(a) Interpretation: The product of the given reaction is to be predicted and a detailed mechanism is to be provided. Concept introduction: Diazomethane is used as an alkylating agent specific to carboxylic acids. Since one of it resonance structures has a negative charge on the less electronegative carbon atom, it acts a base. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

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Answer 1

Question

Chapter 10, Problem 10.14P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. Since one of it resonance structures has a negative charge on the less electronegative carbon atom, it acts a base. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. It is a base, as one of its resonance structures has a negative charge on the less electronegative carbon atom. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

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The reaction shown here is an example of the Favorskii reaction, which involves an R¯ leaving group in a nucleophilic addition-elimination reaction. (a) Draw the complete, detailed mechanism for this reaction and explain why R can act as a leaving NaOH H2O group. (b) Suggest how you can synthesize an ester from cyclopropanone using only this reaction.

(a) Predict the product of the set of reactions shown here. (b) Draw the complete, detailed mechanism for the formation of the synthetic intermediate that is not shown.

(SYN) Show how each of the following compounds can be synthesized from an acid chloride and either water, an alcohol, or an amine. For each reaction, provide the complete, detailed mechanism.

Answer 2

Question

Chapter 10, Problem 10.14P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. Since one of it resonance structures has a negative charge on the less electronegative carbon atom, it acts a base. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. It is a base, as one of its resonance structures has a negative charge on the less electronegative carbon atom. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

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Answer 3

Question

Chapter 10, Problem 10.14P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. Since one of it resonance structures has a negative charge on the less electronegative carbon atom, it acts a base. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. It is a base, as one of its resonance structures has a negative charge on the less electronegative carbon atom. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

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Answer 4

Question

Chapter 10, Problem 10.14P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. Since one of it resonance structures has a negative charge on the less electronegative carbon atom, it acts a base. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. It is a base, as one of its resonance structures has a negative charge on the less electronegative carbon atom. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

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Answer 5

Chapter 10, Problem 10.14P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. Since one of it resonance structures has a negative charge on the less electronegative carbon atom, it acts a base. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. It is a base, as one of its resonance structures has a negative charge on the less electronegative carbon atom. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Answer 6

Chapter 10, Problem 10.14P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. Since one of it resonance structures has a negative charge on the less electronegative carbon atom, it acts a base. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Answer 7

Chapter 10, Problem 10.14P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. Since one of it resonance structures has a negative charge on the less electronegative carbon atom, it acts a base. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. It is a base, as one of its resonance structures has a negative charge on the less electronegative carbon atom. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted and a detailed mechanism is to be provided.

Concept introduction:

Diazomethane is used as an alkylating agent specific to carboxylic acids. It is a base, as one of its resonance structures has a negative charge on the less electronegative carbon atom. It is a sufficiently strong base to deprotonate carboxylic acids. The carboxylate anion produced is a nucleophile and immediately reacts with the methyl diazonium cation formed in the first step to produce a methyl ester.

Answer 10

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Answer 11

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Answer 13

Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

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