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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:
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:
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)
(c) xiclopentan
(d) xiclohexan
(e)
(f)
xicloheptan
xiclooctan
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
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
(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)
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
(b) 1-metylspiro[2.3]hexan
2 3 1 6 5 4
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
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
(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
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.
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 =
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.
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
H3C
4
gn vo pha di.
H
H3C
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
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
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
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
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 .
(e)
CH3 (a)
b h n n
cis-1,3-dimetylxiclohexan
(a) CH3
(a) CH3
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
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 Cl CH3
CH3
H CH3
Cl Ch 1 H l tch c. c
CH3
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
C CH3 CH
CH2
CH H2C
CH
CH CH3
CH2
H2C H2C
CH2 CH2
CH2
H2C
CH
CH3
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
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.]