JCE Online Journal of Chemical Education
 | Subscriptions  | Software Orders  | Support  | Contributors  | Advertisers  | 

JCE Print
   Current Issue
 Previous Issues
 Supplements
 Search JCE Index

JCE Digital Library
   DigiDemos
 QBank
 SymMath
 WebWare

JCE Software
   Latest Releases
 Software & Video
 Downloads
 Support

Only@JCE Online
   JCE Online Store
 JCE HS CLIC
 JCE Discussion Forums
   Biographical Snapshots
 ChemEd Resource Shelf
 Featured Molecules
 Hal's Picks
 Project Chemlab
 Reviewed WWW Sites
 "Web-Ed" Articles

About JCE
   Features
 Publications
 Operations
 Outreach
 Contact Us


  Home > JCE Print > Journal of Chemical Education > Issues > 2001  > December  >
In the Laboratory
Preparation of a D-Glucose-Derived Alkene. An E2 Reaction for the Undergraduate Organic Chemistry Laboratory
Peter Norris and Andrew Fluxe
Department of Chemistry, Youngstown State University, Youngstown, OH 44555-3663
Cover
December 2001
Vol. 78 No. 12
p. 1676
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- a- 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.
Supplement
Detailed notes for the instructor are available.
*  Contents JCE2001p1676W.doc (Microsoft Word)
*  Download
JCE2001p1676W.pdf

JCE2001p1676W.zip

JCE2001p1676W.sit
More Information
*  Citation
 Norris, Peter; Fluxe, Andrew. J. Chem. Educ. 2001 78 1676.
*  Keywords
 Carbohydrates; Laboratory Instruction; NMR Spectrometry; Organic Chemistry; Organic Synthesis
*  History
 Created:
Last Updated:		 November 2, 2001
August 31, 2005
<< Previous Article Table of Contents Next Article >>
  Home > JCE Print > Journal of Chemical Education > Issues > 2001  > December  > Page 1676


Subscriptions
 Subscription Info
 Order Forms

JCE HS CLIC

Our Secondary School editors work hard to distill all the JCE materials to produce a fraction of particular interest to high school teachers. We call it CLIC.
 JCE HS CLIC

Contributions Welcome
JCE welcomes your submission
 Contributors' Corner

Advertisers
In recent years we have worked hard to better match our advertisers with our readers. When shopping for chemistry education materials, visit our advertisers' WWW sites first.
 Recent Advertisers

Be An Ambassador
Take JCE along on your outreach missions. Copies of the Journal, guest access to JCE Online, our publications catalog, and more are available for your participants.
 Outreach with JCE

Comments to
jceonline@chem.wisc.edu		 Copyright © Division of Chemical Education, Inc., American Chemical Society.
All rights reserved.