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Amines

Question
CBSEENCH12009044

Account for the following:
Aniline does not undergo Friedel Craft's reaction.

Solution

a Friedel -crafts reaction is carried out in the presence of AlCl3. but AlCl3 is acidic in nature, while aniline is a strong base. Thus, aniline reacts with AlCl3 to form a salt. Due to the positive charge on the N-atom, electrophilic substitution in the benzene ring is deactivated.Hence, aniline does not under go the Friedel-crafts reactions.

Aniline does not under Friedel-Craft reaction (alkylation and acetylation) due to the salt formation with aluminium chloride, the Lewis acid which is used as a catalyst. Due to this, the nitrogen of aniline acquires a positive charge and hence acts as a strong deactivating group for further reaction.