JCE Online Journal of Chemical EducationDivision of Chemical Education, American Chemical SocietyAmerican Chemical Society
 | Subscriptions  | Software Orders  | Support  | Contributors  | Advertisers  | 

JCE Print

JCE Digital Library

JCE Software

Only@JCE Online

About JCE


  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > January  >
In the Laboratory
Green Chemistry
Greening Wittig Reactions: Solvent-Free Synthesis of Ethyl trans-Cinnamate and trans-3-(9-Anthryl)-2-Propenoic Acid Ethyl Ester
Kim Chi Nguyen and Haim Weizman
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0303
Cover
January 2007
Vol. 84 No. 1
p. 119

Abstract
The two reactions presented here are solvent-free alternatives to published procedures of Wittig reactions. The first example is a reaction between a solid phosphorane and liquid aldehyde while the second reaction takes place in a melt. Both reactions are fast, proceed with high yield and excellent stereoselectivity, and their product isolation is simple. The simplicity of the experiments allows students to perform them simultaneously and to construct a small NMR data set. The spectral data provide a basis for an inquiry-based discussion of (i) the factors influencing the chemical shifts of alkenyl proton, (ii) the analysis of NMR spectrum containing a mixture, and (iii) the role of strong dipole–dipole interactions in dictating the stereochemical outcome of the Wittig reaction.

See JCE Featured Molecules.

Supplement
List of chemicals and equipment, student handout, notes for the instructor, NMR spectra, and computational data are available.
*
Download
Contents
More Information
*
Citation
Nguyen, Kim Chi; Weizman, Haim. J. Chem. Educ. 2007, 84, 119.
*
Keywords
Aldehydes / Ketones; Alkenes; Green Chemistry; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; NMR Spectroscopy; Organic Chemistry; Upper-Division Undergraduate
*
History
Created:
Last Updated:
12/5/2006
3/20/2007
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > January  > Page 119


Subscriptions

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.


Contributions Welcome
JCE welcomes your submission

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.

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.