Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 24, Problem 24.13P
Interpretation Introduction

Interpretation:

The percentages of α- and β-D- glucopyranose present at equilibrium is to be calculated. The corresponding values are to be compared with the given data.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also known as asymmetric or stereogenic centers. A chiral molecule is an optically active molecule. The observed optical rotation of a compound is given by the expression as shown below.

α=[α]cl

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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.
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