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Question:

Account for the following: Aromatic carboxylic acids do not undergo Friedel-Crafts reaction.

Solution:

Aromatic carboxylic acids do not undergo Friedel-Crafts reaction as the carboxyl (−COOH) group is deactivating and Lewis acid catalyst AlCl₃ gets bonded to the carboxyl group. The carboxyl (−COOH) group withdraws electron density from the benzene ring through inductive and resonance effects.