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Use of 1H NMR in Assigning Carbohydrate Configuration in the Organic Laboratory

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John L. Sorensen , Ross Witherell and Lois M. Browne

Department of Chemistry, University of Alberta, Edmonton, AB Canada T6G 2G2

J. Chem. Educ., 2006, 83 (5), p 785

DOI: 10.1021/ed083p785

Publication Date (Web): May 1, 2006

Section:

History, Education, and Documentation

Abstract

This article describes a laboratory experiment suitable for an advanced undergraduate organic laboratory class that combines synthetic organic chemistry and ¹H NMR in the determination of the identity of a simple carbohydrate. The focus of the laboratory course is the application of modern organic techniques and training in the use of high-resolution NMR in the undergraduate organic laboratory. The experiment described herein combines the cumulative knowledge of both lab technique and NMR sample preparation with data processing. Students are asked to acetylate an unknown methyl glycoside, to purify the product of the reaction by column chromatography, and to prepare and submit a sample for ¹H NMR spectroscopy. Each student is required to process the raw FID data to determine the identity of their unknown sugar. The experiment demonstrates the use of the coupling constant in the determination of an unknown structure.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Carbohydrates

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Stereochemical Control in Carbohydrate Chemistry
Emma M. Dangerfield and Bridget L. Stocker , Rhys Batchelor , Peter T. Northcote and Joanne E. Harvey
Journal of Chemical Education2008 85 (5), 689
- Stereochemical Control in Carbohydrate Chemistry
  Emma M. Dangerfield and Bridget L. Stocker , Rhys Batchelor , Peter T. Northcote and Joanne E. Harvey
  Journal of Chemical Education2008 85 (5), 689
  Carbohydrates, in the form of glycoconjugates, have recently been shown to control a wide range of cellular processes. Accordingly, students interested in the study of organic chemistry and biomedical sciences should be exposed to carbohydrate chemistry. ...
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