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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx246

The halide shown is converted to its Grignard reagent with magnesium in dry ether; benzonitrile () is added, and the mixture is then heated with aqueous acid. Which structure is the final product?

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

Answer: A

The Grignard reagent adds once to the polarised C#N bond to give a magnesium imine salt (it cannot add again because the anion is unreactive); aqueous acid hydrolyses the imine to a ketone. Butylmagnesium bromide therefore gives valerophenone (1-phenylpentan-1-one). The amine is a reduction product, the secondary alcohol would come from benzaldehyde, and the acid from hydrolysis of the nitrile alone.
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