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Chapter 12: Reactions of Arenes. Electrophilic Aromatic Substitution



Summary | Overview | Nitration | Sulfonation | Halogenation | Friedel-Crafts Alkylation | Friedel-Crafts Acylation | Substituent Effects | Making Polysubstituted Benzenes | Polyaromatics | Heterocycles | Self Assessment | Quiz |


Nitration

Chapter 12 : Reactions of Arenes. Electrophilic Aromatic Substitution

Nitration of Benzene

nitration of arenes
Reaction type: Electrophilic Aromatic Substitution

Summary.


 
MECHANISM FOR NITRATION OF BENZENE
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.



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