MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition / Nucleophilic acyl substitution of carboxylic acid derivatives
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o1214

Which of the following give a tertiary alcohol when treated with excess (dry ether) followed by ?

  1. Amethyl formate
  2. Bethyl propanoate
  3. Cbutanal
  4. Ddiethyl carbonate

Answer: B, D

Esters other than formates, and carbonates, give tertiary alcohols: ethyl propanoate gives 3-methylpentan-3-ol and diethyl carbonate gives 2-methylpropan-2-ol. Methyl formate gives propan-2-ol (secondary) and butanal gives pentan-2-ol (secondary).
Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Nucleophilic acyl substitution of carboxylic acid derivatives

More questions on Nucleophilic acyl substitution of carboxylic acid derivatives