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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1201

Diethyl carbonate, , is treated with excess , then . The final product is

  1. Apentan-3-one
  2. Bethyl propanoate
  3. C3-ethylpentan-3-ol
  4. Dpentan-3-ol

Answer: C

Three C-O/C=O links are replaced in succession: the first expels ethoxide to give ethyl propanoate, the second gives pentan-3-one, the third gives . Hydrolysis gives 3-ethylpentan-3-ol, which uses 3 mol of Grignard.
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