The side reaction that would occur in the condensation of ethyl acetate with sodium methoxide base is to be predicted. 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.

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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 22.12, Problem 22.34P

(a)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium methoxide base is to be predicted.

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.

(b)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium hydroxide base is to be predicted.

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.

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Students have asked these similar questions

what is the purpose of addition of acid during the reaction

Ethoxide is used as the base in the condensation of ethyl acetate to avoid some unwantedside reactions. Show what side reactions would occur if the following bases were used.(a) sodium methoxide

show the reagents used to get to the product

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 22.12, Problem 22.34P

(a)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium methoxide base is to be predicted.

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.

(b)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium hydroxide base is to be predicted.

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.

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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 22.12, Problem 22.34P

(a)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium methoxide base is to be predicted.

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.

(b)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium hydroxide base is to be predicted.

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.

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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 22.12, Problem 22.34P

(a)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium methoxide base is to be predicted.

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.

(b)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium hydroxide base is to be predicted.

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.

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Answer 5

Chapter 22.12, Problem 22.34P

(a)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium methoxide base is to be predicted.

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.

(b)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium hydroxide base is to be predicted.

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 6

Chapter 22.12, Problem 22.34P

(a)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium methoxide base is to be predicted.

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 7

Chapter 22.12, Problem 22.34P

(a)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium methoxide base is to be predicted.

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 8

(b)

Interpretation Introduction

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium hydroxide base is to be predicted.

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

Interpretation:

The side reaction that would occur in the condensation of ethyl acetate with sodium hydroxide base is to be predicted.

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

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Answer 12

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Answer 13

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 explains the side reaction that occurs in the condensation of ethyl acetate with sodium hydroxide base.

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