BI TP CHN LC V DANH PHP V LP TH CA HIROCACBON VNG NO ng Cng Anh Tun Trng THPT Chuyn L Qu n I. M U 1.

L do chn ti Chng ti chn ti Bi tp chn lc v danh php v lp th ca hirocacbon vng no vi nhng l do v mc ch sau y: Mt l cn c gio trnh dy hc sinh chuyn ha, ng thi thc hin nhim v nghin cu cc chuyn bi dng hc sinh gii m nh trng ra trong nm hc ny. Hai l, mng kin thc ny va l trng tm va l c s nghin cu nhng chuyn khc, nh hp cht t nhin, polime Ba l, thi hc sinh gii quc gia hin nay c nhiu bi ton lin n cu dng v danh php ca cc hp cht hu c. 2. Nhim v nghin cu Thit k, chn lc cc bi tp c h thng v danh php, cu hnh v cu dng ca hirocacbon vng no. 3. Phng php tin hnh Tp hp cc ti liu tham kho c lin quan n i tng nghin cu: Nghin cu c s l thuyt c lin quan. Lp s nghin cu:

Hirocacbon vng no Monoxicloankan Cng thc cu to Polixicloankan

Danh php

Cu hnh

Cu dng

Thit lp, chn lc cc bi tp ph hp vi mc tiu ra. II. NI DUNG Bi 1. Xicloankan l g? Th no l monoxicloankan? Th no l polixicloankan ? Cng thc chung ca monoxicloankan l g ? Bi gii Xicloankan l hirocacbon no mch vng. Xicloankan c mt vng (vng n) gi l monoxicloankan. V d:

Xicloankan c nhiu vng (a vng) gi l polixicloankan. V d: nobonan l mt bixicloankan.

bixiclo[2.2.1]heptan

Monoxicloankan c cng thc chung l CnH2n (n 3). Lu : Trong chng trnh ha hc ph thng, xicloankan c hiu l monoxicloankan. Bi 2. Vit cng thc phn t v c tn theo IUPAC cho cc xicloankan sau:
(a) (b)

(c)
(e)

(d)
(f)

Bi gii Qui tc c tn: Xiclo + tn mch chnh + an

(a) xiclopropan (b) xiclobutan

(c) xiclopentan

(d) xiclohexan

(e)

(f)

xicloheptan

xiclooctan

Bi 3. Vit cng thc phn t v c tn theo IUPAC cho cc xicloankan sau:

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

Bi gii Qui tc c tn: s ch v tr + tn nhnh + xiclo + tn mch chnh + an

(a) (b)

metylxiclopropan

1,2-dimetylxiclobutan

(c)

(d)

1,1-dimetylxiclopentan

1,2,4-trimetylxiclohexan

(e)

(f)

1-isopropyl-2-metylxicloheptan

1-sec-butyl-2-etylxiclooctan

(g)

(h)

metylenxiclohexan

1-metyl-3-metylencyclopentan

Bi 4. Cho bit cng thc chung ca hirocacbon c hai vng no, phn loi. Cho bit nguyn tc c tn ca cc loi ny. Bi gii Cng thc chung ca hirocacbon hai vng no l CnH2n-2 n 4. N c 3 loi, l: - Hai vng ri Ly vng ln lm mch chnh, cn vng nh lm nhm th. V d:

xiclopentylxiclohexan

Hai vng c chung mt nguyn t mt vng, kiu spiro. Mch cacbon c nh s ht vng nh n vng ln, bt u t mt nguyn t k nguyn t chung. Tn ca hiro kiu spiro gm cc b phn hp thnh theo trnh t sau y: spiro + [cc s nguyn t cacbon ring (t s ln n s nh)] + tn hirocacbon mch h tng ng. V d:
2 3 4 10 9 1 6 5 6 8

spiro[4.5]decan

Hai vng c chung cu ni, kiu bixiclo Mch cacbon c nh s bt u t mt nguyn t chung ( mt nh), n cc nguyn t ca cu ni di nht, tip n cc cu ni ngn hn. Tn ca hirocacbon kiu gm cc b phn hp thnh theo th t sau: bixiclo + [s nguyn t C cc cu ni (ghi t s ln n s nh)] + tn ca hirocacbon mch h tng ng. V d:
9 8 7 6 4 5 1 2 3

bixiclo[4.3.0]nonan

Bi 5. Hy gi tn cho cc hp cht sau.

(a) (b)

(c)

(d)

Bi gii
(a) xiclopropylxiclopentan (b) xiclobutylxiclobutan

(c) 1-xiclopentyl-4-metylcyclohexan

(d) (3-metylcyclopentyl)xiclohexan

Bi 6. Hy gi tn cc cht sau:

(a)

(b)

(c)

(d)

(e)
Bi gii
(a) bixiclo[1.1.1]pentan (c) bixiclo[2.2.1]heptan (e) bixiclo[3.1.1]heptan (b)

(f)

bixiclo[2.1.1]hexan (d) bixiclo[2.2.2]octan (f) bixiclo[4.1.1]octan

Bi 7. Gi tn cc hp cht sau:

(a)

(b)

(c)
(e)
Bi gii: (a)
spiro[2.2]pentan (b)

(d)
(f)

spiro[2.3]hexan

(c)

(d)

spiro[2.4]heptan

spiro[3.4]octan

(e)

(f)

spiro[4.5]decan spiro[2.5]octan Bi 8. Cho bit cng thc cu to ca cc cht c tn sau: (a) spiro[2,3]hexan (b) 1-metylspiro[2.3]hexan (c) spiro[3.4]octan (d) 5-etylspiro[3.4]octan (e) spiro[4.5]decan (f) 8-ipropylspiro[4.5]decan

 Bi gii (a) spiro[2,3]hexan

(b) 1-metylspiro[2.3]hexan
2 3 1 6 5 4

spiro[2.3]hexan (c) spiro[3.4]octan

1-metylspiro[2.3]hexane (d) 5-etylspiro[3.4]octan

spiro[3.4]octan (e) spiro[4.5]decan

5-etylspiro[3.4]octan

(f) 8-ipropylspiro[4.5]decan
7 8 6 5 3 9 10 4 1 2

spiro[4.5]decan

8-ipropylspiro[4.5]decan

Bi 9. V cng thc cu to ca cc hirocacbon hai vng no sau: (a) Bixiclo[2.2.1]heptan (b) Bixiclo[5.2.0]nonan (c) Bixiclo[3.1.1]heptan (d) Bixiclo[3.3.0]octan Bi gii

(a) bixiclo[2.2.1]heptan

(b)

bixiclo[5.2.0]nonan

(c)

(d)

bixiclo[3,3,0]octan bixiclo[3.1.1]heptan Bi 10.Cho bit cng thc cu to ca cc cht c cng thc sau: (a) bixiclobutan (b) 2-metylbixiclobutan (c) bixiclo[3.2.1]octan (d) 8-metylbixiclo[3.2.1]octan Bi gii (a) Bixiclobutan (b) 2-metylbixiclobutan
1 2 3 4

bixiclo[1.1.0]butan (c) bixiclo[3.2.1]octan

2-metylbixiclo[1.1.0]butan

(d) 8-metylbixiclo[3.2.1]octan

1 8 7

2 3 6

bixiclo[3.2.1]octan

8-metylbixiclo[3.2.1]octan

Bi 11.c tn cc cht sau:

(a)

(b)

(c)

(d)

Bi gii Ch : Hai nhm th cng pha l ng phn cis, cn khc pha l ng phn trans.

cis-1,2-dimetylxiclohexan

cis-1,3-dimetylxiclohexan

trans-1,4-dimethylcyclohexan

trans-1-etyl-3-mehylxiclopentae

Bi 12.Xicloankan no c ng phn cis trans ? Nu c v c hai ng phn . (a) 1,3-dimetylxiclopantan (b) Etylxiclopantan (c) 1-etyl-2-metylxiclobutan Bi gii (a) 1,3-dimetylxiclopantan. C ng phn cis trans CH3 CH3 H3C CH3
cis-1,3-dimetylxiclopentan CH3 H3C CH3

CH3

trans-1,3-dimetylxyclopentan (b) Etylxiclopantan. Khng c ng phn cis-trans. C2H5 C2H5

Hai cht trn l mt. (c) 1-etyl-2-metylxiclobutan: C ng phn cis-trans

CH3

C2H5

CH3

H3C

C2H5

C2H5

H3C

C2H5

cis-1-etyl-2-metylxiclobutan trans-1-etyl-2-metylxiclobutan Bi 13. Hai hp cht hu c A v B u c cng thc phn t C5H10. C hai u khng phn ng vi Cl2 trong ti v lnh. A phn ng vi Cl2 c nh sng, nhng cho mt sn phm duy nht l C5H9Cl. Cn hp cht B cng tc dng vi Cl2 trong cng iu kin nhng cho 6 ng phn C 5H9Cl khc nhau, c th phn bit bng phng php vt l. Hy xc nh cu trc ca A, B v cc sn phm monoclo . Bi gii: A v B c cng thc C5H10 nn chng c th l anken hoc xicloankan. Theo u bi, cc cht ny khng tc dng vi Cl2 ti v lnh nn A v B l cc xicloankan. A tc dng vi Cl2 cho mt monoclo duy nht nn A l xiclopentan

Cl2

as

Cl

HCl

B tc dng vi Cl2 (nh sng) tao ra 6 dn xut monoclo, nn B phi l metylxiclobutan. CH3 CH2Cl CH3 Cl Cl2 -HCl CH3 Cl Cl CH3

CH3

CH3

Cl Cl Bi 14.Sc cng Baeyer l g? Bi gii Xut pht t hai tin l cc vng no c cu trc phng v gc bnh thng ca hirocacbon no l 109028, nm 1885, Baeyer cho rng s o nh hay trng rng cc gc ca vng no u dn n mt sc cng l cho tnh bn ca vng gim i. Ngi ta gi l sc cng Baeyer. Sc cng cng ln, vng tng ng cng t bn. mnh ca sc cng c nh gi bng . c tnh theo cng thc

v d: n 3 4 5 6 7 8 9 0 0 0 0 0 0 24 44 9 44 0 44 -5 44 9 33 12 46 -15006 Bi 15.V sao ni lin kt C-C trong xilopropan c gi l lin kt qu chui ? Bi gii Xiclopropan l hp cht vng no duy nht c cu to phng. Theo quan nim hin i, phn xen ph cc i ca cc m my electron khng nm trn ng thng ni lin hai nguyn t cacbon m c s un cong. S un cong ny lm cho phn xen ph m my electron c gim i, nhng sp xp nh th c li v mt nng lng. Cc lin kt C-C ny c gi l lin kt qu chui, n mang tnh cht trung gian gia lin kt v bnh thng. Do s un cong nh vy, thc t gc lin kt ca vng ch bng 1060 ch khng phi 109028 v ln hn nhiu so vi gc cu to phng ca tam gic u (600). Xiclopropan rt d b m vng di tc dng ca hirohalogenua, Br2 v b hiro ho c cht xc tc.

( n 2) 180 1 0 109 28' 2 n

Bi 16.Th no l lc y Pitze? Bi gii Thc t, cc vng no (tr xiclopropan) khng phi l nhng vng phng. Trong mt vng ngoi sc cng gc Baeyer c c mt lc y na l lc y gia cc nguyn t hiro trng thi che khut mt phn hay ton phn gy nn, o mt vi nguyn cacbon ca vng b lch ra khi mt phng vng. Lc y gi l lc y Pitze Bi 17.Nguyn nhn no xiclobutan tn ti dng khng phng? Bi gii Theo quan nim hin nay, xiclobutan c cu to khng phng gc gp c gi tr khong 20-250. Tnh khng phng ca xiclobutan c chng t t cc d kin thc nghim ca gin Rnghen, gin electron, momen lng cc, ph cng hng t ht nhn v mt s phng php khc. Nguyn nhn ch yu xiclobutan tn ti dng khng phng l gim sc cng Pitz.

Bi 18.Xiclopentan tn ti hai cu dng khng phng: dng phong b v dng na gh. Hy v hai cu dng ny v cho bit dng no c tm i xng, dng no c trc i xng. Bi gii Nu gi s phn t xiclopentan nm trn mt mt phng th gc lch 0044, do coi nh khng c sc cng Baeyer. Nhng y 5 lin kt C-C dng che khut nn li xut hin sc cng Pitz. Thc t xiclopentan tn ti hai cu dng khng phng l cu dng phong b c mt phng i xng nn cn gi l cu dng Cs. Cu dng na gh c trc i xng bc hai nn cn gi l cu dng C2. C5 C2 Lu : Khi thc hin php quay phn t xung quanh trc i xng Cn mt gc =

2 sao cho phn t n

trng vi chnh n. Trc quay Cn gi l trc i xng cp n. Bi 19.Da vo gin th nng sau, cho bit cu dng no ca xiclohexan bn nht ? Gii thch ?

 Bi gii Cu dng gh bn hn cu dng thuyn, v n c th nng thp nht. Nguyn nhn dn n s khc nhau v bn gia hai dng gh v thuyn l lc y tng tc gia cc nguyn t hiro ca vng. dng gh tt c u c phn b theo hnh th xen k. Trong khi dng thuyn ch c 4 h thng (C1-C2, C3-C4, C4-C5 v C6-C1) l phn b xen k, cn hai h thng cn li C2-C3 v C5-C6) th phn b che khut. 0 Hn na nguyn t H C1 v C4 ch cch nhau 1,84 A nn n c mt lc y khong 3 kcal/mol. Tng cng th nng ca dng thuyn ln hn dng gh 6,8 kcal/mol.

Cng thc Newman dng gh Cng thc Newman dng thuyn Bi 20. Trong xiclohexan, xc inh lin kt trc (axial) v lin kt bin (equatorial). So snh tnh bn ca a-metylxiclohexan v e-metylxiclohexan. Gii thch. Bi gii Trong xiclohexan, sau nguyn t cacbon dng gh c phn b trn hai mt phng song song. Mt phng th nht cha C1, C3 v C5 ; mt phng th hai cha C2, C4 v C6. Trc i xng bc ba ca phn t thng gc vi hai mt phng. 12 lin kt C-H c chia lm hai nhm: nhm th nht gm 6 nguyn t H song song vi trc i xng bc ba ( 3 lin kt hng ln v 3 lin kt hng xung). Ta gi l lin kt trc, k hiu l a (axial). Nhm th hai gm 6 lin kt cn li, chng hng ra ngoi bin phn t (to vi trc i xng mt gc 1090 c gi l lin kt bin, k hiu l e (equatorial).

Kt qu kho st l thuyt cng nh thc nghim e-metylxiclohexan bn hn a-metylxiclohexan. nhit thng e-metylxiclohexan chim 95% cn a-metylxiclohexan chim 5%. a-metylxiclohexan km bn v c n hai tng tc syn, trong kho e-metylxiclohexan khng c tng tc syn no c.

e-metylxiclohexan Bi 21.Xt cu dng sau:

a-metylxiclohexan

5 4 3

1 2

(a) Nhm metyl gn pha di C-6 l lin kt trc (axial) hay lin kt bin (equatorial) ? (b) So snh bn khi nhm metyl gn pha di C-1 v C-4. (c) Khi nhm metyl gn vo C3 th to ra cu dng bn, vy n gn vo di hay trn? Bi gii (a) Nhm CH3 l lin kt trc (a)
6

CH3

(b) C-1 km bn hn C-4, v lin kt trc km bn hn lin kt bin (e).

CH3
1

H3C
4

(c) Nhm CH3 gn vo C-3 to ra cu dng bn th phi l lin kt bin, tng ng vi v tr ny l

gn vo pha di.
H

H3C

Bi 22. Xc nh cu trc bn trong mi cp cu dng cho di y?

 Bi gii: Cc cu dng bn l:

Bi 23.t chy hon ton etylxiclopropan v metylxiclobutan, so snh nng lng gii phng ca mi ng phn. Bi gii Etylxiclopropan v metylxiclobutan l ng phn (u c cng thc phn t C5H12). ng phn no bn gii phng nng lng thp. Etylxiclopropan c sc cng gc ln v km bn hn metylxiclobutan.

CH2CH3

CH3

metylxiclobutan etylxiclopropan 808,8 kcal/mol 801,2 kcal/mol Bi 24.So snh tnh bn ca ng phn lp th 1,3,5-trimetylxiclohexan. H H H H
H3C H CH3 CH3 H3C H3 C H CH3

cis-1,3,5-trimetylxiclohexan trans-1,3,5-trimetylxiclohexan

Bi gii Tt c nhm CH3 l equatorial trong cis-1,3,5-trimetylxiclohexan nn n bn hn trans-1,3,5trimetylxiclohexan c cha mt nhm CH3 l axial. H H CH3 CH3 H3C H3C CH3 H H H H CH3
H H3C H3C H cis-1,3,5-trimetylxiclohexan H CH3 H

CH3 H CH3

CH3 H

trans-1,3,5-trimetylxiclohexan Bi 25.Vit cu trc phn t c cu dng bn nht cho mi hp cht sau: (a) trans-1-tert-butyl-3-metylxiclohexan (b) cis-1-tert-butyl-3-metylxiclohexan (c) trans-1-tert-butyl-4-metylxiclohexan (d) cis-1-tert-butyl-4-metylxiclohexan Bi gii

(a) c ng phn cu dng bn nht th nhm tert-butyl l equatorial. Sau thm nhm CH3 (axial) vo C-3 ca vng xiclohexan.

H C(CH3)3 CH3

H C(CH3)3

H trans-1-tert-butyl-3-metylxiclohexan
(b) Trc tin v xiclohexan dng gh vi mt nhm tert-butyl v tr equatorial. to ra cis-1tert-butyl-3-metylxiclohexan th phi gn nhm metyl vo C-3 v tr equatorial. H H
C(CH3)3 H3C cis-1-tert-butyl-3-metylxiclohexan

(c) trans-1-tert-butyl-4-metylxiclohexan c hai nhm tert-butyl v C-4 metyl u l equatorial. H

H3C C(CH3)3

H trans-1-tert-butyl-4-metylxiclohexan (d) Ln na, nhm tert-butyl v tr equatorial, tuy nhin, trong cis-1-tert-butyl-4-metylxiclohexan, C4-metyl phi v tr axial. H H CH3 cis-1-tert-butyl-4-metylxiclohexan
Bi 26. V cc ng phn v gi tn ca hirocacbon c hai vng nhng khng cha nhm th ankyl c

C(CH3)3

cng thc phn t C5H8. Bi gii

spiropentan
cng thc phn t C6H10 Bi gii

bixiclo[2.1.0]pentan

bixiclo[1.1.1]pentane

Bi 27. Vit cc ng phn v gi tn ca hirocacbon c hai vng nhng khng cha nhm th ankyl c

spiro[2.3]hexan

bixiclo[2,2,0]hexan

bixiclo[3,1,0]hexan

xiclopropylxiclopropan bixiclo[2,1,1]hexan Bi 28.Hy v mt m hnh phn t cho nobonan (bixiclo[2,2,1]heptan). Vng 6 cnh dng thuyn hay gh? Hp cht monoclo nobonan c bao nhiu ng phn khc nhau? Bi gii nobonan

Vng 6 cnh ca nobonan dng thuyn. monoclo nobonan c 4 ng phn: Cl

Cl

Cl Cl A B C D A v B c th c ng phn quang hc Bi 29.Nhit t chy ca mt s xicloankan nh sau: Xicloankan Xicloankan H (kcal/mol) H (kcal/mol) Xiclopropan 499,83 Xiclonoan 1429,50 Xiclobutan 655,86 Xicloecan 1586,00 Xiclopentan 793,52 Xiclounecan 1742,40 Xiclohexan 944,48 Xicloecan 1892,40 Xicloheptan 1108,20 Xicltriecan 2051,40 Xiclooctan 1269,20 Xiclotetraecan 2203,60 Hy tnh nhit t chy ca nhm metylen trong mi xicloankan. Hy tnh sc cng gc trong cc xicloankan trn. Bit rng xiclohexan l tng trng cho h khng c sc cng gc (sc cng gc t do). Hy lit k cc loi sc cng gc trong cc vng c kch thc khc nhau. (b) Hy gii thch ti sao nhng vng c kch thc trung bnh (C7-C11) c tng hp vi hiu sut thp hn so vi vng nh (C3-C6) hoc vng ln (C12-Cn)? Bi gii (a) tnh nhit t chy ca mi nhm CH2 c trong cc xicloankan ta ly nhit t chy ca xicloankan chia cho s nguyn t C. Hexan c sc cng gc bng khng nn nhit t chy ca nhm CH2 khi khng c sc cng gc l 157,41 kcal/mol. T ta c th tnh c nhit t chy ca cc xicloankan tng ng khi khng c sc cng gc bng cch ly 157,41 nhn cho s nguyn t cacbon. Kt qu th hin trong bng sau. n Nhit t chy Nhit t chy ca Nhit t chy Sc cng gc kcal/mol CH2 kcal/mol khng c sc cng kcal/mol gc kcal/mol 499.83 3 166.61 472.24 27.59 655.86 4 163.97 629.65 26.21

793.52 5 158.7 787.07 6.45 944.48 6 157.41 944.48 0 1108.2 7 158.31 1101.89 6.31 1269.2 8 158.65 1259.31 9.89 1429.5 9 158.83 1416.72 12.78 1586 10 158.6 1574.13 11.87 1742.4 11 158.4 1731.55 10.85 1892.4 12 157.7 1888.96 3.44 2051.4 13 157.8 2046.37 5.03 2203.6 14 157.4 2203.79 -0.19 Nhn xt Sc cng gc gim dn t xiclopropan n xiclohexan. V c s kt hp sc cng gc (sc cng Bayer) v s y tng h gia cc nhm th v tr che khut (sc cng Pitzer). Cc vng ln n 12 sc cng gc nh khng ng k. Cc vng trung bnh (C7-C11) c sc cng gc. (b) Entropi nh hng n cu dng ca vng nh. Nhng vng ny c kh nng ng vng ln ngay c khi c sc cng. Nhng vng ln c th to ra vi hiu sut hp l v chng c sc cng gc b v yu t entropi c th vt qua bng s la chn iu kin phn ng ph hp. Cc vng trung bnh v mt entropi v sc cng u khng thun li nn hiu sut phn ng nh. Bi 30.So snh bn ca hai cu dng sau, gii thch ? H H CH CH
3 3

CH3 H3C HH (A) H H H3C

H CH3 H (B)

Bi gii Cu dng B bn hn cu dng A v c 2 CH3 H 1,3-diaxial repulsions trong khi cu dng A c mt CH3-CH3 1,3-diaxial repulsion v hai CH3-H 1,3-diaxial repulsion. Bi 31.V cc cu dng gh ca trans-1,2-dimetylxiclohexan v cis-1,2-dimetylxiclohexan. So snh bn ca cc cu dng . Bi gii
CH3 (a) CH3 (e) CH3

(e)

b h n n trans-1,2-dimetylxiclohexan
CH3 (e)

CH3 (a)

(e) CH3
CH3 (a) CH3 (a)

cis-1,2-dimetylxiclohexan Hai cu dng ny c b nh nhau n Bi 32.V cc cu dng gh ca trans-1,3-dimetylxiclohexan v cis-1,3-dimetylxiclohexan. So snh bn ca cc cu dng .

CH3 (a) CH3 (e) H3C

(e)

CH3 (a)

trans-1,3-dimetylxiclohexan Hai cu dng ny c b nh nhau n

CH3 (e) H3C (e)

b h n n

cis-1,3-dimetylxiclohexan

(a) CH3

(a) CH3

Bi 33. V cc cu dng gh ca trans-1,4-dimetylxiclohexan v cis-1,4-dimetylxiclohexan. So snh

bn ca cc cu dng. Bi gii
CH3 (a)

(e)
H3C CH3 (e)

b h n n
CH3 (e)

(a) CH3

trans-1,4-dimetylxiclohexan
H3C

(e)
CH3 (a)

(a) CH3

cis-1,4-dimetylxiclohexan Hai cu dng ny c b nh nhau. n Bi 34.(a) 2-Isopropyl-5-metylxiclohexanol c 4 ng phn cis trans, hy vit cc ng phn . (b) V cu dng ca cc ng phn . Trong s 4 ng phn ng phn no bn nht? Bi gii (a) Cng thc ca 4 ng phn

(b) Biu din cc cu dng

(c) Cu dng bn nht l trans-2-Isopropyl-cis-5-metylxiclohexanol. V tt c cc nhm th u dng e.

Bi 35.Gii thch ti sau 1,2-dimetylxiclohexan c ng phn hnh hc trong khi 1,2dimetylxiclododecan th khng ?

Di vng xiclododecan ln cc nhm nguyn t c th quay t do, v th n khng th tn ti ng phn cis-trans. Bi 36. Vit cng thc cc ng phn lp th khng i quang(ng phn lp th i - a ) ca 2 - clo - 1,3 imetylxiclohexan v cho bit cu trc sn phm to thnh khi cho cc ng phn tc dng vi CH3ONa. Bi gii
CH3 Cl CH3 CH3 Cl CH3 I II CH3 CH3 Cl III CH3 CH3 Cl

H H H3C CH3 H3C H

H Cl CH3

CH3

H CH3

Cl C 2 H C bn cnh u tch c. CH3

Khng tch c v C H bn cnh khng ph ng ng v u vtrcis v i clo. i

Cl Ch 1 H l tch c. c

CH3

CH3 1,3 - im etylxiclohexen

CH3 1,3 - imetylxiclohexen

Bi 37. Su hirocacbon A, B, C, D, E, F u c cng thc phn t C4H8. Cho tng cht vo brom trong

CCl4 khi khng chiu sng th thy A, B, C, D tc dng rt nhanh., E tc dng chm hn, cn F th hu nh khng phn ng. Cc sn phm thu c t B v C l nhng ng phn quang hc khng i quang(ng phn lp th i - a) ca nhau. Khi cho tc dng vi H2(Pd, t0) th A, B, C u cho cng mt sn phm G. B c nhit si cao hn C. 1. Xc nh cng thc ca 6 hirocacbon trn. Gii thch? 2. So snh nhit si ca E v F. 3. Nu c C, D, E, F. Hy nu phng php ho hc nhh bit chng. Bi gii. 1. Cc ng phn c th c ca C4H8:

CH3 CH3

CH2

CH

CH2 CH3

CH3 CH3 CH2

C CH3 CH

CH2

CH H2C

CH

CH CH3

CH2

H2C CH2 H2C CH CH3 - V F hu nh khng phn ng vi Br2/CCl4, nn F l:

H2C H2C

CH2 CH2

- E tc dng chm vi Br2/CCl4, nn E l:

CH2

H2C

CH

CH3

- V A, B, C c hiro ho u cho cng mt sn phm G chng t A, B, C c khung C nh nhau, nn cn li D:

CH3

CH2

CH3
V B, C tc dng vi Br2/CCl4 cho nhng ng phn quang hc khng i quang ca nhau(c t nht 2*C), nn B v C l ng phn cis - trans ca nhau. Do B c nhit si cao hn C nn B l ng phn cis (phn cc hn).

B: CH3 C H C

CH3 H

C:

CH3 C H C

H CH3

A: CH3 - CH2 - CH = CH2

III. KT LUN Nghin cu ti ny, chng ti thu c mt s kt qu sau: 1. Tng quan c l thuyt ca ti nghin cu. 2. Chng ti thit k v chn lc 37 bi tp v danh php v lp th ca hirocacbon vng no c li gii, trong : Bi tp v khi nim: 9 bi Bi tp v danh php: 9 bi Bi tp v cu hnh: 4 bi Bi tp v cu dng: 11 bi Bi tp tng hp: 4 bi 3. Xy dng c h thng bi tp t d n kh, t n gin n phc tp, gip cho cc em hc sinh d tip thu. ti ny l mt ti liu gip cc em hc sinh t hc, t nghin cu, l ti liu tham kho cho gio vin bi dng hc sinh gii cc cp. Kin ngh: Danh php v lp th ca cc hp cht khc, nh : hirocacbon khng no, hirocacbon thm v cc dn xut ca hirocacbon s tip tc nghin cu sau ny.

TI LIU THAM KHO ng nh Bch(2001), Nhng vn ha hc hu c, NXB Khoa hc v K thut Trnh nh Chnh (1995), C s l thuyt ha lp th, Ti liu BDTX. Trn Quc Sn, (1977), C s l thuyt ha hu c, NXB Gio dc. Trn Quc Sn Trn Th Tu (2003), Danh php hp cht hu c. Thi Don Tnh (2002) Gio trnh c s l thuyt ha hc, NXB Khoa hc v K thut. Nguyn Trng Th (2000), Olympic ha hc Vit Nam v Quc t, tp 3 Nhng bi tp chun b cho k thi Olympic quc t ln th 30, 31, 32, NXB Gio dc. [7.] Ng Th Thun (1999), Ha hc hu c, phn bi tp, NXB Khoa hc v K Thut. [8.] Nguyn nh Triu (2003), 2000 Cu hi v bi tp trc nghim ha hc hu c, Tp 1, NXB Khoa hc v K Thut. [9.] Francis A. Carey (1996), Organic Chemistry, The McGraw-Hill [10.] Robert Thormnton Morrison (1992), Organic Chemistry, Prentice Hall. [11.] http://depts.washington.edu/chemcrs/bulkdisk/chem237B_aut06/handout_Chapter_3_CHEM237B aut06.pdf [12.] http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch03/ch3-0.html [13.] http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch03/ch3-0.html [14.] http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch03/ch3-0.html [15.] http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch03/ch3-0.html [16.] http://www.columbia.edu/itc/chemistry/chem-c3045/organic/text_chapters/ch3.html [17.] http://www.chem.uic.edu/web1/OCOL-II/WIN/ALKANE/F3.HTM [18.] http://stezlab1.unl.edu/Chem251-2005/PowerPoint/JJSChapter%203.ppt [19.] http://www.cem.msu.edu/~parrill/movies/conf.html [20.] http://www.chemistry.mcmaster.ca/courses/2oa3/lecture_two.pdf [21.] http://www.chemistry.mcmaster.ca/courses/2oa3/lecture_two.pdf [22.] http://chemistry.uca.edu/faculty/manion/2401/2401res/chap4.pdf [1.] [2.] [3.] [4.] [5.] [6.]