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

Ram S. Mohan, Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas

Research output: Journal ArticleArticlepeer-review


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.
Original languageAmerican English
JournalJournal of Chemical Education
StatePublished - Jan 2000


  • Second-year undergraduate
  • organic chemistry
  • problem solving
  • decision making
  • mechanisms of reactions.


  • Organic Chemistry

Cite this