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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > January  >
In the Laboratory
The Discovery-Oriented Approach to Organic Chemistry. 3. Rearrangement of cis- and trans-Stilbene Oxides with Boron Trifluoride Etherate. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories
Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas, and Ram S. Mohan
Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61701
Cover
January 2000
Vol. 77 No. 1
p. 79
Abstract
Epoxides, or oxiranes, are among the most versatile intermediates in organic synthesis. Yet very few examples of laboratory experiments involving reactions of epoxides are to be found in lab texts. We have developed a discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate. The identity of the product can be easily determined by 1H NMR spectroscopy and, in case of the trans isomer, by preparation of the semicarbazone derivative as well. In spite of the simplicity of the experiment, the element of discovery ensures that student interest and enthusiasm are retained.
Supplement
Notes to the instructor and a suggested discovery-oriented methodology are provided.
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*  Citation
 Sgariglia, Erik A.; Schopp, Regina; Gavardinas, Kostas; Mohan, Ram S. J. Chem. Educ. 2000 77 79.
*  Keywords
 Organic Chemistry; Problem-Based Learning; Mechanisms; NMR Spectrometry; Laboratory Instruction
*  History
 Created:
Last Updated:		 December 9, 1999
August 31, 2005
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