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Aniline reacts with acetic anhydride in pyridine to give a product which reacts with Br2 in CH3COOH to get

  • A.o-bromoaniline
  • B.p-bromoaniline
  • C.p-bromoacetanilide
  • D.o-bromoacetanilide
  • E.m-bromoacetanilide

Answer: C

The product is p-bromoacetanilide.

Acetic anhydride in pyridine acetylates aniline to acetanilide, C6H5NHCOCH3. The acetyl group makes the nitrogen's lone pair less available to the ring, so the ring is only moderately activated, and bromination in acetic acid gives a single substitution, mainly at the para position (the bulky NHCOCH3 group hinders the ortho positions).

The bromoaniline options leave out the acetyl group, which stays on until the amide is hydrolysed in a separate step. o-Bromoacetanilide is the minor product, and the meta isomer is not formed because NHCOCH3 directs ortho and para.

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