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JEE Advanced levelSingle correct optionDifficulty 3 of 3si213

Phthalimide is treated with KOH to give A. A is heated with bromoethane to give B. B is hydrolysed with aqueous NaOH (heat) to give amine C. C is heated with and alcoholic KOH to give D. D is

  1. A
  2. B
  3. C
  4. D

Answer: D

The Gabriel synthesis gives ethanamine (C), a primary amine, from N-ethylphthalimide. Primary amines give the carbylamine reaction with , forming the foul-smelling ethyl isocyanide, . The nitrile is a different compound.
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