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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1202

Oxolan-2-one (gamma-butyrolactone) is treated with excess in dry ether, then mild aqueous work-up. The product is

  1. A2-methyloxolan-2-ol
  2. B2-methylpentane-2,5-diol
  3. C2,2-dimethyloxolane
  4. D5-hydroxypentan-2-one

Answer: B

The lactone is a cyclic ester. The first opens the ring (alkoxide leaves) to give a methyl ketone bearing a terminal . The ketone adds a second mole, giving a tertiary alkoxide. After work-up: , 2-methylpentane-2,5-diol.
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