian trong cc phn ng ha hc hu c. bn ca chng ph thuc vo cu trc: nhng yu t hiu ng lm gii ta in tch nguyn t C s lm tng bn ca chng. VD: CH3CH2+ < (CH3)2CH+ < (CH3)3C+ < CH2=CH-CH2+ < C6H5CH2+

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Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

CH3CH2CH2- < CH2=CH-CH2- < C6H5-CH2Tng t nh gc t do, nu gc cacbocation v cacboanion cng bn th xc sut chuyn ha thnh sn phm cng ln. III. Tc nhn electrophin v nucleophin. Nx: Tc nhn phn l cc hp cht hu c n gin hay cc hp cht v c. 1. Tc nhn electrophin (E+). - L nhng tc nhn c i lc vi electron. - Tc nhn electron bao gm: + cc ion dng: cacbocation; Br+; NO2+; H3O+. Nhng tiu phn c hiu ng lm tng mt in tch dng s lm tng mnh ca tc nhn electron. + cc phn t cha nguyn t thiu ht electron do s phn cc mnh ca cc lin kt nh SO3, AlCl3, FeCl3. 2. Tc nhn nucleophin (N:Nu) - L nhng tiu phn (c nhiu electron ) c i lc vi ht nhn nguyn t - Tc nhn nucleophin bao gm: + Cc ion m: cacboanion, OH-, Br-. + Cc phn t cha nguyn t cn cp electron cha tham gia lin kt: H2O; NH3; ROH; RNH2 (cc tiu phn nucleophin c cc nhm th lm tng mt electron th s lm tng mnh ca tc nhn nucleophin ) IV. Tc phn ng v nng lng hot ha. 1. Tc phn ng. 2. Nng lng hot ha. * K/n: L nng lng cn cung cp phn t chuyn ln trng thi chuyn tip c nng lng cao nht Ttct Ea Ea ttct

H cht u H <0 H cht cui Tin trnh phn ng Phn ng ta nhit Ttct1 Ttct2 Ea Sp trung gian H cht u H <0

H >0 H sn phm

H cht u Tin trnh phn ng Phn ng thu nhit

H cht cui Tin trnh phn ng

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Trng THPT Chuyn Bc Ninh Vn Bnh

Th/s Ng

Gin nng lng ca phn ng Hng s tc phn ng v nng lng hot ha: k = e-Ea/RT V. Khi nim v c ch phn ng. * K/n: C ch phn ng l ton b cc bc xy ra ni tip nhau dn ti sn phm, hay l con ng chi tit m h cc cht phi i qua to ra sn phm. S phn ct ng li thng hay dn ti cc phn ng theo c ch gc t do

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