Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
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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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE
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Chapter 13 Solutions

Essential Organic Chemistry (3rd Edition)

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