The Discovery-Oriented Approach to Organic Chemistry. 4. Epoxidation of p-Methoxy-trans-β-methylstyrene. An Exercise in 1H NMR and 13C NMR Spectroscopy for Sophomore Organic Laboratories

Ram S. Mohan, Rebecca S. Centko

Research output: Journal ArticleArticlepeer-review

Abstract

Epoxidation of alkenes using peroxyacids is one of the most fundamental reactions in organic chemistry, yet there are very few examples of laboratory experiments that illustrate this important reaction. We have developed a discovery-oriented lab experiment that illustrates epoxidation of alkenes as well as the reactivity of epoxides toward acids. The experiment involves reaction of p-methoxy-trans-β-methylstyrene (trans-anethole) with m-chloroperoxybenzoic acid (MCPBA), in both the absence and presence of a buffer, followed by product identification using 1H NMR, 13C NMR, and IR spectroscopy. The added element of discovery ensures that students' interest and enthusiasm are retained.
Original languageAmerican English
JournalJournal of Chemical Education
Volume78
StatePublished - Jan 2001

Keywords

  • Second-year undergraduate
  • organic chemistry
  • inquiry-based discovery learning
  • IR spectroscopy.

Disciplines

  • Organic Chemistry

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