Return to Contents
Chapter 12 : 
Reactions of Arenes. Electrophilic Aromatic Substitution
Ch 12 contents

Nitration of Benzene

nitration of arenes

Reaction type: Electrophilic Aromatic Substitution


Step 1:
An acid / base reaction. Protonation of the hydroxy group of the nitric acid. This provides a better leaving group.....
nitration of benzene

Step 2:
Loss of the leaving group, a water molecule provides the nitronium ion, the reactive electrophile.
Step 3:
The electrophilic nitronium ion reacts with the nucleophilic C=C of the arene. This is the rate determining step as it destroys the aromaticity of the arene.
Step 4:
Water functions as a base to remove the proton from the sp3 C bearing the nitro- group and reforms the C=C and the aromatic system.


previous page
next page
organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary