Chapter 21, Problem 21.58P

Interpretation Introduction

(a)

Interpretation:

The mechanism accounting for the given observations is to be proposed.

Concept introduction:

The ester is hydrolyzed to a carboxylic acid under acidic conditions, so strong base should appear in the mechanism. Water is the nucleophile, and the leaving group is a molecule of ethanol. Proton transfer steps are incorporated to avoid the appearance of strong bases. The bulkier group at O atom in ester prevents the attack of the nucleophile at carbonyl carbon in ester.

Interpretation Introduction

(b)

Interpretation:

Why the each given ester undergoes the proposed mechanism in (a) is to be explained.

Concept introduction:

The ester is hydrolyzed to the carboxylic acid under acidic conditions, so strong base should appear in the mechanism. Water is the nucleophile, and the leaving group is a molecule of ethanol. Proton transfer steps are incorporated to avoid the appearance of strong bases. The bulkier group at O atom in ester prevents the attack of the nucleophile at carbonyl carbon in ester.