Acetic anhydride acetylates whichever nitrogen is still nucleophilic. The −CH2NH2 group is an ordinary primary aliphatic amine with a freely available lone pair, whereas the nitrogen of the −CONH2 group has its lone pair delocalised onto the carbonyl oxygen and is a very poor nucleophile. Acylation therefore takes place only at the benzylic amine and the amide survives unchanged. The major product is 3-(acetamidomethyl)benzamide, CH3CONHCH2C6H4CONH2.
JEE Main · 2021 · 26 Aug 2021 · Shift 2 · Single correct option