Given that 2-substituted-2-cyclopentenones are in a base catalyzed equilibrium with their 5-substituted-2-cyclopentenone isomers. Why such analogous isomerization is not observed for 2-substituted -2-cyclohexenones is to be explained. Concept introduction: The isomerization of cycloalkenones occurs through an enolate anion formed by the abstraction of acidic hydrogen by the base. Hydrogens on carbon α- to a carbonyl group and those on γ- carbon in a conjugated enone are acidic. If these hydrogens are removed, isomerization will occur. Otherwise isomerization is not possible. To explain: Why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 6-substituted -2-cyclohexenone isomers like 2-substituted-2-cyclopentenones.

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Answer 1

Question

Chapter 22.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that 2-substituted-2-cyclopentenones are in a base catalyzed equilibrium with their 5-substituted-2-cyclopentenone isomers. Why such analogous isomerization is not observed for 2-substituted -2-cyclohexenones is to be explained.

Concept introduction:

The isomerization of cycloalkenones occurs through an enolate anion formed by the abstraction of acidic hydrogen by the base. Hydrogens on carbon α- to a carbonyl group and those on γ- carbon in a conjugated enone are acidic. If these hydrogens are removed, isomerization will occur. Otherwise isomerization is not possible.

To explain:

Why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 6-substituted -2-cyclohexenone isomers like 2-substituted-2-cyclopentenones.

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Answer 2

Question

Chapter 22.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that 2-substituted-2-cyclopentenones are in a base catalyzed equilibrium with their 5-substituted-2-cyclopentenone isomers. Why such analogous isomerization is not observed for 2-substituted -2-cyclohexenones is to be explained.

Concept introduction:

The isomerization of cycloalkenones occurs through an enolate anion formed by the abstraction of acidic hydrogen by the base. Hydrogens on carbon α- to a carbonyl group and those on γ- carbon in a conjugated enone are acidic. If these hydrogens are removed, isomerization will occur. Otherwise isomerization is not possible.

To explain:

Why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 6-substituted -2-cyclohexenone isomers like 2-substituted-2-cyclopentenones.

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Answer 3

Question

Chapter 22.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that 2-substituted-2-cyclopentenones are in a base catalyzed equilibrium with their 5-substituted-2-cyclopentenone isomers. Why such analogous isomerization is not observed for 2-substituted -2-cyclohexenones is to be explained.

Concept introduction:

The isomerization of cycloalkenones occurs through an enolate anion formed by the abstraction of acidic hydrogen by the base. Hydrogens on carbon α- to a carbonyl group and those on γ- carbon in a conjugated enone are acidic. If these hydrogens are removed, isomerization will occur. Otherwise isomerization is not possible.

To explain:

Why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 6-substituted -2-cyclohexenone isomers like 2-substituted-2-cyclopentenones.

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Answer 4

Question

Chapter 22.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that 2-substituted-2-cyclopentenones are in a base catalyzed equilibrium with their 5-substituted-2-cyclopentenone isomers. Why such analogous isomerization is not observed for 2-substituted -2-cyclohexenones is to be explained.

Concept introduction:

The isomerization of cycloalkenones occurs through an enolate anion formed by the abstraction of acidic hydrogen by the base. Hydrogens on carbon α- to a carbonyl group and those on γ- carbon in a conjugated enone are acidic. If these hydrogens are removed, isomerization will occur. Otherwise isomerization is not possible.

To explain:

Why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 6-substituted -2-cyclohexenone isomers like 2-substituted-2-cyclopentenones.

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Answer 5

Chapter 22.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that 2-substituted-2-cyclopentenones are in a base catalyzed equilibrium with their 5-substituted-2-cyclopentenone isomers. Why such analogous isomerization is not observed for 2-substituted -2-cyclohexenones is to be explained.

Concept introduction:

The isomerization of cycloalkenones occurs through an enolate anion formed by the abstraction of acidic hydrogen by the base. Hydrogens on carbon α- to a carbonyl group and those on γ- carbon in a conjugated enone are acidic. If these hydrogens are removed, isomerization will occur. Otherwise isomerization is not possible.

To explain:

Why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 6-substituted -2-cyclohexenone isomers like 2-substituted-2-cyclopentenones.

Answer 6

Chapter 22.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that 2-substituted-2-cyclopentenones are in a base catalyzed equilibrium with their 5-substituted-2-cyclopentenone isomers. Why such analogous isomerization is not observed for 2-substituted -2-cyclohexenones is to be explained.

Concept introduction:

The isomerization of cycloalkenones occurs through an enolate anion formed by the abstraction of acidic hydrogen by the base. Hydrogens on carbon α- to a carbonyl group and those on γ- carbon in a conjugated enone are acidic. If these hydrogens are removed, isomerization will occur. Otherwise isomerization is not possible.

To explain:

Why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 6-substituted -2-cyclohexenone isomers like 2-substituted-2-cyclopentenones.

Answer 7

Chapter 22.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that 2-substituted-2-cyclopentenones are in a base catalyzed equilibrium with their 5-substituted-2-cyclopentenone isomers. Why such analogous isomerization is not observed for 2-substituted -2-cyclohexenones is to be explained.

Concept introduction:

The isomerization of cycloalkenones occurs through an enolate anion formed by the abstraction of acidic hydrogen by the base. Hydrogens on carbon α- to a carbonyl group and those on γ- carbon in a conjugated enone are acidic. If these hydrogens are removed, isomerization will occur. Otherwise isomerization is not possible.

To explain:

Why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 6-substituted -2-cyclohexenone isomers like 2-substituted-2-cyclopentenones.

Answer 8

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Answer 10

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Answer 11

Ch. 22.1 - Prob. 1P Ch. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3P Ch. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5P Ch. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7P Ch. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P

Solution Summary: The author explains why 2-substituted -2-cyclohexenones are not in a base catalyzed equilibrium with their 5 substituents.

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Chapter 22 Solutions