Chapter 13, Problem 26P

Interpretation Introduction

Interpretation:

The $\text{α}$ hydrogen of $N,N\text{-disubstituted amide}$ is less acidic than $\text{α}$ hydrogen of an ester has to be explained.

Concept introduction:

Acidity of $\text{α}$ hydrogen that is abstracted by a base depends on the stability of the conjugate base.  If the negative charge on conjugate base is stabilized by resonance or delocalization of electrons, then the loss of $\text{α}$ hydrogen becomes favorable.  More stable the conjugate base, more acidic is the $\text{α}$ hydrogen atom.