a) Ethyl pentanoate Interpretation: Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated. Concept introduction: Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides . The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl. To state: Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Question

What are the missing intermediates 1, 2, and 3? Please include a detailed explanation explaining the steps of malonic ester synthesis. Please include drawings of the intermediates and how they occur.

Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.SE, Problem 43AP

Interpretation Introduction

a) Ethyl pentanoate

Interpretation:

Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

b) Ethyl 3-methylbutanoate

Interpretation:

Whether ethyl 3-methylbutaonate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 3-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

c) Ethyl 2-methylbutanoate

Interpretation:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

d) Ethyl 2,2-dimethylpropanoate

Interpretation:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

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Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.SE, Problem 43AP

Interpretation Introduction

a) Ethyl pentanoate

Interpretation:

Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

b) Ethyl 3-methylbutanoate

Interpretation:

Whether ethyl 3-methylbutaonate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 3-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

c) Ethyl 2-methylbutanoate

Interpretation:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

d) Ethyl 2,2-dimethylpropanoate

Interpretation:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Expert Solution & Answer

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.SE, Problem 43AP

Interpretation Introduction

a) Ethyl pentanoate

Interpretation:

Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

b) Ethyl 3-methylbutanoate

Interpretation:

Whether ethyl 3-methylbutaonate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 3-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

c) Ethyl 2-methylbutanoate

Interpretation:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

d) Ethyl 2,2-dimethylpropanoate

Interpretation:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Expert Solution & Answer

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.SE, Problem 43AP

Interpretation Introduction

a) Ethyl pentanoate

Interpretation:

Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

b) Ethyl 3-methylbutanoate

Interpretation:

Whether ethyl 3-methylbutaonate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 3-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

c) Ethyl 2-methylbutanoate

Interpretation:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

d) Ethyl 2,2-dimethylpropanoate

Interpretation:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Expert Solution & Answer

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Answer 5

Chapter 22.SE, Problem 43AP

Interpretation Introduction

a) Ethyl pentanoate

Interpretation:

Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

b) Ethyl 3-methylbutanoate

Interpretation:

Whether ethyl 3-methylbutaonate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 3-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

c) Ethyl 2-methylbutanoate

Interpretation:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Interpretation Introduction

d) Ethyl 2,2-dimethylpropanoate

Interpretation:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 6

Chapter 22.SE, Problem 43AP

Interpretation Introduction

a) Ethyl pentanoate

Interpretation:

Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 7

Chapter 22.SE, Problem 43AP

Interpretation Introduction

a) Ethyl pentanoate

Interpretation:

Whether ethyl pentanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl pentanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 8

Interpretation Introduction

b) Ethyl 3-methylbutanoate

Interpretation:

Whether ethyl 3-methylbutaonate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 3-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 9

Interpretation Introduction

b) Ethyl 3-methylbutanoate

Interpretation:

Whether ethyl 3-methylbutaonate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 3-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 10

Interpretation Introduction

c) Ethyl 2-methylbutanoate

Interpretation:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 11

Interpretation Introduction

c) Ethyl 2-methylbutanoate

Interpretation:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2-methylbutanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 12

Interpretation Introduction

d) Ethyl 2,2-dimethylpropanoate

Interpretation:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 13

Interpretation Introduction

d) Ethyl 2,2-dimethylpropanoate

Interpretation:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis is to be stated. If so the alkyl halide to be used is to be stated.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids from alkyl halides. The ester is converted into its enolate ion which then attacks the alkyl halide. Hydrolysis and decarboxylation of the alkylated product yield the carboxylic acid which has two carbon extra than the alkyl halide. The acid can then be converted into ester by treating with ethanol in the presence of HCl.

To state:

Whether ethyl 2,2-dimethylpropanoate can be prepared by malonic ester synthesis and to indicate the alkyl halide to be used.

Answer 14

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Answer 15

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Ch. 22.1 - Prob. 1P Ch. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3P Ch. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5P Ch. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7P Ch. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P

Chapter 22 Solutions