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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap013

An ester of formula is treated with excess and then . The only organic product is propan-2-ol. The ester is

  1. Apropyl methanoate
  2. Bisopropyl methanoate
  3. Cethyl ethanoate
  4. Dmethyl propanoate

Answer: B

A formate ester with excess Grignard reagent gives a secondary alcohol from the acyl part: gives . For only propan-2-ol to form, the alkoxy part must also be isopropyl. So the ester is . Propyl methanoate would also give propan-1-ol; ethyl ethanoate gives 2-methylpropan-2-ol and ethanol.
Practice Alcohols, Phenols and Ethers More on Preparation of alcohols including from carbonyls and Grignard

More questions on Preparation of alcohols including from carbonyls and Grignard