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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc161

4-Methylbenzamide is treated with to give P; P is treated with / pyridine to give Q; Q is brominated with one equivalent of in acetic acid to give R (major product); and R is hydrolysed with aqueous acid and heat to give S. S is

  1. A3-bromo-4-methylaniline
  2. B2-bromo-4-methylaniline
  3. C2,6-dibromo-4-methylaniline
  4. D4-bromo-2-methylaniline

Answer: B

Hofmann bromamide degradation removes the carbonyl carbon, giving P = 4-methylaniline. Acetylation gives Q = N-(4-methylphenyl)acetamide. The acetamido group is a stronger director than CH3 and Br enters ortho to it, giving R. Hydrolysis then gives S = 2-bromo-4-methylaniline.
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