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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc273

The aromatic amine shown is diazotised at 0-5 C, the product is treated with , and the resulting nitrile is hydrolysed with aqueous acid and heat. Which structure is the final product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

The compound shown is 2-methylaniline (o-toluidine). The Sandmeyer cyanation gives 2-methylbenzonitrile (the nitrile carbon is directly on the ring). Acid hydrolysis converts the nitrile through the amide to the carboxylic acid, 2-methylbenzoic acid; no extra carbon is added in the hydrolysis.
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