JEE Main · 2020 · 07 Jan 2020 · Shift 2 · Compounds Containing Nitrogen

In the following reaction sequence

The major product B is

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

Answer: (D)

Solution

The

p

-toluidine is first acetylated, turning

- NH X_{2}

into the bulkier

- NHCOCH X_{3}

, which is still an activating, ortho/para directing group. In the bromination step the ring already carries a methyl group and the acetamido group para to one another, so the incoming bromine takes the spot ortho to the small methyl group rather than crowding in next to the bulky acetamido group. The major product B is thus the one brominated ortho to the methyl and para to the acetamido group.

JEE Main · 2020 · 07 Jan 2020 · Shift 2 · Single correct option

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