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JEE Main levelSingle correct optionDifficulty 2 of 3co025

Ethyl benzoate is treated with one equivalent of DIBAL-H in toluene at 195 K, followed by aqueous work-up. The main product is

  1. Abenzene
  2. Bbenzaldehyde
  3. Cbenzyl alcohol
  4. Dbenzoic acid

Answer: B

At low temperature DIBAL-H delivers a single hydride to the ester and the tetrahedral intermediate is stable until work-up. Hydrolysis then gives and ethanol. Benzyl alcohol would form with or at higher temperature.
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