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JEE Main levelSingle correct optionDifficulty 2 of 3nc154

Aniline is first treated with / pyridine, then with in glacial acetic acid (one equivalent), and the product is hydrolysed with aqueous acid. The major final product is

  1. A2,4,6-tribromoaniline
  2. B3-bromoaniline
  3. C2-bromoaniline as the only product
  4. D4-bromoaniline

Answer: D

Acetylation converts the strongly activating into the less activating , so monobromination is possible. The bulky acetamido group favours para substitution, giving 4-bromoacetanilide, which on hydrolysis gives 4-bromoaniline.
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