(a) Interpretation: The curved-arrow mechanism for the reaction of 2-oxocyclohexanal with but-3-en-2-one is to be stated. The intermediate A has to be identified. Concept introduction: Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β- unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β- hydroxyl aldehydes or β- hydroxyl ketones.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.49P

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the reaction of 2-oxocyclohexanal with but-3-en-2-one is to be stated. The intermediate A has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β- unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β- hydroxyl aldehydes or β- hydroxyl ketones.

Interpretation Introduction

(b)

Interpretation:

The curved-arrow mechanism for the reaction of diethyl malonate with but-3-en-2-one is to be stated. The intermediate has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β− unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β− hydroxyl aldehydes or β− hydroxyl ketones.

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Students have asked these similar questions

a) Which base would be the best base to use for both of these and why? b) Give the expected product for the Claisen condensation reaction of A). c) Compound A) will successfully undergo a Claisen condensation reaction, however, Compound B) will not. Briefly explain why, and show the form of the product for Compound A) that makes the reaction possible.

Propose a curved arrow mechanism to account for the formation of compound C.

(b) Classify the following alcohols in order of increasing ease of acid-catalyzed dehydration.Justify your answers.

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.49P

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the reaction of 2-oxocyclohexanal with but-3-en-2-one is to be stated. The intermediate A has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β- unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β- hydroxyl aldehydes or β- hydroxyl ketones.

Interpretation Introduction

(b)

Interpretation:

The curved-arrow mechanism for the reaction of diethyl malonate with but-3-en-2-one is to be stated. The intermediate has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β− unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β− hydroxyl aldehydes or β− hydroxyl ketones.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.49P

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the reaction of 2-oxocyclohexanal with but-3-en-2-one is to be stated. The intermediate A has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β- unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β- hydroxyl aldehydes or β- hydroxyl ketones.

Interpretation Introduction

(b)

Interpretation:

The curved-arrow mechanism for the reaction of diethyl malonate with but-3-en-2-one is to be stated. The intermediate has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β− unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β− hydroxyl aldehydes or β− hydroxyl ketones.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.49P

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the reaction of 2-oxocyclohexanal with but-3-en-2-one is to be stated. The intermediate A has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β- unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β- hydroxyl aldehydes or β- hydroxyl ketones.

Interpretation Introduction

(b)

Interpretation:

The curved-arrow mechanism for the reaction of diethyl malonate with but-3-en-2-one is to be stated. The intermediate has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β− unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β− hydroxyl aldehydes or β− hydroxyl ketones.

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Answer 5

Chapter 22, Problem 22.49P

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the reaction of 2-oxocyclohexanal with but-3-en-2-one is to be stated. The intermediate A has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β- unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β- hydroxyl aldehydes or β- hydroxyl ketones.

Interpretation Introduction

(b)

Interpretation:

The curved-arrow mechanism for the reaction of diethyl malonate with but-3-en-2-one is to be stated. The intermediate has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β− unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β− hydroxyl aldehydes or β− hydroxyl ketones.

Answer 6

Chapter 22, Problem 22.49P

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the reaction of 2-oxocyclohexanal with but-3-en-2-one is to be stated. The intermediate A has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β- unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β- hydroxyl aldehydes or β- hydroxyl ketones.

Answer 7

Chapter 22, Problem 22.49P

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the reaction of 2-oxocyclohexanal with but-3-en-2-one is to be stated. The intermediate A has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β- unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β- hydroxyl aldehydes or β- hydroxyl ketones.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The curved-arrow mechanism for the reaction of diethyl malonate with but-3-en-2-one is to be stated. The intermediate has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β− unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β− hydroxyl aldehydes or β− hydroxyl ketones.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The curved-arrow mechanism for the reaction of diethyl malonate with but-3-en-2-one is to be stated. The intermediate has to be identified.

Concept introduction:

Michael addition reactions are those reactions in which an enolate ion undergoes cyclo-addition reactions with α,β− unsaturated carbonyl compounds. This reaction occurs in the presence of a catalytic base. Aldol condensation reactions are those reactions in which enolate ions reacts with carbonyl compounds to produce β− hydroxyl aldehydes or β− hydroxyl ketones.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 22 - Prob. 22.1P Ch. 22 - Prob. 22.2P Ch. 22 - Prob. 22.3P Ch. 22 - Prob. 22.4P Ch. 22 - Prob. 22.5P Ch. 22 - Prob. 22.6P Ch. 22 - Prob. 22.7P Ch. 22 - Prob. 22.8P Ch. 22 - Prob. 22.9P Ch. 22 - Prob. 22.10P

Solution Summary: The author explains the curved-arrow mechanism for the reaction of 2-oxocyclohexanal and the intermediate A.

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Chapter 22 Solutions