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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx257

The bromide shown is heated with and the product is reduced with over Ni. Which structure is the final product?

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

Answer: A

AgCN gives the isocyanide, ethyl isocyanide (N-bonded). Catalytic hydrogenation reduces the isocyanide carbon to a methyl group on nitrogen: , giving N-methylethanamine (a secondary amine). Propylamine would be the reduced KCN nitrile, and the other amines have the wrong carbon skeleton.
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