Chapter 19.6, Problem 19.10P

(a)

Interpretation Introduction

Interpretation:

The synthesis of acetoacetic ester can be used to prepare 5-phenyl-2,5-pentanedione has to be showed.

Concept Introduction:

Acetoacetic 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 synthesis of acetoacetic ester can be used to prepare 1-cyclopentyl-1-ethanone has to be showed.

Concept Introduction:

Acetoacetic 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 synthesis of acetoacetic ester can be used to prepare 3-ethyl-2-pentanone has to be showed.

Concept Introduction:

Acetoacetic 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.