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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
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 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
C Cl C OH
+ NaOH + NaCl
(D)
:Cl Cl
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
+ + H
H Cl
Cl
Phc
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
Cl
Bi tp s 2:
Cl
. Cl
C ch :
H Cl
H
HCl
CH3 CH2 C C CH2 CH3
H Cl
H Cl
Cl CH3 CH2 C C CH2 CH3
H Cl
Br
Bi tp s 3:
CH3
Cl
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
CH3 CH2
Kh vvng ny nh km bn
+ (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 CH3
CH3
CH3 OH
H2O
2 CH3 CH2 C CH2 CH3 CH3 CH C CH2 CH3
SN1, E1
Br CH3
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
Bi tp s 6:
a)
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.)
+ KOH + KCl
I II III
H CH2Cl H CH2
(-)
(-) OH
OH
*
CH3 CH CH CH2
CH3 H
C C OH
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
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
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