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.