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ORGANIC CHEMISTRY MECHANISM SUMMARY

FREE RADICAL SUBSTITUTION (FRS)


Exemplified by the substitution of methane by chlorine

Step 1: Intitiation
ClCl
uv Cl + Cl

Step 2: Propagation
a) Cl + CH4 CH3 + HCl
b) CH3 + Cl2 CH3Cl + Cl
Then (a), (b), (a), (b)

Step 3: Termination
a) Cl + Cl Cl2
b) CH3 + Cl CH3Cl
c) CH3 + CH3 CH3CH3

ELECTROPHILIC ADDITION
Exemplified by the addition of HBr to an alkene

H
C
Step 1

s lo w

Br

C
H

Step 2

H H

carbocation

Br

intermediate

C
+

:Br

fa s t

C C H
H Br

ELECTROPHILIC AROMATIC SUBSTITUTION


Exemplified by the addition of NO2 to benzene

Step 1
Generation
of
electrophile

HNO3 + 2H2SO4

NO2+ + H3O+ + 2HSO4-

H
Step 2
Electrophilic
attack

NO 2

s lo w

NO2
+

benzonium ion

Step 3
Loss of
proton

HSO 4

NO2

NO 2
fa s t

H2SO4

NUCLEOPHILIC SUBSTITUTION SN2 ONE STEP


R3

C X

Nu :
R1

R2

R3

Nu
R1

X
R2

pentavalent transition state

R3
Nu

C
R2

R1

NUCLEOPHILIC SUBSTITUTION SN1 TWO STEP


-

Nu :

R3
X

s lo w

R3

R3
fa s t

R1 R2

Nu

R1 R2

: Nu

R1 R2

R3
C

Nu

R 2 R1

carbocation intermediate
(planar)

two products
racemic mixture

NUCLEOPHILIC ADDITION
Exemplified by the addition of CN- to ethanal

Step 1
Generation
of
nucelophile

Step 2
Nucleophilic
attack

KCN

K+ + CN-

CN

H3C

:CN

s lo w

H3C

C
H

CN
H3C

H
Step 3
Protonation

CN
fa s t

H3C

OH

CN

H
Cyanohydrin