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JEE Main levelSingle correct optionDifficulty 2 of 3o1253

Which of the structures shown has a larger equilibrium constant for hydration (carbonyl to gem-diol) than the aldehyde shown?

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

Answer: B

Electron-withdrawing groups destabilise the carbonyl and stabilise the gem-diol. Trichloroethanal (chloral) has a strongly withdrawing CCl3 group and forms a stable crystalline hydrate, so its K for hydration is far larger than for benzaldehyde. The ketones and 4-methoxybenzaldehyde have more stabilised carbonyl groups (alkyl, conjugation or +M donation) and hydrate less.
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