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JEE Main levelSingle correct optionDifficulty 2 of 3hx256

The bromide shown is treated with in aqueous ethanol and the product is then boiled with dilute . Which structure is the final organic product?

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

Answer: A

KCN gives the nitrile (3-methylbutanenitrile, one carbon more than the bromide) by SN2 at the primary carbon. Complete acid hydrolysis converts the cyano group to a carboxylic acid: 3-methylbutanoic acid. The amide is the partial hydrolysis product; 2-methylpropanoic acid would need loss of a carbon.
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