ORGANIC CHEMISTRY-OWL V2 ACCESS
ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582422
Author: Brown
Publisher: CENGAGE L
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Chapter 28, Problem 28.7P
Interpretation Introduction

Interpretation:

The structural formulas for the enethiol forms of 6-mercaptopurine and 6-thioguanine has to be drawn.

Concept Introduction:

The functional group ketone (keto group) will be in equilibrium with the enol (alcohol group) form which is said to be the keto-enol tautomerization.  The keto form is more stable when compared to the enol form. The keto-enol conversion reaction is

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 28, Problem 28.7P , additional homework tip  1

Expert Solution & Answer
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Explanation of Solution

The enethiol is also the enol form which contains Sulphur molecule instead of Oxygen.  The enethiol form is the alcoholic form of the Sulphur.  The double bonded Sulphur is converted to thiol form of the Sulphur.

The enethiol form of 6-mercaptopurine is

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 28, Problem 28.7P , additional homework tip  2

The enethiol form of 6-thioguanine is

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 28, Problem 28.7P , additional homework tip  3

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