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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1261

The lactone shown is treated with an excess of methylmagnesium bromide, followed by aqueous work-up. Which structure is the product?

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

Answer: D

Butyrolactone is a cyclic ester. The first Grignard equivalent opens the ring to give a ketone and a primary alkoxide; the ketone is more reactive than the ester and adds a second methyl group, giving a tertiary alkoxide. After work-up the product is 4-methylpentane-1,4-diol, with one primary and one tertiary OH.
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