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
- Aand
- Band
- Cand
- 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