The synthesis of the given compound with the help of an aldol, claisen or another type of condensation. Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized. Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β − hydroxy ketone or aldehyde . The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

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Answer 1

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 22.68SP

(a)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

(b)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

(c)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Intramolecular aldol reactions of diketones are used for the formation of five and six membered rings. These reactions are known as aldol cyclizations. Aldol cyclization of rings which are larger than six and smaller than five is less common.

(d)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(e)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(f)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

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7. Draw the mechanism to describe the following transformation: Note: This is a base catalyzed reaction. So, the last steps must make [OH]- OH [OH]¯ OH Heat O

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Answer 2

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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 22.68SP

(a)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

(b)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

(c)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Intramolecular aldol reactions of diketones are used for the formation of five and six membered rings. These reactions are known as aldol cyclizations. Aldol cyclization of rings which are larger than six and smaller than five is less common.

(d)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(e)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(f)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

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Answer 3

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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 22.68SP

(a)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

(b)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

(c)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Intramolecular aldol reactions of diketones are used for the formation of five and six membered rings. These reactions are known as aldol cyclizations. Aldol cyclization of rings which are larger than six and smaller than five is less common.

(d)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(e)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(f)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

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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 22.68SP

(a)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

(b)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

(c)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Intramolecular aldol reactions of diketones are used for the formation of five and six membered rings. These reactions are known as aldol cyclizations. Aldol cyclization of rings which are larger than six and smaller than five is less common.

(d)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(e)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(f)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

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Answer 5

Chapter 22, Problem 22.68SP

(a)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

(b)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

(c)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Intramolecular aldol reactions of diketones are used for the formation of five and six membered rings. These reactions are known as aldol cyclizations. Aldol cyclization of rings which are larger than six and smaller than five is less common.

(d)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(e)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

(f)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

Answer 6

Chapter 22, Problem 22.68SP

(a)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

Answer 7

Chapter 22, Problem 22.68SP

(a)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

Answer 8

(b)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

Answer 9

(b)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: In the claisen-ester condensation, nucleophilic acyl substitution takes place on an ester. The enolate ion acts as a nucleophile. It attacks the carbonyl carbon to form a tetrahedral intermediate. Acidity of beta-keto ester products is higher than simple ketones, aldehydes and esters.

Answer 10

(c)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Intramolecular aldol reactions of diketones are used for the formation of five and six membered rings. These reactions are known as aldol cyclizations. Aldol cyclization of rings which are larger than six and smaller than five is less common.

Answer 11

(c)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Intramolecular aldol reactions of diketones are used for the formation of five and six membered rings. These reactions are known as aldol cyclizations. Aldol cyclization of rings which are larger than six and smaller than five is less common.

Answer 12

(d)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

Answer 13

(d)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

Answer 14

(e)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

Answer 15

(e)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

Answer 16

(f)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

Answer 17

(f)

Interpretation Introduction

To determine: The synthesis of the given compound with the help of an aldol, claisen or another type of condensation.

Interpretation: The given compound with the help of an aldol, claisen or another type of condensation is to be synthesized.

Concept introduction: Condensation reaction that takes place between two carbonyl group containing molecules involves both nucleophilic addition and alpha substitution. Such a condensation reaction is known as carbonyl condensation reaction. One carbonyl is converted into a nucleophilic enolate ion by a base in this reaction.

Answer 18

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Answer 19

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Answer 20

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Answer 21

Ch. 22.2A - Prob. 22.2P Ch. 22.4 - Without looking back, propose a mechanism for the...Ch. 22.4 - Prob. 22.8P Ch. 22.4 - Prob. 22.9P Ch. 22.5A - Prob. 22.10P Ch. 22.5A - Prob. 22.11P Ch. 22.5B - Prob. 22.12P Ch. 22.5B - Predict the products of the following reactions....Ch. 22.5B - Which compounds will give positive iodoform tests?...Ch. 22.5C - Propose a mechanism for the acid-catalyzed...

Solution Summary: The author defines aldol condensation as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group.

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Chapter 22 Solutions