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 > 1997  > January  >
In the Laboratory
The Wittig Reaction: Generation, Observation and Reactivity of a Phosphorous Ylide Intermediate. An Experiment for the Advanced Organic Chemistry Laboratory Course
Gary W. Breton
Berry College, Mount Berry, GA 30149
Cover
January 1997
Vol. 74 No. 1
p. 114
Abstract
An experiment has been devised that illustrates three important concepts in organic chemistry: the synthesis of an alkene via the Wittig reaction, characterization of a reactive intermediate by 1H NMR, and site - specific deuterium labelling. Deprotonation of ethyltriphenylphosphonium iodide (1) by methylsulfinyl carbanion (generated in situ by the reaction of NaH with DMSO-d6) results in the formation of the ylide, CH3CH-PPH3(2 -H). An ensuing, rapid deuterium exchange process between the deuterated solvent, and 2-H at the C-1 position affords CH3CD - PPH3 (2-D). The 1H NMR spectrum of 2-D was obtained, and the ylide was quenched with benzophenone to obtain 2-deutero-diphenylpropene (3) in 42% yield.
More Information
*  Citation
 Breton, Gary W. J. Chem. Educ. 1997 74 114.
*  Keywords
*  History
 Created:
Last Updated:		 July 29, 1999
June 23, 2005
<< Previous Article Table of Contents Next Article >>
  Home > JCE Print > Journal of Chemical Education > Issues > 1997 > January > Page 114


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.