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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o1164

Which of the following statements about acetal formation from an aldehyde and an alcohol are correct?

  1. AAcid is needed for hemiacetal to acetal conversion because the OH must be converted into a better leaving group.
  2. B in converts an aldehyde fully into its dimethyl acetal.
  3. CThe oxocarbenium ion intermediate is stabilised by donation of an oxygen lone pair.
  4. DAcyclic simple hemiacetals are generally in equilibrium with the carbonyl compound and are not isolated.

Answer: A, C, D

Hemiacetals revert easily. Hydroxide or alkoxide are very poor leaving groups, so in base the reaction stops at the hemiacetal, while in acid leaves, giving an oxocarbenium ion stabilised by oxygen. Hence base does not give acetals.
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