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:
















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:

Monoxicloankan
Polixicloankan
Cng thc
cu to
Danh php Cu hnh
Cu dng
Hirocacbon
vng no

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 C
n
H
2n
(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) (d)

(e)
(f)

Bi gii Qui tc c tn: Xiclo + tn mch chnh + an
(a) (b)
(c) (d)
(e)
(f)
xiclopropan xiclobutan
xiclopentan
xiclohexan
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)
(c) (d)
(e)
(f)
metylxiclopropan 1,2-dimetylxiclobutan
1,1-dimetylxiclopentan 1,2,4-trimetylxiclohexan
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 C
n
H
2n-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:
1
2
3
4
5
6 6
8
9 10
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:
bixiclo[4.3.0]nonan
1
2
3
4
5
6
7
8
9

Bi 5. Hy gi tn cho cc hp cht sau.
(a)
(b)
(c)
(d)

Bi gii
(a)
(b)
(c)
(d)
xiclopropylxiclopentan
xiclobutylxiclobutan
1-xiclopentyl-4-metylcyclohexan (3-metylcyclopentyl)xiclohexan

Bi 6. Hy gi tn cc cht sau:
(a) (b)
(c)
(d)
(e) (f)

Bi gii
(a) (b)
(c)
(d)
(e) (f)
bixiclo[1.1.1]pentan bixiclo[2.1.1]hexan
bixiclo[2.2.1]heptan bixiclo[2.2.2]octan
bixiclo[3.1.1]heptan bixiclo[4.1.1]octan

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

(c)
(d)

(e) (f)

Bi gii:
(a) (b)
spiro[2.3]hexan spiro[2.2]pentan

(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

spiro[2.3]hexan

1-metylspiro[2.3]hexane
1
2
3
4
5
6

(c) spiro[3.4]octan (d) 5-etylspiro[3.4]octan
spiro[3.4]octan

5-etylspiro[3.4]octan

(e) spiro[4.5]decan (f) 8-ipropylspiro[4.5]decan
spiro[4.5]decan

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

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

bixiclo[2.2.1]heptan
(a)
bixiclo[5.2.0]nonan
(b)
bixiclo[3.1.1]heptan
(c) (d)
bixiclo[3,3,0]octan

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

bixiclo[1.1.0]butan

2-metylbixiclo[1.1.0]butan
1
2
3
4

(c) bixiclo[3.2.1]octan (d) 8-metylbixiclo[3.2.1]octan
bixiclo[3.2.1]octan

8-metylbixiclo[3.2.1]octan
1
2
3
4 5
6
7
8

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
CH
3
CH
3
CH
3
H
3
C
cis-1,3-dimetylxiclopentan

CH
3
CH
3
CH
3
H
3
C
trans-1,3-dimetylxyclopentan

(b) Etylxiclopantan. Khng c ng phn cis-trans.
C
2
H
5
C
2
H
5

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

C
2
H
5
H
CH
3
H
H
3
C C
2
H
5
cis-1-etyl-2-metylxiclobutan

H
C
2
H
5
CH
3
H
H
3
C C
2
H
5
trans-1-etyl-2-metylxiclobutan

Bi 13. Hai hp cht hu c A v B u c cng thc phn t C
5
H
10
. C hai u khng phn ng vi Cl
2

trong ti v lnh. A phn ng vi Cl
2
c nh sng, nhng cho mt sn phm duy nht l C
5
H
9
Cl. Cn hp
cht B cng tc dng vi Cl
2
trong cng iu kin nhng cho 6 ng phn C
5
H
9
Cl 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 C
5
H
10
nn chng c th l anken hoc xicloankan. Theo u bi, cc cht ny khng
tc dng vi Cl
2
ti v lnh nn A v B l cc xicloankan.
A tc dng vi Cl
2
cho mt monoclo duy nht nn A l xiclopentan
+ Cl
2
as
Cl + HCl

B tc dng vi Cl
2
(nh sng) tao ra 6 dn xut monoclo, nn B phi l metylxiclobutan.
Cl
2
-HCl
CH
3
CH
3
Cl
CH
3
Cl
CH
3
Cl
CH
3
Cl
CH
3
Cl
CH
2
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
109
0
28, 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 u. u c tnh theo cng thc
( )
(

= u
n
180 2 n
' 28 109
2
1
0


v d:
n 3 4 5 6 7 8 9
u
24
0
44 9
0
44 0
0
44 -5
0
44 9
0
33 12
0
46 -15
0
06
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 o v t bnh thng. Do s un cong nh vy, thc t gc lin kt ca vng ch bng 106
0

ch khng phi 109
0
28 v ln hn nhiu so vi gc cu to phng ca tam gic u (60
0
). Xiclopropan
rt d b m vng di tc dng ca hirohalogenua, Br
2
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 20-25
0
. 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 0
0
44, 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 C
s
. Cu dng na gh c trc i xng bc hai nn cn gi l cu dng C
2
.


Lu : Khi thc hin php quay phn t xung quanh trc i xng C
n
mt gc
n
2t
= sao cho phn t
trng vi chnh n. Trc quay C
n
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 ?
C
5

C
2


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 (C
1
-C
2
,
C
3
-C
4
, C
4
-C
5
v C
6
-C
1
) l phn b xen k, cn hai h thng cn li C
2
-C
3
v C
5
-C
6
) th phn b che khut.
Hn na nguyn t H C
1
v C
4
ch cch nhau 1,84
0
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 C
1
, C
3
v C
5
; mt phng th hai cha C
2
, C
4
v C
6
. 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 109
0
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 a-metylxiclohexan

Bi 21. Xt cu dng sau:
1
2
3
4
5
6

(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 CH
3
l lin kt trc (a)
CH
3
6

(b) C-1 km bn hn C-4, v lin kt trc km bn hn lin kt bin (e).
CH
3
1
H
3
C
4

(c) Nhm CH
3
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
3
C
H

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 C
5
H
12
). ng phn no bn
gii phng nng lng thp. Etylxiclopropan c sc cng gc ln v km bn hn metylxiclobutan.
CH
2
CH
3
CH
3
etylxiclopropan
metylxiclobutan
808,8 kcal/mol 801,2 kcal/mol

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

H
CH
3
H CH
3
H
H
3
C
cis-1,3,5-trimetylxiclohexan

H
CH
3
H
3
C H
H
H
3
C
trans-1,3,5-trimetylxiclohexan

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

H
CH
3
H
3
C H
H
H
3
C
CH
3
CH
3
H
CH
3
H
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 CH
3
(axial)
vo C-3 ca vng xiclohexan.
H
C(CH
3
)
3
H
CH
3
H
C(CH
3
)
3
trans-1-tert-butyl-3-metylxiclohexan

(b) Trc tin v xiclohexan dng gh vi mt nhm tert-butyl v tr equatorial. to ra cis-1-
tert-butyl-3-metylxiclohexan th phi gn nhm metyl vo C-3 v tr equatorial.
H
3
C
H
H
C(CH
3
)
3
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
C(CH
3
)
3
trans-1-tert-butyl-4-metylxiclohexan
H
3
C
H

(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
C(CH
3
)
3
cis-1-tert-butyl-4-metylxiclohexan
H
CH
3


Bi 26. V cc ng phn v gi tn ca hirocacbon c hai vng nhng khng cha nhm th ankyl c
cng thc phn t C
5
H
8
.
Bi gii
spiropentan 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
cng thc phn t C
6
H
10

Bi gii
spiro[2.3]hexan bixiclo[2,2,0]hexan
bixiclo[3,1,0]hexan
bixiclo[2,1,1]hexan xiclopropylxiclopropan

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 AH (kcal/mol) Xicloankan AH (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 (C
7
-C
11
) c tng hp vi hiu sut thp
hn so vi vng nh (C
3
-C
6
) hoc vng ln (C
12
-C
n
)?
Bi gii
(a) tnh nhit t chy ca mi nhm CH
2
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
CH
2
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
kcal/mol
Nhit t chy ca
CH
2
kcal/mol
Nhit t chy
khng c sc cng
gc kcal/mol
Sc cng gc
kcal/mol
3
499.83
166.61 472.24 27.59
4
655.86
163.97 629.65 26.21
5
793.52
158.7 787.07 6.45
6
944.48
157.41 944.48 0
7
1108.2
158.31 1101.89 6.31
8
1269.2
158.65 1259.31 9.89
9
1429.5
158.83 1416.72 12.78
10
1586
158.6 1574.13 11.87
11
1742.4
158.4 1731.55 10.85
12
1892.4
157.7 1888.96 3.44
13
2051.4
157.8 2046.37 5.03
14
2203.6
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 (C
7
-C
11
) 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
3
CH
3
H
H
H
3
C
(A)
H
H
H
3
C
CH
3
H
H
CH
3
(B)

Bi gii
Cu dng B bn hn cu dng A v c 2 CH
3
H 1,3-diaxial repulsions trong khi cu dng A c mt
CH
3
-CH
3
1,3-diaxial repulsion v hai CH
3
-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
CH
3
CH
3
(e)
(e)
CH
3
CH
3 (a)
(a) bn hn
trans-1,2-dimetylxiclohexan

CH
3
(e)
CH
3
(a)
cis-1,2-dimetylxiclohexan
CH
3
(a)
CH
3 (e)
Hai cu d ng ny c bn nh- nhau

Bi 32. V cc cu dng gh ca trans-1,3-dimetylxiclohexan v cis-1,3-dimetylxiclohexan. So snh
bn ca cc cu dng .
CH
3
(e)
CH
3
(a)
trans-1,3-dimetylxiclohexan
Hai cu d ng ny c bn nh- nhau
CH
3
(a)
H
3
C
(e)

CH
3
(e)
CH
3
(a)
cis-1,3-dimetylxiclohexan
H
3
C
(e)
CH
3
(a)
bn hn

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
CH
3
(e)
CH
3
(a)
trans-1,4-dimetylxiclohexan
bn hn
H
3
C
(e)
CH
3
(a)

CH
3
(e)
CH
3
(a)
cis-1,4-dimetylxiclohexan
CH
3
(a)
H
3
C
(e)
Hai cu d ng ny c bn nh- nhau.

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 1,2-
dimetylxiclododecan 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
CH
3
ONa.
Bi gii



Bi 37. Su hirocacbon A, B, C, D, E, F u c cng thc phn t C
4
H
8
. Cho tng cht vo brom trong
CCl
4
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 H
2
(Pd, t
0
) 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 C
4
H
8
:
CH
3
CH
3
Cl
CH
3
Cl
CH
3
CH
3
CH
3
Cl
CH
3
Cl
CH
3
I
I I I I I
CH
3
CH
3
1,3 - imetylxiclohexen
Khng t ch - c vH C
bn c nh khng ng phng
v u vtrcis i v i clo.
C 2 H C bn c nh
u t ch - c.
Chc 1 H l t ch - c.
1,3 - imetylxiclohexen
CH
3
CH
3
Cl
H
CH
3
H
H
3
C
Cl
H
CH
3
H
H
3
C
Cl
H
CH
3
CH
3

- V F hu nh khng phn ng vi Br
2
/CCl
4
, nn F l:

- E tc dng chm vi Br
2
/CCl
4
, 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 Br
2
/CCl
4
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).

A: CH
3
- CH
2
- CH = CH
2
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.





CH
3
CH
2
CH CH
2
CH
3
C CH
2
CH
3
CH
3
CH CH
CH
3
CH
3
CH CH
CH
3
H
2
C
H
2
C CH
2
CH
2
H
2
C CH
CH
2
CH
3
H
2
C
H
2
C CH
2
CH
2
H
2
C CH
CH
2
CH
3
CH
3
C CH
2
CH
3
B: CH
3
C C
CH
3
H
H
C: CH
3
C C
CH
3
H
H






TI LIU THAM KHO
[1.] ng nh Bch(2001), Nhng vn ha hc hu c, NXB Khoa hc v K thut
[2.] Trnh nh Chnh (1995), C s l thuyt ha lp th, Ti liu BDTX.
[3.] Trn Quc Sn, (1977), C s l thuyt ha hu c, NXB Gio dc.
[4.] Trn Quc Sn Trn Th Tu (2003), Danh php hp cht hu c.
[5.] Thi Don Tnh (2002) Gio trnh c s l thuyt ha hc, NXB Khoa hc v K thut.
[6.] 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