JEE Main · 2021 · 31 Aug 2021 · Shift 2 · Compounds Containing Nitrogen

The major products A and B formed in the following reaction sequence are :

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

Answer: (B)

Solution

The amino group of aniline is first protected: with acetic anhydride it forms acetanilide (A),

C_{6} H_{5} NHCOC H_{3}

. The acetamido group is a moderate activator and ortho/para-director, so bromination with

B r_{2}

in acetic acid at room temperature stops cleanly at the para position, giving p-bromoacetanilide (B). So A is acetanilide and B is p-bromoacetanilide.

JEE Main · 2021 · 31 Aug 2021 · Shift 2 · Single correct option

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