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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc160

Nitrobenzene is converted to aniline (Sn/HCl); aniline is treated with / pyridine; the product is brominated with one equivalent of in acetic acid (major product); the product is hydrolysed with and heat; and then diazotised with / dil. at 273-278 K and treated with . The final compound is

  1. A2-bromobenzonitrile
  2. B3-bromobenzonitrile
  3. C4-bromobenzonitrile
  4. D4-bromobenzoic acid

Answer: C

Sn/HCl gives aniline; acetylation and monobromination give 4-bromoacetanilide (para to the acetamido group); hydrolysis gives 4-bromoaniline. Diazotisation and the Sandmeyer cyanation then replace by CN, giving 4-bromobenzonitrile. The nitrile is not hydrolysed under these conditions.
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