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ERIC Number: EJ820288
Record Type: Journal
Publication Date: 2006-Jul
Pages: 4
Abstractor: As Provided
Reference Count: 24
ISSN: ISSN-0021-9584
Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions
Mak, Kendrew K. W.; Lai, Y. M.; Siu, Yuk-Hong
Journal of Chemical Education, v83 n7 p1058-1061 Jul 2006
This article describes a discovery-oriented experiment for demonstrating the selectivity of two epoxidation reactions. Peroxy acids and alkaline H[subscript 2]O[subscript 2] are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich alkenes while the latter works better with alpha,beta-unsaturated carbonyl compounds. The selectivity of these two reagents on carvone, a naturally occurring compound that contains both types of C=C bonds, was investigated. The product mixtures obtained from the two different reactions were analyzed by thin-layer chromatography and [superscript 1]H NMR spectroscopy. Both of the reactions were found to be regiospecific. The selectivity was attributed to the roles played by the alkene C=C bonds, which act as a nucleophile in the peroxy acid epoxidation but as an electrophile in the alkaline H[subscript 2]O[subscript 2] reaction. The discovery-oriented approach is aimed at strengthening students' knowledge of the relationship between the reaction selectivity and the mechanisms. (Contains 5 schemes, 5 figures, and 4 notes.)
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A