(a) Interpretation: An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated. Concept introduction: The Claisen condensation takes place between two esters or between an ester and a ketone . In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester. The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

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Answer 5

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 6

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 7

Chapter 22, Problem 22.28P

Interpretation Introduction

(a)

Interpretation:

An explanation as to why compound A when treated with one equivalent of NaOEt followed by acidification is completely converted to compound B is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the given conversion is to be stated.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The structure of the only product formed when diethyl α- methyladipate reacts in the Dieckmann condensation is to be shown.

Concept introduction:

The Claisen condensation takes place between two esters or between an ester and a ketone. In cross Claisen condensation reaction, the base abstracts an acidic proton from the α-carbon atom of carbonyl compound to form enolate. This enolate reacts with carbonyl group of other carbonyl compound that leads to the formation of β-keto ester.

The intramolecular Claisen condensation in which the product is a five or six member ring is known as Dieckmann condensation.

Answer 12

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Answer 14

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Answer 15

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 how compound A is converted to compound B when treated with NaOEt followed by acidification.

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