Escolar Documentos
Profissional Documentos
Cultura Documentos
ELECTROPHILIC ADDITION
Exemplified by the addition of HBr to an alkene
H H
H H
s lo w
Step 1
C C + H Br
H C
+
C + Br
-
H H H H
carbocation
intermediate
H H H H
-
Step 2 H C
+
C + :Br fa s t H C C H
H Br
H H
Step 2 s lo w
Electrophilic
NO2
+
+ +
attack
benzoniu
m ion
NO2
H NO2
Step 3
Loss of fa s t
proton HSO4
-
+ + + H2SO 4
R3
R3 R3
- -
Nu : C X Nu C X Nu C + X
R1 R1 R2 R1
R2 R2
pentavalent transition state
http://education.helixated.com
An Open Source Education Project
NUCLEOPHILIC SUBSTITUTION – S 1 – TWO STEP
N
-
R3 Nu : R3 R3 R3
s lo w fa s t
+
+
X C C Nu C C Nu
-
R1 R2 R1 R2 : Nu R 1 R2 R2 R1
carbocation intermediate two products
(planar) racemic mixture
NUCLEOPHILIC ADDITION
Exemplified by the addition of CN- to ethanal
Step 1
Generatio
n of KCN → K+ + CN-
nucleophi
le
CN
H3C
Step 2 -
- s lo w
Nucleophi
lic attack
C O + :CN H3C C O
H
H
CN CN
- fa s t -
Step 3
Protonati
H3C C O + H C N H3C C OH + CN
on
H H
Cyanohydrin
http://education.helixated.com
An Open Source Education Project