CNCT ORG CHEM 6 2020
CNCT ORG CHEM 6 2020
6th Edition
ISBN: 9781266807244
Author: SMITH
Publisher: MCG
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Chapter 26.10, Problem 26P
Interpretation Introduction

Interpretation: The structures for compound A and B are to be predicted.

Concept introduction: Wohl degradation is a method which is used for the contraction of the carbon chains in aldose. In this method, the aldose chain shortens by the cleavage of C1-C2 bond.

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A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two Daldohexoses, 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?
Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a Daldotetrose that is oxidized to an optically active aldaric acid?
A D-aldohexose A is formed from an aldopentose B by the Kiliani-Fischer synthesis. Reduction of A with NABH4 forms an optically inactive alditol. Oxidation of B forms an optically active aldaric acid. What are the structures of A and B?

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CNCT ORG CHEM 6 2020

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