Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 13.1, Problem 4P
Interpretation Introduction

Interpretation: Remove a proton from the alpha carbon of N,N-dimethylethanamide but not from the alpha carbon of either N-methylethanamide or ethanamide has to be explained.

Concept introduction: The electrons left behind when a proton is removed from the alpha carbon of an amide are not readily delocalized.  This is because the nitrogen of the NR group of an amide also has a lone-pair that can be delocalized on to the carbonyl oxygen.

Thus the lone pair on the alpha carbon and the lone pair on the nitrogen compete for the delocalization onto the same oxygen.

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What is the correct IUPAC name for the following molecule? ON-ethyl-N-methyl-2-propyl cyclohexanamine O N-ethyl-N-methyl-6-propyl cyclohexanamine IN ON-ethyl-N-methyl-1-propyl-2-cyclohexanamine ⒸN-cthyl-N-methyl-2-propyl-N-cyclohexanamine Previous Next
Explain why a base can remove a proton from the alpha-carbon of N,N-dimethylethanamide but not from the alpha-carbon of either N-methylethanamide or ethanamide.
Select the name for each amide. ye N-ethylpropanamide N-methylbutanamide N-butylethanamide N-ethylbutanamide 4-cyclopentylbutanamide 5-cyclopentylpentanamide O cyclopentylbutanamide butanamide cyclopentane N-butylethanamide N-diethylacetamide N,N-diethylethanamide N,N-dimethylacetamide N-ethyl.N-methylbenzoate ON-ethyl,N-methyl-2-phenylpropanamide N-ethyl-N-methyl-2-phenylethanamide N,N-diethylbenzoate

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