JEE Main · 2022 · 29 Jun 2022 · Shift 1 · Compounds Containing Nitrogen

Consider the above reaction, the product A and product B respectively are

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

Answer: (C)

Solution

The reaction shows acetanilide undergoing bromination. In acetanilide, the acetamido group (

- NHCOC H_{3}

) is an ortho-para directing activating group. However, it is bulky, so bromination preferentially occurs at the para position. Product A is p-bromoacetanilide. Upon hydrolysis with

H_{3} O^{+}

, the acetyl group is removed, yielding p-bromoaniline as product B. The answer is (C).

JEE Main · 2022 · 29 Jun 2022 · Shift 1 · Single correct option

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