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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx242

The halide shown is converted to its Grignard reagent with magnesium in dry ether; an excess of the reagent is allowed to react with ethyl ethanoate (ethyl acetate), and the mixture is then hydrolysed with . Which structure is the final product?

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

Answer: B

The first equivalent of propylmagnesium bromide adds to the ester and expels ethoxide, giving pentan-2-one. The ketone is more reactive than the ester, so a second equivalent adds to give a tertiary alkoxide with two propyl groups: 4-methylheptan-4-ol after hydrolysis. Pentan-2-one is the intermediate, 2-methylpentan-2-ol would need a methyl Grignard, and heptan-4-ol would need a formate ester.
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