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Aniline does not undergo Friedel - Craft...

Aniline does not undergo Friedel - Crafts reaction. Explain.

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Aniline being a Lewis base with Lewis acid `AlCl_(3)` to form a salt.

Due to the presence of a positive charge on N-atom in the salt the group `-overset(+)NH_(2)AlCl_(3)^(-)` acts as a strongly deactivating group. As a result, it reduces the electron density in the benzene ring and which inhibits the electrophilic substitution reaction. Therefore aniline does not undergo Friedel - Crafts reaction.
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