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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1160

4-Acetylbenzaldehyde, , is treated in sequence with (i) one equivalent of ethylene glycol, dry ; (ii) (1 equiv), dry ether; (iii) dilute . The final product is

  1. A4-(1-hydroxyethyl)acetophenone
  2. B1,1'-(1,4-phenylene)bis(ethanol)
  3. C4-acetylbenzoic acid
  4. D4-(2-hydroxypropan-2-yl)benzaldehyde

Answer: D

The aldehyde, which is more reactive than the ketone toward acetal formation, is protected as the cyclic acetal. then adds to the ketone to give a tertiary alkoxide, . Aqueous acid removes the acetal, giving .
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