ORGANIC CHEMISTRY-ACCESS
ORGANIC CHEMISTRY-ACCESS
6th Edition
ISBN: 9781260475586
Author: SMITH
Publisher: MCG
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Chapter 26, Problem 64P
Interpretation Introduction

Interpretation: The D-aldopentose which on oxidation produces optically active aldaric acid and that undergoes Wohl Degradation to yield D-aldotetrose which on oxidation produces optically active aldaric acid is to be predicted.

Concept introduction: Carbohydrates containing aldehydes are known as aldoses. Wohl Degradation is a method of shortening the aldose by one carbon atom by cleavage of C1C2 bond.

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Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a D-aldotetrose that is oxidized to an optically active aldaric acid?
A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two D-aldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A–C?
A D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?

Chapter 26 Solutions

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