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Science Chemistry Organic Chemistry: Principles and Mechanisms (Second Edition)

In Section 15.5c, we learned that the frequency of a C=O stretch decreases when the C=O bond is conjugated to a C=C bond. The pertinent resonance contributor of a conjugated carbonyl ( C=C-C=O ) is to be drawn. Based on the resulting resonance hybrid, the reason for decrease in the frequency is to be explained. Concept introduction: When a C=O group is conjugated to a C=C bond, the frequency of the C=O absorption is typically lowered by 20–40 cm − 1 . The conjugation decreases the stiffness of the C=O bond. If the C=O bond is conjugated to a C=C bond, the resonance structure is possible. The C-O single bond is weaker than C=O bond. The C-O single bond character decreases the stiffness of C=O bond. The stretching frequency of C=O band lowers by the Weakening of C=O bond.

In Section 15.5c, we learned that the frequency of a C=O stretch decreases when the C=O bond is conjugated to a C=C bond. The pertinent resonance contributor of a conjugated carbonyl ( C=C-C=O ) is to be drawn. Based on the resulting resonance hybrid, the reason for decrease in the frequency is to be explained. Concept introduction: When a C=O group is conjugated to a C=C bond, the frequency of the C=O absorption is typically lowered by 20–40 cm − 1 . The conjugation decreases the stiffness of the C=O bond. If the C=O bond is conjugated to a C=C bond, the resonance structure is possible. The C-O single bond is weaker than C=O bond. The C-O single bond character decreases the stiffness of C=O bond. The stretching frequency of C=O band lowers by the Weakening of C=O bond.

Organic Chemistry: Principles and Mechanisms (Second Edition)

Organic Chemistry: Principles and Mechanisms (Second Edition)

2nd Edition

ISBN: 9780393663556

Author: Joel Karty

Publisher: W. W. Norton & Company

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Chapter 15, Problem 15.46P

Interpretation Introduction

Interpretation:

In Section 15.5c, we learned that the frequency of a C=O stretch decreases when the C=O bond is conjugated to a C=C bond. The pertinent resonance contributor of a conjugated carbonyl (C=C-C=O) is to be drawn. Based on the resulting resonance hybrid, the reason for decrease in the frequency is to be explained.

Concept introduction:

When a C=O group is conjugated to a C=C bond, the frequency of the C=O absorption is typically lowered by 20–40 cm−1. The conjugation decreases the stiffness of the C=O bond. If the C=O bond is conjugated to a C=C bond, the resonance structure is possible. The C-O single bond is weaker than C=O bond. The C-O single bond character decreases the stiffness of C=O bond. The stretching frequency of C=O band lowers by the Weakening of C=O bond.

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Chapter 15, Problem 15.45P

Chapter 15, Problem 15.47P

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The first resonance structure of acetamide, CH3 CONH2, is shown. H :0: ☐ || H-C-C-N-H H H Determine the correct second resonance structure of acetamide. H :0: -1 +1 H-C-C-N-H H H H :0: -1 ☐ ☐ H-C=C-N-H H H H :0: H-C-N-C-H HH ●● -1 H:0: H H-C-C=N—H H H

Chapter 15 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 15 - Prob. 15.1P Ch. 15 - Prob. 15.2P Ch. 15 - Prob. 15.3P Ch. 15 - Prob. 15.4P Ch. 15 - Prob. 15.5P Ch. 15 - Prob. 15.6P Ch. 15 - Prob. 15.7P Ch. 15 - Prob. 15.8P Ch. 15 - Prob. 15.9P Ch. 15 - Prob. 15.10P

Ch. 15 - Prob. 15.11P Ch. 15 - Prob. 15.12P Ch. 15 - Prob. 15.13P Ch. 15 - Prob. 15.14P Ch. 15 - Prob. 15.15P Ch. 15 - Prob. 15.16P Ch. 15 - Prob. 15.17P Ch. 15 - Prob. 15.18P Ch. 15 - Prob. 15.19P Ch. 15 - Prob. 15.20P Ch. 15 - Prob. 15.21P Ch. 15 - Prob. 15.22P Ch. 15 - Prob. 15.23P Ch. 15 - Prob. 15.24P Ch. 15 - Prob. 15.25P Ch. 15 - Prob. 15.26P Ch. 15 - Prob. 15.27P Ch. 15 - Prob. 15.28P Ch. 15 - Prob. 15.29P Ch. 15 - Prob. 15.30P Ch. 15 - Prob. 15.31P Ch. 15 - Prob. 15.32P Ch. 15 - Prob. 15.33P Ch. 15 - Prob. 15.34P Ch. 15 - Prob. 15.35P Ch. 15 - Prob. 15.36P Ch. 15 - Prob. 15.37P Ch. 15 - Prob. 15.38P Ch. 15 - Prob. 15.39P Ch. 15 - Prob. 15.40P Ch. 15 - Prob. 15.41P Ch. 15 - Prob. 15.42P Ch. 15 - Prob. 15.43P Ch. 15 - Prob. 15.44P Ch. 15 - Prob. 15.45P Ch. 15 - Prob. 15.46P Ch. 15 - Prob. 15.47P Ch. 15 - Prob. 15.48P Ch. 15 - Prob. 15.49P Ch. 15 - Prob. 15.50P Ch. 15 - Prob. 15.51P Ch. 15 - Prob. 15.52P Ch. 15 - Prob. 15.53P Ch. 15 - Prob. 15.54P Ch. 15 - Prob. 15.55P Ch. 15 - Prob. 15.56P Ch. 15 - Prob. 15.57P Ch. 15 - Prob. 15.58P Ch. 15 - Prob. 15.59P Ch. 15 - Prob. 15.60P Ch. 15 - Prob. 15.61P Ch. 15 - Prob. 15.62P Ch. 15 - Prob. 15.63P Ch. 15 - Prob. 15.64P Ch. 15 - Prob. 15.65P Ch. 15 - Prob. 15.66P Ch. 15 - Prob. 15.67P Ch. 15 - Prob. 15.68P Ch. 15 - Prob. 15.1YT Ch. 15 - Prob. 15.2YT Ch. 15 - Prob. 15.3YT Ch. 15 - Prob. 15.4YT Ch. 15 - Prob. 15.5YT Ch. 15 - Prob. 15.6YT Ch. 15 - Prob. 15.7YT Ch. 15 - Prob. 15.8YT Ch. 15 - Prob. 15.9YT Ch. 15 - Prob. 15.10YT Ch. 15 - Prob. 15.11YT Ch. 15 - Prob. 15.12YT Ch. 15 - Prob. 15.13YT Ch. 15 - Prob. 15.14YT Ch. 15 - Prob. 15.15YT Ch. 15 - Prob. 15.16YT Ch. 15 - Prob. 15.17YT Ch. 15 - Prob. 15.18YT Ch. 15 - Prob. 15.19YT Ch. 15 - Prob. 15.20YT Ch. 15 - Prob. 15.21YT Ch. 15 - Prob. 15.22YT Ch. 15 - Prob. 15.23YT Ch. 15 - Prob. 15.24YT Ch. 15 - Prob. 15.25YT Ch. 15 - Prob. 15.26YT Ch. 15 - Prob. 15.27YT Ch. 15 - Prob. 15.28YT Ch. 15 - Prob. 15.29YT Ch. 15 - Prob. 15.30YT

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