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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
Journal of Chemical Education (2001)
  • Ram S. Mohan, Illinois Wesleyan University
  • Rebecca S. Centko
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.

Keywords
  • Second-year undergraduate,
  • organic chemistry,
  • inquiry-based discovery learning,
  • IR spectroscopy.
Disciplines
Publication Date
January, 2001
Citation Information
Ram S. Mohan and Rebecca S. Centko. "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" Journal of Chemical Education Vol. 78 Iss. 1 (2001)
Available at: http://works.bepress.com/ram_mohan/17/