The Discovery-Oriented Approach to Organic Chemistry. 4. Epoxidation of p-Methoxy-trans-β[beta]-methylstyrene: An Exercise in NMR and IR Spectroscopy for Sophomore Organic Laboratories

• Rebecca S. Centko ^[1] ; Ram S. Mohan ^[1]
  1. [1] Illinois Wesleyan University

     Illinois Wesleyan University

     Township of Bloomington City, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 78, Nº 1, 2001, pág. 77
• Idioma: inglés
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• Resumen

  • 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.