MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms IV: Elimination / E1cB mechanism
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4144

Which observations would support an E1cB(reversible) mechanism over a concerted E2 mechanism for a base-induced elimination?

  1. AUnreacted substrate recovered from has incorporated deuterium at the beta carbon.
  2. BThe rate increases when an electron-withdrawing group that stabilises a carbanion is placed on the beta carbon.
  3. CPoor leaving groups such as are expelled readily.
  4. DThe reaction needs an anti-periplanar arrangement of the beta-H and the leaving group.

Answer: A, B, C

Beta-H/D exchange in recovered substrate, acceleration by carbanion-stabilising groups, and ready loss of poor leaving groups all point to a discrete carbanion. A strict anti-periplanar requirement is characteristic of concerted E2, not E1cB, since the carbanion is a separate intermediate.
Practice Organic Reaction Mechanisms IV: Elimination More on E1cB mechanism

More questions on E1cB mechanism