Chapter F, Problem 1PP

Practice Problem F.1

Show how you might use a sulfur ylide to prepare

Interpretation Introduction

Interpretation:

The sulfur ylide required for the preparation of the given compounds is to be shown.

Concept introduction:

Sulphur ylide acts as the nucleophile and attacks the carbonyl carbon of aldehydes and ketones.

The intermediate formed in the reaction of sulphur ylide and carbonyl carbon is generally an epoxide rather than an alkene.

Answer to Problem 1PP

Solution:

The reactant used are:

The reactant used are:

Explanation of Solution

a)

In the formation of the given product, the ketone used is cyclo hexanone. In the first step, sulfur ylide acts as a nucleophile ( group of sulfur ylide) and attacks the carbonyl carbon of cyclo hexanone. After this, group is removed from the sulfur ylide, which results in the formation of the epoxy ring. The whole reaction can be shown as follows:

Hence, cyclohexane is used in combination with sulfur ylide to form the given compound.

b)

In the formation of the given product, the ketone used is acetone. In the first step, sulfur ylide acts as a nucleophile ( group of sulfur ylide) and attacks the carbonyl carbon of the acetone. After this, group is removed from the sulfur ylide which results in the formation of the epoxy ring.

The whole reaction can be shown as follows:

Hence, acetone is used in combination with sulfur ylide to form the given compound.