1.

Nm c bn cht, cu trc, bn ca
cc hp cht trung gian trong cc phn ng
hu c
MC TIU
2. Nu c cch phn loi tc nhn phn
ng v cc phn ng hu c
3. Trnh by c cc c ch phn ng
hu c c bn ( th, cng, tch)
1.S PHN CT LIN KT
1.1. Phn ct ng ly v phn ng gc
A
.
: B
.
A
.
+ B
.
cu trc hnh thp
bc x t ngoi, nhit cao, hay
peroxyd gc R
.

1.2. Phn ct d ly v cc phn ng ion
N E N E +
phn ng gc
C C
carbanion
carbocation
Cc tiu phn c in tch m tn cng vo vng ngho in
t ca phn t, tc nhn i nhn (nucleophile) Phn
ng i nhn
tiu phn c in tch dng tn cng vo vng c mt
in t ln tc nhn i in t (electrophile) phn ng
i in t
Phn ng d ly (phn ng ion) thng xy ra trong cc
dung dch ca cc dung mi phn cc v thng c xc
tc bi acid hoc base.
2. PHN LOI CC TC NHN PHN NG
2.1. Tc nhn i nhn (Nucleophile)
Nu ; Nu
Gm cc: anion, cc base Lewis (c mang cp in t
khng phn chia)
H

, H
2
N

, HO

, RO

, RS

, RCOO

, Hal

, HSO
3

,
NC

, RCC

ROH RNH
2
R
2
S , , RMgBr , RLi , LiAlH
4
- - -
2.2. Tc nhn i in t (Electrophile) E
+
Gm cc ion dng, cc acid Lewis
H
+
, H
3
O
+
, HNO
3
(NO
2
) , H
2
SO
4
(SO
3
) , HNO
2
(NO) , PhN
2
+ + +
BF
3
, AlCl
3
, ZnCl
2
, FeCl
3
C O R C Cl
O
R C
O
O C
O
R CO
2
, , ,
- - - -
2.3. Gc t do (Free radical)
Gm nguyn t hoc nhm nguyn t c cha in t c thn
Cl
-
, Br
-
, H
3
C
-
, HO
-
...
c kh nng phn ng cao
3. PHN LOI CC PHN NG HU C
Phn ng ng li:
A : B A
.
+ B
.

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 loi theo s phn ct lin kt
Phn ng d li : phn ng ion
A : B
A
-
+ B
+
- Carbocation cng bn khi cc nhm nguyn t nh
vo C(+) cng y e mnh
- Carbanion cng bn khi cc nhm nguyn t nh
vo C(-) cng ht e mnh
3.2. Phn loi theo kt qu phn ng
Phn ng th (S - Substitition)
1 nguyn t hay 1 nhm nguyn t c thay th
bng nguyn t hay nhm nguyn t khc
Phn ng cng ( A - Addition)
hai phn t kt hp vi nhau to thnh mt phn t mi
Phn ng tch loi (E - Elimination)
hai nguyn t hay nhm nguyn t b tch ra khi
mt phn t m khng c nguyn t hay nhm
nguyn t no thay th
Phn ng chuyn v
c s thay i v tr ca 1 hay nhm nguyn t trong
phn t
3.3 Phn loi theo giai on quyt nh tc phn ng
Phn ng n phn t (1):
Phn ng lng phn t ( 2 )
Phn ng a phn t ( n )
tun theo phng trnh tc bc 1
tun theo phng trnh tc bc 2
tun theo phng trnh tc bc n
3.4. Phn loi theo bn cht tc nhn phn ng
Phn ng gc (R): gc t do
Phn ng electrophin (E): tc nhn i in t (E
+
)
Phn ng nucleophin (N): tc nhn i nhn ( Nu
-
)
Bng phn loi cc phn ng hu c
Phn ng th
(S)
Phn ng cng hp
(A)
Phn ng tch loi
(E)
Th i
nhn
Th i
in
t
Th
gc
Cng i
nhn
Cng i
in t
Cng
gc
Tch n
phn t
Tch lng
phn t

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 (khi mo):

- Pht trin mch :
R
.
+ X : X R - X +
.
X
- Tt mch :
R
.
+
.
R R - R
X
.
+
.
X X - X
R
.
+
.
X R - X
di tc ng ca nh sng
4. C CH CA MT S PHN NG HU C
4.1. Phn ng th
X : X 2 X
.
R : H +
.
X R
.
+ HX
Ch
Kh nng phn ng th nguyn t H
cacbon bc 3 > bc 2 > bc 1
Sn phm l hn hp cht vi s nguyn t
halogen khc nhau tch bng ct phn on.
4.1.2.Th i in t S
E

- Xy ra nhn thm
- Halogen ha, nitro ha, sulfo ha tc nhn Br
+

H
E
+
+
E
H
+
+
H
E
+
Phc o
chm
nhanh
4.1.3. Phn ng th i nhn S
N

Tng qut
X = halogen (Cl, Br, I) , OH , OR ,
3
R N
+

Y
-
+ R X Y R + :X
=

Y l tc nhn i nhn: hal

, HO

, RO

CN , RCOO

- iu kin phn ng.
Ph thuc:
- Cu trc ca R trong RX
- Bn cht ca dung mi
- tc nhn i nhn mnh hay yu
Th i nhn n phn t S
N
1
(1)
(2)
Giai on chm quyt nh tc v = k [RX]
iu kin xy ra phn ng
- RX l bc ba
- phn ng tin hnh trong dung mi phn cc
- tc nhn Y
-
(Nu
-
) yu
R
1
- C - X
R
2
R
3
R
1
- C
R
2
R
3
+ : X
chm
R
1
- C
R
2
R
3
+ Y R
1
- C - Y
R
2
R
3
nhanh
Phn ng S
N
2 : Lng phn t
nhanh chm
v = k
2
[RX] [Y
-
] Giai on chm quyt nh tc
- gc R trong RX l bc mt (hoc bc hai)
iu kin xy ra phn ng
- Tc S
N
2 gim theo th t
R bc 1 > R bc 2 > R bc 3
RI > RBr > RCl > RF
Lu : Phn ng th S
N
thng i km phn ng tch loi E
Y R + :X
-
Y
-
+ R X [Y
o(-)
R X
o(-)
]
4.2. Phn ng cng hp
4.2.1. Phn ng cng A
E
Phn ng cng hp ca halogen vo alken
C
C
X
o+
X
o
+
- X
(-)
C
C
(+)
Br
Hay l
C
C
Br
+
+ X
(-)
C
C
Br
Br
chm
nhanh
Ch : - Dung mi phn ng khng phn cc: CCl
4

- X
2
= Cl
2
, Br
2
, Br Cl , I Cl, I - Br
Cng HX v cc HA khc nh HOH, H
2
SO
4
chm
nhanh
- Kh nng cng ca HX : HF << HCl < HBr < HI
- Carbocation trung gian cng bn th phn ng cng
cng d xy ra
- cng HA vo an ken khng i xng sn phm
l mt hn hp. Tun theo qui tc Maccopnhicop
- Cng dn xut ca anken c th ngc 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 cacbonyl ca andehyd, ceton
R
C = O
R'
o
-
o
+

+ Y - Z
o
-
o
+
chm
nhanh
Y
(+)

- Y
(+)
Y Z l H OH, H OR, H CN, H SO
3
Na , BrMg R
o
+
o
-
o
*
o
*
o
*

o
*
o
+

o
-
o
-
o
-
o
-
o
-

R
R'
O
(-)
Z
C
R
R' Z
OY
C
4.2.3.Cng hp gc A
R

- Khi cng hp HBr, HCl khi c mt peoxit vo anken
(khng xy ra vi HI v HF) Theo hiu ng Kharat (tri
vi quy tc Macconhicp)
R -O - O - R 2 RO
.

t
0

RO
.
+ HBr ROH + Br
.
(1) AH = - 23 kcal
hoc RO
.
+ HBr ROBr + H
.
(2) AH = + 39 kcal
(1) xy ra thun li hn (2)
- Giai on khi mo :
- Giai on pht trin mch
RCHCH
2
Br + HBr RCH
2
CH
2
Br + Br
.
.
- Giai on tt mch
Cc gc t do kt hp vi nhau to 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 to thnh sn phm, cho bit u l
sn phm chnh khi cho :
a. CH
3
- CH = CH
2
+ HCl
b. CF
3
- CH = CH
2
+ HCl
c. CH
2
= CH NO
2
+ HCl
d. CH
2
= CH Br + HCl
3. T tm hiu v phn ng cng hp ca ankadien v ankin


4.3. Phn ng tch loi
C C
H X
- HX
C C
X = Cl , Br , I , OCOCH
3
, OH
2
, SR
2
, NR
3
- Xy ra dn xut halogen, loi nc ca ancol
- Ph thuc vo cu to ca R trong RX v iu
kin phn ng
- Phn ng tch loi v phn ng th i nhn
lun cnh tranh nhau.
C ch tch E1 (n phn t)
Qua 2 giai on
- Giai on chm : b ion ho chm to ra carbocation
- Giai on nhanh: base mnh (ca KOH) tch mt
proton ca carbocation to thnh H
2
O v mt alken
chm
+ : X R
1
- C - X
R
2
CH
3
R
1
- C
R
2
CH
3
R
1
- C
R
2
CH
2
H
OH
+
nhanh
R
1
- C
R
2
CH
2
+ H
2
O
C ch tch E2 (lng phn t)
R - CH - CH
2
H X
+ Nu
-
[Nu
(-)
...H - C - C... X
(-)
]
R H
H H
Chm
nhanh
NuH
+ C = C + X
-
R
H
H H
Nu
-
= OH
-
, NH
2
-
(NaNH
2
)
Tc phn ng v = k [ RX ] [ Nu

]
Lu :
- Phn ng S
N
2 lun xy ra cng vi phn ng E2
- Nu Nu
-
tn cng vo C
o
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 ng ca Baz mnh
trong dung mi phn cc ( kim ru )
Bi tp vn dng
1. Gii thch c ch phn ng
CH
2
= C = CH
2
+ H
2
O ( H
+
)
2. Gii thch
CH
3
CCH + HBr CH
3
C(Br)=CH
2
CH
3
C(Br)
2
CH
3

3. Gii thch s to thnh sn phm v so snh kh nng
phn ng ca cc cht sau :
CF
3
CH = CH
2
+ HBr
Br CH = CH
2
+ HBr
CH
3
O CH = CH
2
+ HBr
4. Hy cho bit c bao nhiu sn phm c to thnh khi
cho izopren tc dng vi HBr
5. Khi cho hn hp gm 1,2 - dimetyl xyclopenten v
2,3 - dimetyl xyclopenten 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 metylaxetylen v cloaxetylen phn ng vi
HCl . Sn phm thu c cui cng u l cc hp
cht no. Cho bit c ch ca cc phn ng cng
thc cu to ca cc sn phm v rt ra nhn xt.
7. Hy gii thch ti sao :
CH
2
= CH - NO
2
+ HCl CH
2
(Cl) - CH
2
- NO
2
CH
2
= CH - Br + HCl CH
3
- CH(Br)Cl