(a) Interpretation: How the given transformation can be carried out is to be determined. Concept introduction: Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester.

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Answer 1

Question

Chapter 20, Problem 20.32P

Interpretation Introduction

(a)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester.

Interpretation Introduction

(b)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester. Under the basic conditions, the acid is immediately (irreversibly) deprotonated to the carboxylate anion. The carboxylic acid can be recovered by acid workup.

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Answer 2

Question

Chapter 20, Problem 20.32P

Interpretation Introduction

(a)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester.

Interpretation Introduction

(b)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester. Under the basic conditions, the acid is immediately (irreversibly) deprotonated to the carboxylate anion. The carboxylic acid can be recovered by acid workup.

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Answer 3

Question

Chapter 20, Problem 20.32P

Interpretation Introduction

(a)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester.

Interpretation Introduction

(b)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester. Under the basic conditions, the acid is immediately (irreversibly) deprotonated to the carboxylate anion. The carboxylic acid can be recovered by acid workup.

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Answer 4

Question

Chapter 20, Problem 20.32P

Interpretation Introduction

(a)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester.

Interpretation Introduction

(b)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester. Under the basic conditions, the acid is immediately (irreversibly) deprotonated to the carboxylate anion. The carboxylic acid can be recovered by acid workup.

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Answer 5

Chapter 20, Problem 20.32P

Interpretation Introduction

(a)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester.

Interpretation Introduction

(b)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester. Under the basic conditions, the acid is immediately (irreversibly) deprotonated to the carboxylate anion. The carboxylic acid can be recovered by acid workup.

Answer 6

Chapter 20, Problem 20.32P

Interpretation Introduction

(a)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester.

Answer 7

Chapter 20, Problem 20.32P

Interpretation Introduction

(a)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester. Under the basic conditions, the acid is immediately (irreversibly) deprotonated to the carboxylate anion. The carboxylic acid can be recovered by acid workup.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How the given transformation can be carried out is to be determined.

Concept introduction:

Esters undergo a substitution of the alkoxide group by another alkoxide in a reaction known as transesterification. Although it appears to be a substitution reaction, the mechanism consists of two steps – nucleophilic addition of the incoming alkoxide ion at the carbonyl carbon, followed by elimination of the original alkoxide group. In effect, this substitutes the original alkoxide group in the ester by another, giving a different ester. Under the basic conditions, the acid is immediately (irreversibly) deprotonated to the carboxylate anion. The carboxylic acid can be recovered by acid workup.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 20 - Prob. 20.1P Ch. 20 - Prob. 20.2P Ch. 20 - Prob. 20.3P Ch. 20 - Prob. 20.4P Ch. 20 - Prob. 20.5P Ch. 20 - Prob. 20.6P Ch. 20 - Prob. 20.7P Ch. 20 - Prob. 20.8P Ch. 20 - Prob. 20.9P Ch. 20 - Prob. 20.10P

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