Aromatic Organic Synthesis Routes

NH2

Phenylamine Sn Conc HCl Reduction Reflux NO2

Nitrobenzene Conc. H2SO4 HNO Electrophilic 3 Substitution >55 C. Electrophilic COR Friedal-Crafts Cl Acylation Substitution RCOCl (RCO)2O Cl2 AlCl3 AlCl3 Reflux r.t.p, anhydrous Phenyl Ketone Chlorobenzene Benzene CH3Cl AlCl3 Friedal-Crafts Alkylation CH3

methylbenzene

Reactions of Benzene.
1. Benzene C6H6 Reagent: Conditions: Type: Mechanism: Chlorobenzene C6H5Cl Cl2 (g), AlCl3, Anhydrous r.t.p. Electrophilic Substitution Required.
Cl Cl Al Cl Cl

A2 P77

Cl2

Cl

Al Cl

Cl

Cl

H Cl
+

Cl

Cl

2.

Benzene

Phenyl Ketone 3

A2 P77

C6H6 Reagent: Conditions: Type: Mechanism:

Cl Cl Al Cl

C6H5COR RCOCl, AlCl3 Anhydrous HUR Friedal-Crafts Acylation Required.

O Cl Cl R Al Cl Cl O

+
Cl

+C R

H COR+ + COR

COR

3.

Benzene C6H6

Methyl benzene C6H5CH3

A2 P77

Reagent: Conditions: Type: Mechanism:

Cl Cl Al Cl

CH3Cl, AlCl3 Anhydrous HUR Friedal-Crafts Alkylation Required.

Cl

CH3

Cl

Cl

Al Cl

Cl

CH3+

H CH3
+

CH3

CH3

4.

Benzene C6H6 Reagent:

Nitrobenzene C6H5NO2 Conc. HNO3 / H2SO4

A2 P78

Conditions: Type: Mechanism:

< 55oC Electrophilic substitution Required. [H2NO3]+ + HSO4NO2+ + H2O

H2SO4 + HNO3 Then [H2NO3]+

NO2+

NO2

NO2

Reaction of Nitrobenzene
5. Nitrobenzene C6H5NO2 Phenylaminie C6H5NH2 A2 P78

Reagent: Conditions: Type: Mechanism: NO2

Sn /Conc HCl HUR Reduction Not Required. NH2