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JEE Main 2025 Apr 4 Shift 1, Chemistry Q10: Properties of Amines

JEE Main2025Apr 4, Shift 1Chemistry
Q.

The major product (A) formed in the following reaction sequence is

  1. A

    1

  2. B

    2

  3. C

    3

  4. D

    4

Solution

Step (i) Sn/HCl reduces the nitro group to give aniline.

Step (ii) Acetylation with AcO/pyridine converts NH to NHCOCH (acetanilide). This protection moderates the strong activating, ortho/para-directing NH group so that bromination gives clean monosubstitution rather than 2,4,6-tribromination.

Step (iii) Br/AcOH brominates the ring para to the NHCOCH group (steric crowding at ortho strongly favors para). Product: -bromo-acetanilide.

Step (iv) Aqueous NaOH hydrolyzes the amide back to the free amine.

Final product A: -bromoaniline, matching option (1).

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