The product of the claisen condensation of ethyl phenylacetate in the presence of sodium ethoxide ion has to be shown. Concept introduction: When two molecules of an ester undergo condensation, then it is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile. A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base. The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.

Question

Etoposide, sold as a phosphate derivative with the trade name of Etopophos, is used for the treatment of lung cancer, testicular cancer, and lymphomas. (a) Locate the acetals in etoposide. (b) What products are formed when all of the acetals are hydrolyzed with aqueous acid?

Answer 1

Question

Chapter 19, Problem 19.29P

(a)

Interpretation Introduction

Interpretation:

The product of the claisen condensation of ethyl phenylacetate in the presence of sodium ethoxide ion has to be shown.

Concept introduction:

When two molecules of an ester undergo condensation, then it is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.

A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.

The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.

(b)

Interpretation Introduction

Interpretation:

The product of the claisen condensation of methyl hexanoate in the preesnce of sodium ethoxide ion has to be shown.

Concept introduction:

When two molecules of an ester undergo condensation, then it is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.

A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.

The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.

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