Chapter 18.1, Problem 4P

Interpretation Introduction

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

Concept introduction: Acidity of $\alpha$ 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 $\alpha$ hydrogen becomes favorable.  More stable the conjugate base, more acidic is the $\alpha$ hydrogen atom.