Chapter 21.SE, Problem 67AP

Interpretation Introduction

Interpretation:

To predict the reactivity order of the following basic hydrolysis of p-substituted methyl benzoates.

Concept introduction:

Y = NO₂ > Br > H > CH₃ > OCH₃

Is explained on the basis of the extent of electron withdrawal at the para position by these groups, which increases the electron deficiency of the carbonyl carbon of the acyl functional group. The greater this electron deficiency, the more readily, the nucleophile attacks this carbonyl carbon; all other factors of leaving group, solvent etc, remaining constant.