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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > September  >
In the Laboratory
Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate
Traci J. Speed, Jean P. McIntyre, and Dasan M. Thamattoor
Department of Chemistry, Colby College, Waterville, ME 04901
Cover
September 2004
Vol. 81 No. 9
p. 1355
Abstract
The synthesis of ethyl trans-cinnamate, by the reaction of benzaldehyde with the stabilized phosphorus ylid (carbethoxymethylene)triphenylphosphorane, serves as a useful experiment to illustrate the Wittig reaction in the introductory organic chemistry laboratory. The reaction is highly stereoselective and affords the product in excellent yield and purity. The stereochemistry of the product is established by examining the coupling constants displayed by the olefinic protons in the 1H NMR spectrum. The experiment highlights several important aspects of organic chemistry such as synthesis, stereochemistry, instrumental analysis, and molecular modeling.
Supplement
Instructions for the students, a list of chemicals and equipment, and the spectral and computational data are available.
*  Contents JCE2004p1355W.doc (Microsoft Word)
 
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More Information
*  Citation
 Speed, Traci J.; McIntyre, Jean P.; Thamattoor, Dasan M. J. Chem. Educ. 2004 81 1355.
*  Keywords
 Chromatography; Computational Chemistry; IR Spectroscopy; Laboratory Instruction; Mass Spectrometry; NMR Spectrometry; Organic Chemistry; Organic Synthesis; Stereochemistry
*  History
 Created:
Last Updated:		 July 28, 2004
August 13, 2004
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