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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Answer 1

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Chapter 17.1, Problem 3P

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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4. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. 2. 1. LDA 3. H3O+ HO

b. H3C CH3 H3O+ ✓ H OH

2. Provide reagents/conditions to accomplish the following syntheses. More than one step is required in some cases. a. CH3

Answer 2

Question

Chapter 17.1, Problem 3P

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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Answer 3

Question

Chapter 17.1, Problem 3P

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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Answer 4

Question

Chapter 17.1, Problem 3P

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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Answer 5

Chapter 17.1, Problem 3P

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.

Answer 6

Chapter 17.1, Problem 3P

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.

Answer 7

Chapter 17.1, Problem 3P

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.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 17.1 - Prob. 1P Ch. 17.1 - Prob. 2P Ch. 17.1 - Prob. 3P Ch. 17.1 - Prob. 4P Ch. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8P Ch. 17.4 - Prob. 9P Ch. 17.4 - Prob. 10P

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