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  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > December  >
In the Laboratory
Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction
Eric Martin and Cynthia Kellen-Yuen
Department of Chemistry , California State University–Sacramento, Sacramento, CA 95819-6057
Cover
December 2007
Vol. 84 No. 12
p. 2004

Abstract
A greener, microwave-assisted Wittig reaction has been developed for the second-semester organic teaching laboratory. Utilizing this microwave technique, a variety of styrene derivatives have been successfully synthesized from aromatic aldehydes in good yields (41–68%). The reaction not only occurs under neat reaction conditions, but also employs an inexpensive, non-pyrophoric base and readily available glassware. The average reaction times have been reduced to a matter of minutes rather than the hours typical of literature procedures. This method will therefore provide a quick and easy example of a Wittig reaction that can be accomplished in any undergraduate organic lab. The mixture of cis and trans alkenes produced by this method also provides instructors with opportunities to emphasize spectroscopic analysis of product mixtures.
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Instructions for the students, notes for the instructor, and 1H NMR and GC–MS spectra are available.
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Citation
Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ. 2007, 84, 2004.
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Keywords
Aldehydes / Ketones; Alkenes; Chromatography; Green Chemistry; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; Mass Spectrometry; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Spectroscopy; Synthesis
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History
Created:
Last Updated:
10/25/2007
10/31/2007
 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.
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