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Preparation of a d-Glucose-Derived Alkene. An E2 Reaction for the Undergraduate Organic Chemistry Laboratory

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Peter Norris and Andrew Fluxe

Department of Chemistry, Youngstown State University, Youngstown, OH 44555-3663

J. Chem. Educ., 2001, 78 (12), p 1676

DOI: 10.1021/ed078p1676

Publication Date (Web): December 1, 2001

Abstract

As the carbohydrates continue to gain attention for their central role in numerous areas of chemistry and biology, there is a growing need for experiments at the undergraduate level that highlight these fascinating compounds. In this article we describe a simple two-step laboratory experiment that may be used to highlight several important concepts introduced in sophomore organic chemistry, as applied to compounds of potential biological interest. The sequence begins with commercially available "diacetone glucose," which is converted to the highly crystalline tosylate derivative. Upon treatment of compound 2 with potassium tert-butoxide in THF solution, the alkene (3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose) is formed via an E2 reaction. The synthetic sequence allows for discussion of various concepts within organic chemistry, as well as for the application of analytical techniques such as polarimetry and one- and two-dimensional NMR.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Carbohydrates

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This article has been cited by 2 ACS Journal articles (2 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. ...
  Abstract | Hi-Res PDF | PDF w/ Links
Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside
Alexei V. Demchenko , Papapida Pornsuriyasak and Cristina De Meo
Journal of Chemical Education2006 83 (5), 782
- Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside
  Alexei V. Demchenko , Papapida Pornsuriyasak and Cristina De Meo
  Journal of Chemical Education2006 83 (5), 782
  A laboratory procedure for the synthesis of methyl 4,6-O-benzylidene-α-D-glucopyranoside is described. This compound is obtained in one synthetic step from commercially available methyl α-D-glucopyranoside. Purification of the target compound is achieved ...
  Abstract | Hi-Res PDF | PDF w/ Links