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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4087

Which of the following reactions proceed through a carbanion intermediate formed by deprotonation (E1cB mechanism)?

  1. A3-hydroxybutanal, , with aqueous on warming
  2. B2-bromo-2-methylpropane with in ethanol
  3. C4-hydroxy-4-methylpentan-2-one with on heating (giving mesityl oxide)
  4. D1-bromopropane with in ethanol giving propene

Answer: A, C

E1cB occurs when a beta hydrogen is acidic and the leaving group is poor. The hydrogens alpha to the carbonyl group in the two beta-hydroxy carbonyl compounds are acidic, and hydroxide is a poor leaving group, so an enolate (carbanion) forms first and then expels . The two alkyl bromides have good leaving groups and non-acidic hydrogens, so they react by concerted E2.
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