BI TP C CH PHN NG

Bi tp s 1: Cho s :
CH3 CH3
CH
Cl2, Fe , askt NaOH
B Cl2 C NaOH
D E
t0, p
Cumen(A)
Cc chui phn ng u din ra theo t l mol 1:1, cc cht ghi trn s
u l sn phm chnh. Vit cc phng trnh phn ng v cho bit
c ch cc phn ng t A B, B C. Gii thch s to thnh sn phm
chnh ca 2 phn ng ny.
HCl
Hexin-3 C6H12Cl2
Bi tp s 2: a. Cho s sau : xt , t0

Vit c ch phn ng v cu trc ca sn phm to thnh.

Br2 , 1:1
b. Butin-2 A
Xc nh cu trc ca A v gi tn.
Bi tp s 3: 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 tp s 4: Hon thnh cc chui phn ng sau:
a. CH3I + (CH3)2CHO-
b. CH3O- + (CH3)2CHI
c. (CH3)3CCH2I + C2H5O-
d. (CH3)3Br + CH3O-
Cl
e. + (CH3)3CO-
CH2Br

f. + (CH3)2CHCH2O-
CH2O-

g. + (CH3)2CHCH2Br
Bi tp s 5: Hon thnh cc phn ng sau:
CH3
H2O
CH3 C CH2Br
SN1, E1
a. CH3

CH3
H2O
CH3 CH2 C CH2 CH3
SN1, E1
b. Br
CH3
H2O
CH3 C CH CH3
SN1, E1
c. CH3 Cl

CH2
H2O
CH2 CH CH2Br
SN1, E1
d. CH2

Bi tp s 6: Hy cho bit sn phm to thnh khi thc hin phn ng

hirat ho cc cht sau vi xc tc axit H+. Trnh by c ch phn ng.
a. propan-1,2-iol.
b. 2-metylpropan-1,2-iol.
c. 2-metylbutan-2,3-iol.
Bi tp s 7:
a. Vit phng trnh phn ng khi cho alyl clorua, benzyl clorua tc dng
vi dung dch KOH un nng.
b. Hp cht hu c X c cu to khng vng c cng thc C 4H7Cl v c cu
hnh E. Cho X tc dng vi dung dch NaOH trong iu kin un nng
thu c hn hp sn phm bn c cng thc C4H8O.
Hy cho bit cu trc ca X v cu hnh ca sn phm to thnh.
Bi s 8 : Vit cc phng trnh phn ng theo t l s mol 1:1 ca cc
cht sau y vi dung dch Br 2 trong CCl4. Gii thch s nh hng phn
ng :
a, CH2= CH- CH2- C CH b, CH2= CH- C CH
c, (CH3)2C= CH- CH2- CH= CH2 d, CH3- CH= CH- CH2- CH= CHBr
Bi s 9 : Khi cho iso-butilen vo dung dch HCl c ha tan NaCl, CH 3OH c
th to ra nhng hp cht g ? Gii thch.
Bi s10 : Vit sn phm v gii thch c ch phn ng ca etilen vi :
a, Br2 trong CCl4 b, Br2 trong H2O c, Br2 trong nc c pha
NaCl

Bi gii mu
Bi tp s 1:
CH3 CH3 CH3 CH3

CH CH
Fe, t 0
+ Cl2 + H Cl
(B)
Cl
CH3 CH3 CH3 CH3

CH C Cl
askt + HCl
+ Cl2
(C)
Cl Cl

CH3 CH3 CH3 CH3

C Cl C OH

+ NaOH + NaCl
(D)

:Cl Cl

Nguyn t Cl lin kt trc tip vi vng benzen kh b thu phn do c s

gii to electron ca Cl vo vng benzen nh hiu ng +C.
CH3 CH3 CH3 CH3

C OH C OH
0
t ,p
+ NaOH + NaCl
(D)

:Cl OH
 C ch phn ng t A B
Phn ng theo c ch electrophin vo nhn thm SEAR.
t0
3 Cl2 + 2 Fe 2 FeCl
_3
+
FeCl3 + Cl2 Cl ... FeCl4
CH3 CH3
CH3 CH3
CH
CH
_
+
+ Cl ... FeCl4 + + FeCl4

H Cl
Phc

CH3 CH3 CH3 CH3

CH CH

+ + H

H Cl
Cl
Phc

H + FeCl4 FeCl3 + HCl

Do gc (CH3)2CH- c hiu ng +I l nhm th loi I nn nh hng

phn ng th tip theo vo v tr ortho v para. Nn giai on to
phc c th c hai phc sau :
CH3 CH3 CH3 CH3
CH CH
Cl
(II)
+ (I) + H
H Cl

Do gc (CH3)2CH- c s n ng v khng gian nn dn n Cl + kh tn

cng vo v tr ortho nn phn nc (II) kh hnh thnh hn. Cho sn
phm chnh l :
 CH3 CH3
CH

Cl

C ch phn ng B C
Phn ng th theo c ch gc SR, gm cc giai on :
- Khi mo phn ng :
as .
Cl2 2 Cl
- Pht trin mch :
CH3 CH3 CH3 CH3
.
CH C
.
+ Cl + HCl

Cl Cl
CH3 CH3 CH3 CH3
. C
C Cl
.
+ Cl2 + Cl

Cl Cl

C nh vy
- Ngt mch
. .
Cl + Cl Cl2
. .
R + Cl R Cl
. .
R + R R R
CH3
.
V i gc t do R : Cl C.
CH3
Trong giai on pht trin mch c th sinh ra cc gc sau :
 .
CH3 CH3 CH3 CH2
. CH
C

(I) (II)

Cl Cl

Gc (I) bn hn do c hiu ng +C ca vng benzen v hiu ng +H. Gc

(II) km bn hn do ch c hiu ng +H.
Nn sn phm chnh l :
CH3 CH3
C Cl

Cl

Bi tp s 2:
Cl

CH3 CH2 C C CH2 CH3 + 2 HCl CH3CH2 CH2 C CH2CH3

. Cl

C ch :

CH3 CH2 C C CH2 CH3 HCl CH3 CH2 C C CH2 CH3

Cl CH2 C C CH2 CH3

CH3

H Cl
H
HCl
CH3 CH2 C C CH2 CH3

H Cl

H Cl
Cl CH3 CH2 C C CH2 CH3

H Cl

b.Phn ng tun theo quy tc Maccopnhicop v theo hng cng hp trans.

 Br
1:1
2 CH3 C C CH3 + Br2 CH3 C C CH3
cng trans
Br
trans - (hay E-)2,3 -
ibrom-2-buten
Br Br
Br Br
CH3 C C CH3 CH3 C C CH3 Br CH3 C C CH3

Br

Bi tp s 3:
CH3
Cl

CH3

CH3 CH3 CH3

Cl Cl
CH3 CH3

Cl
CH3
(I) (II)
(III)

H H
H
H H H3C

CH3 CH3
CH3
H3C Cl H
H3C
Cl Cl
C 2 H C Khng tch c vH Chc 1 H l tch c
bn cnh u C bn cnh khng ng
tch ra ph ng v
u vtrcis
i
v i clo
CH3
CH3

1,3-
imetylxiclohexen

CH3
CH3
1,3-imetylxiclohexen

Quy tc Barton Hassel : Phn ng tch nucleofin vng no ch chy

tt khi cc nhm th c tch ra v tr axial trans.
Bi tp s 4:
CH3

a. CH3I + (CH3)2CHO- I- + CH3 CH OCH3

b. CH3O- + (CH3)2CHI CH3OH + I- + CH2 CH CH3
c.
 CH3

CH3 C CH2 OC2H5 + I -

CH3
CH3 (Ph)

CH3 C CH2I + C2H5O-

CH3 CH2
CH3 C + C2H5OH + I
-

CH3 CH2
Kh vvng ny nh km bn

d. (CH3)3CBr + CH3O- CH2 = C (CH3)2 + CH3OH + Br-

e.
Cl
+ (CH3)3CO- + (CH3)3COH + Cl-
f.
CH2Br CH2OCH2CH(CH3)2

+ (CH3)2CHCH2O- + Br-
g. CH2CH2CH(CH3)2
+ Br-
CH2O-
+ (CH3)2CHCH2Br
CH2OH
CH2 C CH3 + Br-
+
CH3

Bi tp s 5:
a.
CH3 CH3
H2O
CH3 C CH2Br CH3 C CH2 CH3 C CH2 CH3
SN1, E1
CH3 CH3 CH3
OH

CH3 C CH2 CH3

CH3 C CH2 CH3 CH3

CH3 CH3 C CH CH3 + CH2 C CH2 CH3

CH3 CH3
 CH3

CH3CH2 C CH2 CH3

CH3 OH
H2O
2 CH3 CH2 C CH2 CH3 CH3 CH C CH2 CH3
SN1, E1
Br CH3

CH3 CH2 C CH2

b. CH2 CH3

c
CH3 CH3
H2O
3 CH3 C CH CH3 CH3 C CH CH3
SN1, E1
CH3 Cl CH3
CH3 C C CH3
CH3
Chuyn v
CH3 CH3 CH3
CH3 C CH CH3
sn phm OH CH3
chnh
CH3 CH3 C CH3
C

CH3

d.
CH2 CH2
H2O
CH2 CH CH2Br CH2 CH CH2
SN1, E1 CH2 OH
CH2 CH2
CH2 C CH3
CH2
CH2 H CH2 CH2
Chuyn v
CH2 C CH2 CH2 C CH3 CH2 C CH2
hirua
CH2 CH2 CH2
OH CH

CH2 CH2 C CH3

M vng CH2
CH2 CH CH3
CH2

Bi tp s 6:
a)

CH3 CH CH2 H CH3 CH2 CHO + H2O

OH OH
 CH3 CH CH2 H CH3 CH CH3 CH CH2
.CH2
-H2O
OH OH OH OH2 OH
Chuyn v
CH3 -H CH3
CH CH2 CH3 OHC CH2

OH
CH3 CH H CH3 CH
CH2 .CH2 CH3 CH CH2
-H2O
C ch : OH OH OH2 OH OH

Chuyn v
hirua
CH3 CH2 CH H CH3CH2 CHO
OH
CH3 CH3
H
b.CH3 C CH2 CH3 CH CHO + CH3 C CH2CH3
-H2O
OH OH O
(cchtr
nh by t ng t c
u a.)
CH3 CH3
H
c. CH3 C CH CH3 CH3 C CH CH3 +CH3 C CHO
-H2O
OH OH O CH3 CH3
(cchtr
nh by t ng t c
u a.)

Cn lu : Trong trng hp mt nguyn t cacbon COH c hai

nhm th khc nhau th nhm no c tnh cht y electron mnh
hn s b chuyn dch.
Bi tp s 7:
a. CH2 CH CH2Cl + KOH CH2 CH CH2OH + KCl
CH2Cl CH2OH

+ KOH + KCl

b. Vi cu hnh E, C4H7Cl c 3 cu trc sau :

CH3 CH3 C2H5 H CH3 H
C C C C C C
.. ..
H Cl H Cl H CH2Cl

I II III

C4H7Cl C4H8O : C4H7OH

t0

I v II rt kh thu phn do s lin hp gia cp electron khng lin kt

ca Cl v ni i. Tho mn iu kin trn l III.
CH3 H (-) CH3 H
- Cl chuyn v
C C C C CH3 CH CH CH2

H CH2Cl H CH2
(-)
(-) OH
OH
*
CH3 CH CH CH2
CH3 H
C C OH

H CH2OH (Bin thra xemic)

(Dng E)

Bi tp s 8
a, CH2= CH- CH2- C CH + Br2 CH2Br- CHBr- C CH
2
Kh nng phn ng cng electrophin ca lin kt i (C sp ) cao hn lin
2
kt ba (Csp) do m in Csp > Csp nn kh nng gi eletron ca Csp
bn hn.
1,4
CH2Br-CH=C = CHBr

1 2 3 4 +Br2 3,4
CH2 = CH - C = CH CH2=CH-CBr = CHBr

1,2
CH2Br-CHBr-C = CH
b,
C 3 sn phm cng : cng 1,4 ; cng1,2 ; cng 3,4 do c s lin hp
gia cc lin kt p ca lin kt i v lin kt ba.
6 5 4 3 2 1
c, (CH3)2C = CH - CH2- CH = CH2 + Br2 (CH3)2CBr- CHBr - CH2 -CH = CH2
Do C5 c hai nhm CH3 y electron v pha lin kt i nn mt
electron lin kt C5 = C4 cao hn lin kt C2 = C1 nn kh nng phn ng
electrophin ca C5 = C4
6 5 4 3 2 1
d, CH3-CH = CH - CH2 -CH = CHBr + Br2 CH3CHBr - CHBr - CH2 - CH = CH2

Kh nng cng AE ca lin kt C5 = C4 cao hn lin kt C2 = C1 do C5 = C4

c
nhm CH3 y electron lm tng mt electron, cn C2 = C1 c Br ht
electron
lm gim mt electron.
Bi tp s 9
Sn phm phn ng l hn hp gm :
CH3
CH3 - CBr - CH3 ; CH3 - C - CH3
CH3 OH
CH3
CH3 - CCl - CH3 v CH3 - C- O-CH3
OH CH3

Gii thch da vo c ch phn ng

-Trong dung dch c cc qu trnh phn li :
HBr H+ + Br- NaCl Na+ + Cl-
-Do trong dung dch c 4 tc nhn l Br-, Cl-, H2O v CH3OH c
kh nng kt hp vi cacbocation. Phn ng theo c ch cng
electrophin (AE).
-Trc ht tc nhn electrophin(H +) tn cng vo C- to
cacbocation (giai on chm) :
+ - + chm +
CH3 C CH2 + H CH3 - C - CH3
CH3
CH3

-Sau l qu trnh kt hp cacbocation vi cc tc nhn Br -, Cl-,

H2O v CH3OH to thnh sn phm (giai on nhanh) :
 CH3 CH3
CH3 - C (+) + Br- nhanh
CH3 - C - Br
OH CH3

CH3
CH3
CH3 - C (+) + Cl- nhanh
CH3 - C - Cl
OH
CH3

CH3
CH3
CH3 - C (+) + HOH nhanh
CH3 - C - OH + H+
OH CH3

CH3 CH3
CH3 - C (+) + CH3OH nhanh CH - C - O - CH
3 3 + H+
OH CH3

Bi tp s 10
H H H Br
C =C CCl4
+ Br2(dd) H-C-C-H
H H
a Br H

C ch :
Giai on chm (quyt nh tc phn ng) to ra

- -
CH2 = CH2 + Br Br CH2 - CH2 - Br
cacbocation.
Giai on nhanh :
Br

CH2 - CH2 - Br + Br- CH2 - CH2
Br

b, Trong dung mi nc c sn phm Br-CH2-CH2-OH (etilenbromhirin) theo c ch

phn ng : Br2 + H2O HBr + HOBr {H+, Br-, HOBr}

Br Br
+ - +
CH2=CH2 + Br - OH CH2-CH2 + OH - CH2-CH2
OH
 Br
+ Br
CH2-CH2 + Br - CH2 - CH2
Ngoi ra c th c : Br

c, Tng t nh b, nhng cn c :
Br Br
+
CH2-CH2 + Cl- CH2-CH2
Cl

Khng to ra 1,2 - icloetan do khng c tc nhn Cl +

Nh vy : Mun cho phn ng ch to ra BrCH2-CH2Br phi tin hnh phn ng trong
dung mi tr ( v d : CCl4)