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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 16 (2011) pp 304-306

Determination of Relative Stereochemistry of an Unknown Carbohydrate: Application of Two-dimensional NMR and the Karplus Relationship

Jonathan S. Rhoad

Department of Chemistry, Missouri Western State University, 4525 Downs Drive, St. Joseph, MO 64507,
Received July 5, 2011. Accepted September 19, 2011.

Published: 21 November 2011

Abstract. An experiment designed for the second semester organic chemistry course is described. An unknown carbohydrate is derivatized and recrystallized to give a single diastereomer. The absolute assignment of all hydrogen peaks can be made based on the correlation spectroscopy (COSY) spectrum, and the relative stereochemistry can be assigned based on the 3JHH coupling constants according to the Karplus relationship.

Key Words: Laboratories and Demonstrations; organic chemistry; nuclear magnetic resonance; pyranoside stereochemistry

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Article in PDF format (132 KB) HTML format

Supporting Materials:

The 1D 1H and 13C spectra for the derivatives are included (222 KB)

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