MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms IV: Elimination / E1cB mechanism
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4053

Which of the following can undergo dehydration with dilute by the E1cB mechanism?

  1. A3-hydroxybutanal
  2. B (3-hydroxy-2,2-dimethylpropanal)
  3. C4-hydroxy-4-methylpentan-2-one
  4. D3-hydroxycyclohexan-1-one

Answer: A, C, D

E1cB dehydration requires an alpha-hydrogen on the carbon between C=O and the beta-carbon that bears the OH. 3-Hydroxybutanal, 4-hydroxy-4-methylpentan-2-one and 3-hydroxycyclohexanone all have such an alpha-H (the last gives cyclohex-2-enone). In the alpha-carbon is quaternary and has no hydrogen, so no enolate can form.
Practice Organic Reaction Mechanisms IV: Elimination More on E1cB mechanism

More questions on E1cB mechanism