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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > October  >
In the Laboratory
Green Chemistry
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment
Sam H. Leung and Stephen A. Angel
Department of Chemistry, Washburn University, Topeka, KS 66621
Cover
October 2004
Vol. 81 No. 10
p. 1492
Abstract
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry. This experiment can be extended to include 1H NMR analysis of the products. Students can observe the difference in the coupling constants of the alkenyl protons between the E and Z isomers of 1-(4-bromophenyl)-2-phenylethene.
Supplement
Instructions for the students and notes for the instructor are available.
*  Contents JCE2004p1492W.doc (Microsoft Word)
 
*  Download



 
More Information
*  Citation
 Leung, Sam H.; Angel, Stephen A. J. Chem. Educ. 2004 81 1492.
*  Keywords
 Chromatography; Green Chemistry; Laboratory Instruction; Microscale; NMR Spectrometry; Organic Chemistry; Organic Synthesis
*  History
 Created:
Last Updated:		 August 31, 2004
September 8, 2004
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