Question

Aniline does not undergo Friedel-Crafts reaction. Choose the correct option(s) regarding this statement.

• A. Aniline forms salt with the Lewis acid catalyst i.e., AlCl₃, which is used in Friedel-Crafts reaction.
• B. Nitrogen of aniline acquires positive charge and hence acts as a strong deactivating group for further reaction.
• C. N-alkyl and N,N-dialkyl anilines undergo Friedel-Craft's reactions.
• D. Positive charge on nitrogen is electron-donating and it activates the ring for further reactions.

Answer 1

Answer: (A), (B)

Nitrogen of aniline acquires positive charge and hence acts as a strong deactivating group for further reaction.

Aniline, N-substituted and N,N-disubstituted anilines do not undergo Friedel-Craft's reactions due to salt formation with aluminium chloride which is used as a Lewis acid catalyst. Positive charge on nitrogen is strongly electron-withdrawing and thus deactivates the ring for further acylation or alkylation reactions.