ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
12th Edition
ISBN: 9781119664635
Author: Solomons
Publisher: WILEY
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Chapter F, Problem 1PP

Practice Problem F.1

Show how you might use a sulfur ylide to prepare

Chapter F, Problem 1PP, Practice Problem F.1
Show how you might use a sulfur ylide to prepare

Expert Solution & Answer
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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:

ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  1

The reactant used are:

ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  2

Explanation of Solution

a)

ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  3

In the formation of the given product, the ketone used is cyclo hexanone. In the first step, sulfur ylide acts as a nucleophile (ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  4 group of sulfur ylide) and attacks the carbonyl carbon of cyclo hexanone. After this, ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  5 group is removed from the sulfur ylide, which results in the formation of the epoxy ring. The whole reaction can be shown as follows:

ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  6

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

b)

ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  7

In the formation of the given product, the ketone used is acetone. In the first step, sulfur ylide acts as a nucleophile (ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  8 group of sulfur ylide) and attacks the carbonyl carbon of the acetone. After this, ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  9 group is removed from the sulfur ylide which results in the formation of the epoxy ring.

The whole reaction can be shown as follows:

ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT, Chapter F, Problem 1PP , additional homework tip  10

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

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