Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds.  It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds.  It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds.  It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.