Friedel-Crafts Reaction Anomaly

Rarely Tested

Aniline does NOT undergo Friedel-Crafts alkylation or acylation because $$\text{C}_6\text{H}_5\text{NH}_2$$ acts as a Lewis base and reacts with the Lewis acid catalyst ($$\text{AlCl}_3$$) to form a salt ($$[\text{C}_6\text{H}_5\text{NH}_2\text{--AlCl}_3]^-$$), deactivating the benzene ring.

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