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L xem xt cc phn ng di ba gc :
Cc giai on ca phn ng
Bn cht ca s t v thnh lp cc ni c trng ca
phn ng
Trng thi chuyn tip ca phn ng
Gii thch sn phm sinh ra ph hp vi qu trnh thc
nghim.
PHN NG HU C
C IM
-Din ra vi tc chm
-Cc phn ng thng thun nghch, hiu sut phn ng
khng cao.
-Cc phn ng thng xy ra theo nhiu hng khc nhau
to thnh hn hp sn phm.
dng nhit, xc tc v k thut thc hin phn ng
PHN LOI
1. Phn ng th (Substituation)
CH3-H + Cl2
CH3-Cl + HCl
2. Phn ng cng
CH2=CH2 + Cl-Cl Cl-CH2CH2-Cl
3. Phn ng tch loi
H-CH2-CH2-OH CH2=CH2 + H2O
C6H5
CH CH CH2
C6H5
CH CH CH2
OH
OH
R'
C N OH
R
R C N R'
O H
hv
Cl
Cl
CH3
CH3
Br
CH3
CH3
C6H4NO2p
pO2NC6H4
C6H4NO2p
Br
C
CH3
OH
C6H4NO2p
pO2NC6H4
C
C6H4NO2p
d
Cl
d
< CH3
OC2H5
Cl
CH3 O C2H5
NO2
NO2
CH4
Cl
CH3
HCl
CH3
Cl2
CH3
Cl
I. Phn ng th
1.Phn ng th gc t do:
Gm ba giai on
2504000c
X2
2X.
Hoc nh sng t ngoi (h)
2X. + RH
HX
+ R.
R.
+ X2
RX
+ X.
X.
+ X.
X2
R.
+ R.
RR
X.
+
R.
RX
: Giai an khi mo
: Giai an truyn i
: Giai an kt thc
C Y
Nu
Nu C
Cht nn
Sn phm
Cht thn hch
Trng thi chuyn tip
Nhm xut.
(nghch chuyn
cu hnh)
H
H
H
HO
C Br
H
Br
HO
H
HO
H
H
Br
Vd:
+ HX
SN1
CH3
CH3
CH3 C OH
CH3
H Br
C Nu
Nu C
Hn hp tiu trin
CH3
CH3 C OH
Nu
CH3
CH3 C X
H2O
CH3
CH3
CH3 C OH2
CH3
- H2O
CH3
CH3 C
CH3
Br
CH3
CH3 C Br
CH3
SN1
Cht nn
Khng nh hng
Nhm xut
Cn nhm xut tt ( Cc
anion bn, baz yu).
Cn nhm xut tt ( cc
anion bn, baz yu ).
Dung mi
Cht xc tc
H
E
H
E
E
A
HA
Phn ng th thn in t
Cl2
Vai tr ca Fe:
Fe
Cl
Fe
0
30 c
+
Cl2
FeCl3
Cl
Cl
Cl
Fe Cl
Cl
HCl
Cl
Cl
Cl
Fe Cl
Cl
Cl
FeCl4
C C
KOH/C2H5OH
CH3CH CHCH3
Br
Br
H
CH3
Br
CH3CH2O
CH3
H
C C
H
CH3
Br
CH3
H
H
C C
CH3
2. Phn ng kh E1
L phn ng bc mt, trng thi trung gian qua ion cacbonium. Vn tc
phn ng ch ty thuc vo nng cht nn.
CH3
CH3
H
Etanol
CH3 C
Br + C2H5ONa
C C
0
25
CH3
H
c
CH3
C ch:
CH3
CH3
C
CH3
Br
-Br
CH3
CH3
H
C C H
H
C 2 H5 O
CH3
CH3
C C
H
H
CH3
CH3
SN2(21%)
E2(79%)
*Phn ng E1 bao gi cng km theo SN1
CH3
CH3
C
CH3
Br
H2O, Etanol
650 c
CH3
CH3
C
CH3
OH
SN1(64%)
CH3
CH3
C C
H
H
E1(36%)
CH3
Ch
Thng khng c s gii hn r rng gia E1, SN1, E2,
SN2.
+ Dung mi phn cc v ion cacbonium bn thng u
tin E1 v SN1.
Dung mi t phn cc v ion cacbonium t bn thng
u tin E2 v SN2.
+ Tc nhn tnh thn hch mnh, baz yu thng cho
phn ng th.
Tc nhn thn hch yu, tnh baz mnh thng cho
phn ng kh.
III.Phn ng cng
1. Cng thn in t vo ni i C = C
Phn ng xy ra theo hai giai on:
+ Giai on I (chm): To onium vng hoc hp cht trung
gian l ion carbonium.
+ Giai on II (nhanh): cht thn hch tc kch vo cht
trung gian
a/. Cng HA vo ni C=C
C
C
H A
I
C
A
II
C H
C A
C H
A C
CH3
CH3
CH3
C CH2
C CH2
HBr
CH3
C Br
CH3
CH3
CH3
H
C CH2
Br
CH3
CH3
C Br
CH3
Br Br
H - Br
Br
C
Br
Br
CH3
H
CH3 a
C
b
H
CH3
a
Br
H
CH3
(2R, 3R)2,3dibromobutan
(2S,3S)2,3dibromobutan
H
CH3
Br
b
H
CH3
Br
Br
C
H
CH3
Lu :
S hin din ca trung gian onium vng hay carbonium
c xc nhn khi mi trng phn ng c s hin din
ca cc ion X-, NO3-, H2O ta s c sn phm tng
ng.
X
CH2=CH2
Br2
Br
CH2
CH2
Hay CH2Br
CH2
NO3
H2 O
CH2Br
CH2Br
CH2Br
CH2ONO2
CH2Br
CH
OH2
X : Br, Cl, I
CH2Br
CH
OH
Nu
Nu
C
O
+ Nu xc tc l acid:
C
C
O
Nu
Nu
O
+ Nu xc tc l baz:
Nu
C
OH
OH
Nu
C
O
H B
Nu
C
OH
Cc v d
- Cng alcol
R C R'
R"
OH
R'
- Phn ng ester ha
R C O H
R C O H
R C O
O
H O R'
R'
R'
R C
O H
OH
O H
R C O H
O H
R'
OR"
H2O
R'
O H
R C O H
O H
O H
OH
R CH C H
O
R
RCH2CHCHCHO
OH
HO H
OH
R CH C H Hay R CH C H
O
O
R
RCH2 C H
RCH2CHCHCHO
O