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

Authors

Ram Mohan, Illinois Wesleyan UniversityFollow
Rebecca Centko

Publication Date

January 2001

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.

Disciplines

Organic Chemistry

Recommended Citation

Mohan, Ram and Centko, Rebecca, "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" (2001). Scholarship. 29.
https://digitalcommons.iwu.edu/chem_scholarship/29