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The Discovery-Oriented Approach to Organic Chemistry. 3. Boron-trifluoride Catalyzed Rearrangement of cis- and trans-Stilbene Oxides. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories
Journal of Chemical Education (2000)
  • Ram S. Mohan, Illinois Wesleyan University
  • Erik A. Sgariglia
  • Regina Schopp
  • Kostas Gavardinas
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.

Keywords
  • Second-year undergraduate,
  • organic chemistry,
  • problem solving,
  • decision making,
  • mechanisms of reactions.
Disciplines
Publication Date
January, 2000
Citation Information
Ram S. Mohan, Erik A. Sgariglia, Regina Schopp and Kostas Gavardinas. "The Discovery-Oriented Approach to Organic Chemistry. 3. Boron-trifluoride Catalyzed Rearrangement of cis- and trans-Stilbene Oxides. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories" Journal of Chemical Education Vol. 77 Iss. 1 (2000)
Available at: http://works.bepress.com/ram_mohan/20/