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Chapter 16:Substituent Effects in Aromatic Substitution

Chapter 16 Overview:
Bromination
Br2, FeBr3

Iodination
I2, CuCl2

Br

Chlorination
Cl2, FeCl3

Nitration

Friedel-Crafts Alkylation
RCl, AlCl3

SO3H

Friedel-Crafts Acylation
AlCl3

Nitro Reduction to an Amine


NO2

SnCl2, H3O

OH

NaOH

NH2

OH

Alkali Fusion of Aromatic Sulfonates


SO3H

R group may rearrange


Substrate must be at least as reactive as a halobenzene
Deactivated rings don't react

O
Cl

NO2

HNO3, H2SO4

Sulfonation
SO3, H2SO4

Cl

Benzyne Intermediate for Amination

H3O

Br

NH2

NH2

NH3

Addition/Elimination to an Activated Aryl Halide


OH

Br
O2N

NO2

OH
H3O

O2N

NO2

CH3

Benzylic Bromination of Alkylbenzenes with NBS


CH3

NBS

CH2Br

CCl4
Clemeson Reduction of Dialkyl Ketones
O

Zn(Hg)/HCl

Oxidation of Alkylbenzene Side Chains


KMnO4

COOH

H2O
reaction doesn't work with tertriary alkanes
Reduction of Aryl Alkyl Ketones
O
C

CH3

H2, Pd

only works with benzylic ketones


Catalytic Hydrogenation
H2/Rh/C

H2
C

CH3