JEE Main · 2021 · 26 Aug 2021 · Shift 2 · Chapter_pending

The Major Product in the above reaction is:

(A)(see structure)
✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)

Answer: (A)

Solution

Acetic anhydride acetylates whichever nitrogen is still nucleophilic. The

- C H_{2} N H_{2}

group is an ordinary primary aliphatic amine with a freely available lone pair, whereas the nitrogen of the

- CON H_{2}

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,

C H_{3} CONHC H_{2} C_{6} H_{4} CON H_{2}

JEE Main · 2021 · 26 Aug 2021 · Shift 2 · Single correct option

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