Quantrex Quantrex AcademyJEE · NEET · NDA PYQs with solutions Open app
Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives

Consider the acid-catalyzed hydrolysis of the ¹⁸ O -labeled ester shown below: Identify the major products A (an acid) and B.

Options

  1. Aand
  2. Band
  3. Cand
  4. Dand

Correct answer

A. and

Step-by-step solution

The given ester is formed from acetic acid and a tertiary alcohol (2-phenylpropan-2-ol). In the acid-catalyzed hydrolysis of esters, the mechanism depends on the nature of the alkyl group. For esters with primary or secondary alkyl groups, the reaction typically proceeds via the A_ AC 2 mechanism (acyl-oxygen cleavage). However, when the alkyl group can form a highly stable carbocation (such as a tertiary, allylic, or benzylic carbocation), the reaction proceeds via the A_ AL 1 mechanism (alkyl-oxygen cleavage). In

Practice Carboxylic Acid Derivatives on Quantrex Academy →

More from Carboxylic Acid Derivatives

All Carboxylic Acid Derivatives questions Full Carboxylic Acid Derivatives list All Fundamentals of Organic Chemistry PYQs