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Culture Documents
, H
2
N
, HO
, RO
, RS
, RCOO
, Hal
, HSO
3
,
NC
, RCC
# #
2.2. Tc nhn i din t (EIectrophiIe) E
+
Gm cc ion duong, cc acid L0is
+
,
+
,
, Ph
+ + +
BF
, All
, Znl
, F0l
# l
, , ,
2.3. Gc t do (Free radicaI)
Gm nguyn t hoc nhm nguyn t c cha din t dc thn
l
O
, Br
O
,
O
,
O
...
c kh nng phn ng cao
3. PHN LOAI CC PHN NG HU CO
Phn ng dng Ii:
A : B F A
.
+ B
.
l bn ca cc gc :
CH
3
.
< CH
3
CH
2
.
< (CH
3
)
2
CH
.
< (CH
3
)
3
C
.
CH
3
CH
2
CH
2
.
< CH
2
= CH CH
2
.
< C
6
H
5
CH
2
.
V d:
X
.
: X
.
2X
.
RO
.
: RO
.
2RO
.
phn ng gc
3.1. Phn Ioai theo s phn ct Iin kt
Phn ng d[ Ii : phn ng ion
)
Bng phn Ioai cc phn ng hu co
Phan ng th
(S)
Phan ng cng hp
(A)
Phan ng tch loi
(E)
Th i
nhn
Th i
din
tu
Th
gc
Cng i
nhn
Cng i
din tu
Cng
gc
Tch don
phn tu
Tch lung
phn tu
S
N
1, S
N
2 S
E
S
R
A
N
A
E
A
R
E1 E2
4.1.1 Phn ng th gc S
R
vo carbon no
Kch thch (khoi mo):
Pht trin mach :
R
.
+ X : X F R X +
.
X
Tt mach :
R
.
+
.
R F R R
X
.
+
.
X F X X
R
.
+
.
X F R X
dui tc dng ca nh sng
4. CO CH CA MQT S PHN NG HU CO
4.1. Phn ng th
X : X F 2 X
.
R : H +
.
X F R
.
+ HX
Ch
Kh nng phn ng th nguyn t H
cacbon bc 3 > bc 2 > bc 1
Sn phm I hn hp cht vi s nguyn t
haIogen khc nhau tch bng ct phn doan.
4.1.2.Th i din t S
E
Xy ra nhn thom
HaIogen ha, nitro ha, suIfo ha . tc nhn Br
+
H
E
+
+
E
H
+
+
H
E
+
Phc 9
chm
nhanh
4.1.3. Phn ng th i nhn S
N
Tng qut
= halog0n l, Br, , , # ,
+ R - X F - R + :X
=
l tc nhn i nhn: hal
, #
,
, #
(Nu
) yu
R
1
C X
R
2
R
3
R
1
C
R
2
R
3
+ :
chm
R
1
C
R
2
R
3
+ R
1
C
R
2
R
3
nhanh
Phn ng S
N
2 : Lung phn t
nhanh chm
v = k
2
[RX] [
+ R - X [
0()
. R . X
0()
]
4.2. Phn ng cng hp
4.2.1. Phn ng cng A
E
!hn ng cng ho5 ca halogen vo alken
C
C
X
0
X
0
+
- X
(-)
C
C
(+)
Br
Hay I
C
C
Br
+
+ X
(-) C
C
Br
Br
chm
nhanh
Ch : ung mi phn ng khng phn cc: CCI
4
X
2
= CI
2
, Br
2
, Br - CI , I - CI, I Br
ng HX v cc HA khc nh HOH, H
2
SO
4
chm
nhanh
Kh nng cng ca HX : HF << HCI < HBr < HI
Carbocation trung gian cng bn th phn ng cng
cng d xy ra
cng HA vo an ken khng di xng sn phm
I mt hn hp. Tun theo qui tc Maccopnhicop
Cng dn xut ca anken c th nguc vi qui
tc Maccopnhicop
C
C
+ H - A
- A
(-)
C
C
(+)
H + A
(-)
C
C
H
A
4.2.2. Phn ng cng A
N
Phn ng ca nhm cacbonyI ca andehyd, ceton
R
C O
R'
0
0
+
+ Y - Z
0
0
+
chm
nhanh
(+)
(+)
- Z I H - OH, H - OR, H - CN, H - SO
3
Na , BrMg - R .
0
+
0
0
+
0
R
R'
O
(-)
Z
C
R
R' Z
OY
C
4.2.3.ng hp gc A
R
Khi cng hp HBr, HCI khi c mt peoxit vo anken
(khng xy ra vi HI v HF) F Theo hiu ng Kharat (tri
vi quy tc Macconhicp)
R O O R F 2 RO
.
t
0
RO
.
+ HBr F ROH + Br
.
(1) H = 23 kcaI
hoc RO
.
+ HBr F ROBr + H
.
(2) H = + 39 kcaI
(1) xy ra thun Ii hon (2)
Giai doan khoi mo :
Giai doan pht trin mach
RCHCH
2
Br + HBr F RCH
2
CH
2
Br + Br
.
.
Giai doan tt mach
Cc gc t do kt hp vi nhau tao thnh phn t
R - CH CH
2
+ Br
.
R - CH -
.
CH
2
Br
(I)
R -
.
CH - CH
2
Br(II)
Bi tp vn dng
1. Xt kh nng phn ng vi HX ca cc cht sau :
a. CH
2
= CH
2,
, CH
3
CH = CH
2
, (CH
3
)
2
C = CH
2
,
(CH
3
)
2
C = CH CH
3
b. CH
2
= CH
2,
, CH
2
= CHBr , CH
2
= CH COOH
2. Gii thch s tao thnh sn phm, cho bit du I
sn phm chnh khi cho :
a. CH
3
CH = CH
2
+ HCI F
b. CF
3
CH = CH
2
+ HCI F
c. CH
2
= CH - NO
2
+ HCI F
d. CH
2
= CH - Br + HCI F
3. T tm hiu v phn ng cng hp ca ankadien v ankin
4.3. Phn ng tch Ioai
= l , Br , ,
, $#
, #
v mt alk0n
chm
+ : R
1
C X
R
2
CH
3
R
1
C
R
2
CH
3
R
1
C
R
2
CH
2
H
+
nhanh
R
1
C
R
2
CH
2
+ H
2
O
o ch tch E2 (lng phn t)
R CH CH
2
H X
+ Nu
[Nu
()
...H C C... X
()
]
R H
H H
hm
nhanh
NuH
+ C C + X
-
R
H
H H
Nu
= OH
, NH
2
(NaNH
2
)
Tc d phn ng v = k [ RX ] [ Nu
]
Luu :
Phn ng S
N
2 Iun xy ra cng vi phn ng E2
Nu Nu
tn cng vo C
-
th xy ra phn ng S
N
2
Nu Nu tn cng vo H
.
th xy ra phn ng E2
Phn ng E2 cn c tc dng ca Bazo manh
trong dung mi phn cc ( kim ruu )
Bi tp vn dng Bi tp vn dng
1. Gii thch co ch phn ng
CH
2
= C = CH
2
+ H
2
O ( H
+
) F
2. Gii thch
CH
3
-CCH + HBrF CH
3
C(Br)=CH
2
F CH
3
C(Br)
2
CH
3
3. Gii thch s tao thnh sn phm v so snh kh nng
phn ng ca cc cht sau :
CF
3
- CH = CH
2
+ HBr F
Br - CH = CH
2
+ HBr F
CH
3
O - CH = CH
2
+ HBr F
4. Hy cho bit c bao nhiu sn phm duc tao thnh khi
cho izopren tc dng vi HBr
5. Khi cho hn hp gm 1,2 dimetyI xycIopenten v
2,3 dimetyI xycIopenten phn ng vi HBr khng c
peroxit cho 2 sn phm, cn khi cho hn hp trn
phn ng vi HBr c mt peroxit cho 6 sn phm.
Hy cho bit cu trc ca cc sn phm trong cc
phn ng trn
6. Cho metyIaxetyIen v cIoaxetyIen phn ng vi
HCI . Sn phm thu duc cui cng du I cc hp
cht no. Cho bit co ch ca cc phn ng cng
thc cu tao ca cc sn phm v rt ra nhn xt.
7. Hy gii thch tai sao :
CH
2
= CH NO
2
+ HCI F CH
2
(CI) CH
2
NO
2
CH
2
= CH Br + HCI F CH
3
CH(Br)CI