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Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment

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Sam H. Leung and Stephen A. Angel

Department of Chemistry, Washburn University, Topeka, KS 66621

J. Chem. Educ., 2004, 81 (10), p 1492

DOI: 10.1021/ed081p1492

Publication Date (Web): October 1, 2004

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.

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Received: August 03, 2009

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Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment