Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 24, Problem 24.28P
Interpretation Introduction

Interpretation:

The structure of aldehexose A which on reaction with nitric acid gives aldaric acid is to be identified

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate which consists of six carbon atoms chain and an aldehyde group is known as aldohexose.

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How many asymmetric carbons and stereoisomers are there for an aldohexose? For aketohexose?
An important technique for establishing relative configurations among isomeric aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.
How many chiral centers are in B-d-glucopyranose and a-D-galactopyranose? How many stereoisomers of these two aldohexoses can theoretically be drawn?
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