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JEE Main levelSingle correct optionDifficulty 2 of 3o1254

The ester shown is reduced with an excess of lithium aluminium hydride, followed by aqueous work-up. Which product(s) are formed?

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

Answer: C

Ethyl ethanoate is reduced by two hydride equivalents: the first gives a tetrahedral intermediate that expels ethoxide to form ethanal, which is reduced at once to ethoxide. The acyl portion becomes ethanol and the alkoxy portion is released as ethanol, so two molecules of ethanol result. Ethanal is not isolated.
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