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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc197

Aniline is treated in sequence with (i) / pyridine, (ii) one equivalent of in acetic acid (major product), (iii) acid hydrolysis, (iv) / dil. at 273-278 K, (v) . The final product is

  1. A2,4,6-tribromobenzonitrile
  2. B3-bromobenzonitrile
  3. C2-bromobenzonitrile
  4. D4-bromobenzonitrile

Answer: D

Step (i) protects the amine as acetanilide; step (ii) brominates mainly para to the acetamido group; step (iii) restores 4-bromoaniline; (iv) gives 4-bromobenzenediazonium chloride; (v) Sandmeyer cyanation replaces the diazonium group by CN. The bromine is untouched, giving 4-bromobenzonitrile.
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