The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed. Concept introduction: Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride. Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

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Answer 1

Question

Chapter 15, Problem 71P

Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

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Answer 2

Question

Chapter 15, Problem 71P

Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

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Answer 3

Question

Chapter 15, Problem 71P

Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

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Answer 4

Question

Chapter 15, Problem 71P

Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

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Answer 5

Chapter 15, Problem 71P

Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

Answer 6

Chapter 15, Problem 71P

Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

Answer 7

Chapter 15, Problem 71P

Interpretation Introduction

Interpretation:

The reaction mechanism for the formation of an anhydride from the reaction of butanedioic acid and thionyl chloride has to be proposed.

Concept introduction:

Dicarboxylic acid reacts with thionyl chloride and undergoes nucleophilic substitiution reaction at one carboxylic group to form acyl chloride.

Acyl chloride is the most reactive carboxylic derivative functional group and hence nucleophilic OH group of the second carboxylic group attacks the carbonyl of the acyl group. Chloride ion leaves as the leaving group and cyclic anhydride product from the dicarboxylic acid is formed.

Answer 8

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Answer 10

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Answer 11

Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3P Ch. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6P Ch. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...

Solution Summary: The author explains the reaction mechanism for the formation of an anhydride from butanedioic acid and thionyl chloride.

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Chapter 15 Solutions