BI TP CHN LC V DANH PHP V LP TH CA HIROCACBON VNG NO 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.

Monoxicloankan c cng thc chung l CnH2n (n 3). Lu : Trong chng trnh ha hc ph thng, xicloankan c hiu l bixiclo[2.2.1]heptan monoxicloankan. Bi 2. Vit cng thc phn t v c tn theo IUPAC cho cc xicloankan sau:
(a) (b)

(c)

(d)

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

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

(e)

(f)

(b) xiclopropan (a) xiclobutan (b)

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

(a) metylxiclopropan

(b)

(d)

1,2-dimetylxiclobutan

xiclopentan (c)

(d)

xiclohexan

(e)

(c) (e) (f)

(f)

(d)

xicloheptan 1,1-dimetylxiclopentan (g) (h)

Bi 4. Cho bit cng thc chung ca hirocacbon c hai vng no, phn loi. Cho bit nguyn tc c tn ca cc loi (e) 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 (g) lm mch

1,2,4-trimetylxiclohexan xiclooctan

(f)

1-isopropyl-2-metylxicloheptan

1-sec-butyl-2-etylxiclooctan

(h)

metylenxiclohexan

1-metyl-3-metylencyclopentan

chnh, cn vng nh lm nhm th. V d: 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

xiclopentylxiclohexan

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: Hai vng c chung cu ni, kiu bixiclo 5 8 Mch cacbon c nh s bt 3 u t mt nguyn t chung ( 4 9 10 mt nh), n cc nguyn t ca cu ni di nht, tip n spiro[4.5]decan 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: Bi 5. Hy gi tn cho cc hp cht sau.
9 8 7 6 1 2 3 2 1 6 6

(a)

(b)
5

bixiclo[4.3.0]nonan

(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:

Bi gii

(a)

(b) (b)
(a) bixiclo[2.1.1]hexan (d) (b)

Bi 7. Gi tn cc hp (a) cht sau:

bixiclo[1.1.1]pentan (c) (c) bixiclo[2.2.1]heptan (e) (e) bixiclo[3.1.1]heptan

Bi gii:

(d)

(c)

(d)

bixiclo[2.2.2]octan (f) (f)

(e) (f)

bixiclo[4.1.1]octan (b) (d) (f) spiro[2.3]hexan spiro[3.4]octan spiro[2.5]octan

(d) 5-etylspiro[3.4]octan (f) 8-ipropylspiro[4.5]decan (b) 1-metylspiro[2.3]hexan
2 3 4 5 6

(a) (c) (e) Bi 8. Cho bit cng thc spiro[2.2]pentan

cu to ca cc cht c tn sau:

spiro[2.4]heptan spiro[4.5]decan

(a) spiro[2,3]hexan

(b) 1-metylspiro[2.3]hexan (c) spiro[3.4]octan (e) spiro[4.5]decan Bi gii (a) spiro[2,3]hexan

(c) spiro[3.4]octan (d) etylspiro[3.4]octan (e) spiro[4.5]decan

5-

spiro[2.3]hexan 1-metylspiro[2.3]hexane
(f) 8-ipropylspiro[4.5]decan
7 6 5 3 4 spiro[4.5]decan 9 10 1 2

spiro[3.4]octan

Bi 9. V cng thc cu to ca cc hirocacbon hai vng no sau:

8-ipropylspiro[4.5]decan
(d) Bixiclo[3.3.0]octan Bi gii

(a) Bixiclo[2.2.1]heptan (b) Bixiclo[5.2.0]nonan (c) Bixiclo[3.1.1]heptan

5-etylspiro[3.4]octan

Bi 10. Cho bit cng thc cu to ca cc (a) cht c cng thc sau:

(b) bixiclo[2.2.1]heptan
(a) bixiclob utan (b) 2-

bixiclo[5.2.0]nonan

(c) bixiclo[3.1.1]heptan
metylbixiclobutan (c) bixiclo[3.2.1]octan (d) 8-metylbixiclo[3.2.1]octan Bi gii (a) Bixiclobutan

(d) bixiclo[3,3,0]octan

(b) 2-metylbixiclobutan
1 2 3

bixiclo[1.1.0]butan 2-metylbixiclo[1.1.0]butan
Bi 11. c tn cc cht sau:

(c) bixiclo[3.2.1]octan (d) metylbixiclo[3.2.1]octan

1 8 7

82 3 6

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

5 4 bixiclo[3.2.1]octan 8-metylbixiclo[3.2.1]octan

(a)

(b)

(c)

(d)

Bi 12. Xicloankan cis-1,2-dimetylxiclohexan no c ng phn cis trans-1,4-dimethylcyclohexan 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

cis-1,3-dimetylxiclohexan trans-1-etyl-3-mehylxiclopentae

CH3
(b) Etylxiclopantan. Khng c ng phn cis-trans.

CH3 H3C

CH 3 CH 3 CH3

H 3C

CH3

C2H5 C2H5 cis-1,3-dimetylxiclopentan

trans-1,3-dimetylxyclopentan

Hai cht trn l mt. (c) 1-etyl-2-metylxiclobutan: C ng phn cis-trans Bi 13. Hai hp cht hu c A v B u c cng thc phn t C5H10. C hai u HC C H CH khng phn ng vi Cl2 trong H 2H 2H5 H CC 33 2H 55 ti v lnh. A phn ng vi Cl2 c nh sng, nhng cho mt sn phm duy nht l -1-etyl-2-metylxiclobutan trans -1-etyl-2-metylxiclobutan C5H9Cl. Cn hp cht B cng cis tc dng vi Cl2 trong cng iu kin nhng cho 6 ng phn C5H9Cl 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 B tc dng vi Cl2 + (nh sng) tao ra 6 dn xut monoclo, nn B phi l metylxiclobutan.
Cl2 as Cl + HCl

CH CH 33

HC2H5

CH2Cl

CH3 Cl

CH3

CH3

Cl2 -HCl CH3 Cl

Cl CH3

CH3

Cl Cl

Bi 14. Hy cho bit ti sao 2,3-di-tert-butylbuta-1,3-dien khng th hin tnh cht ca 1 dien ( cng Br 2 lun cho sn phm 1,2 bt k nhit no) Bi gii Nu cht cho c s lin hp, bt buc 2 lin kt C-t-Bu phi cng mt mt phng. Tuy nhin, 2 nhm t-Bu cng knh, s ng phng ca 2 lin kt trn s khin 2 nhm t-Bu y nhau mnh, lm "xon" lin kt C-C gia 2 ni i, lm cho 2 mt phng ca ni i lch nhau, s lin hp khng tn ti. Bi 15. Gii thch ti sao khi cng nc vo allen thu c axeton thay v allyl ancol? Bi gii Trong phn t Alen c 2 C lai ho Sp2 v 1 C lai ho Sp. Khi proton ha trung tm cacbon lai ha sp nguyn t

cacbon ny to ra 1 allyl cation ging nh 1 cacbocation. Ta li thy cacbocation ny c obitan p trng ca cacbon mu th nh hng ban u 90o ri xoay n 180o c th lin hp vi ni i nhng do hiu ng cm ng ca lin kt i gn k lm tng nng lng ca lin kt chuyn i. Km bn hn khi cabocation gia (c lm bn bi hiu ng siu lin hp). 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
2 quanh trc i xng Cn mt gc sao cho phn Lu : Khi thc hin php quay phn t xung = t trng vi chnh n. Trc quay Cn gi l trc n 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 0 th nng thp nht. Nguyn nhn dn n s khc nhau v bn gia hai dng gh v thuyn l lc A 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. Hn na nguyn t H C1 v C4 ch cch nhau 1,84 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 emetylxiclohexan bn hn ametylxiclohexan. nhit thng e-metylxiclohexan chim 95% cn ametylxiclohexan chim 5%. a-metylxiclohexan km bn v c n hai tng tc syn, trong kho emetylxiclohexan khng c tng tc syn no c.

e-metylxiclohexan Bi 21. Xt cu dng sau:

5 4 3 6 1 2

a-metylxiclohexan

(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

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

CH3 CH3
1

H3C

(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

Bi 22. Xc nh cu trc bn trong mi cp

H3C

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 Bi 24. So snh tnh bn ca ng phn lp th 1,3,5- etylxiclopropan trimetylxiclohexan.

CH3
H H

808,8 kcal/mol H H

metylxiclobutan 801,2 kcal/mol

Bi gii CH CH 33 H 3C 3C Tt c nhm CH3 l equatorial trong H cis-1,3,5-trimetylxiclohexan nn n H3 C HH CH3 bn hn trans-1,3,5trimetylxiclohexan c cha mt nhm cis-1,3,5-trimetylxiclohexan trans -1,3,5-trimetylxiclohexan CH3 l axial.
H H H C 3 Bi 25. Vit cu trc phn t c cu dng bn nht cho H3C CH3 CH3 H 3C CH3 CH3 H H H HH CH3 H CH3 CH3 H H3C H cis-1,3,5-trimetylxiclohexan trans-1,3,5-trimetylxiclohexan
3

H HCH

mi hp cht sau: (a) trans-1-tertbutyl-3-metylxiclohexan (b) cis-1-tert-butyl3-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
(b) Trc tin v xiclohexan dng gh vi mt nhm tert-butyl v tr equatorial. to ra cis-1-tert-butyl-3metylxiclohexan th phi gn nhm metyl vo C-3 v tr equatorial. (c) trans-1-tert-butyl-4metylxiclohexan c hai nhm tert-butyl v C-4 metyl u l equatorial.

H C(CH3)3 CH3 C(CH3)3

H trans-1-tert-butyl-3-metylxiclohexan

H H C(CH3)3 H3C cis-1-tert-butyl-3-metylxiclohexan

(d) Ln na, nhm tert-butyl v tr equatorial, tuy nhin, trong cis-1tert-butyl-4-metylxiclohexan, C4-metyl phi v tr axial.

H H3C C(CH3)3

H
Bi 26. V cc ng phn v gi H C(CH3)3 tn ca hirocacbon c hai vng nhng khng cha nhm th ankyl c cng thc phn t CH3 C5H8. Bi gii cis-1-tert-butyl-4-metylxiclohexan

H trans-1-tert-butyl-4-metylxiclohexan

Bi 27. Vit cc ng phn v bixiclo[1.1.1]pentane bixiclo[2.1.0]pentan spiropentan gi tn ca hirocacbon c hai vng nhng khng cha nhm th ankyl c cng thc phn t C6H10 Bi gii Bi 28. Hy v mt m hnh phn t spiro[2.3]hexan cho nobonan

bixiclo[2,2,0]hexan

bixiclo[3,1,0]hexan

bixiclo[2,1,1]hexan

xiclopropylxiclopropan

(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 ?

Bi gii CH3 H Cu dng B bn H hn cu dng A v H3C H CH3 H3C c 2 CH3 H 1,3diaxial repulsions HH H trong khi cu (A) (B) 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

CH3

Bi 32. V cc cu dng gh ca trans-1,3-

(e) CH CH3 3 (e) CH3 (e)

b n h n

(e) CH3

CH3 (a)

(a) CH CH3 3 (a)

trans -1,2-dimetylxiclohexan cis-1,2-dimetylxiclohexan

Hai cu dng ny c b n nh nhau

dimetylxiclohexan v cis-1,3-dimetylxiclohexan. So snh bn ca cc cu dng .
CH3 (a)

Bi 33. V cc cu dng gh ca H3C (e) trans-1,4-

(e) CH3 CH (e)

3

H3C

(e)

b n h n

trans -1,3-dimetylxiclohexan cis -1,3-dimetylxiclohexan

(a) CH3

(a) CH (a) 3CH

3

Hai cu dng ny c b n nh nhau

dimetylxiclohexan v cis-1,4-dimetylxiclohexan. So snh bn ca cc cu dng. Bi gii
CH3 (a)

Bi 34. (a) 2- H C 3 Isopropyl-5CH3 (a)

(e)

CH3 (e) CH3 (e)

H3C

(e) (a) CH3 (a) CH3

b n h n

cis-1,4-dimetylxiclohexan trans-1,4-dimetylxiclohexan

Hai cu dng ny c b n nh nhau.

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

H H H3C CH3 H3C H

CH H 3
Cl CH3

Cl

CH3

H CH3

Cl C 2 H C bn cnh u tch c.

CH3

CH3

Cl CH3

Khng tch c v H C bn cnh khng ng ph ng v u vtrcisCH i 3 v i clo.

CH3

Cl Ch c 1 H l tch c.

CH3
CH3

Cl

CH3 Cl II

CH3 1,3 - imetylxiclohexen

1,3 - imetylxiclohexen

CH III CH3 3

(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

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

CH3 CH3

CH2

CH

CH2 CH3

CH3 CH3 CH2

C CH3 CH

CH2

CH H2C H2C

CH

CH

CH2 CH2 H2C

CH3 CH CH3

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

H2C
CH2

CH2

H C CH 2 2 CH3 C CH2
CH

H2C

CH3

CH3
- E tc dng chm vi Br2/CCl4, nn E l: - 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:

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
A: CH3 - CH2 - CH = CH2

CH3 C H

C:

CH3 C H C

H CH3

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.]