EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 13, Problem 26P
Interpretation Introduction

Interpretation:

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

Concept introduction:

Acidity of 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 α hydrogen becomes favorable.  More stable the conjugate base, more acidic is the α hydrogen atom.

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