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  Home > JCE Print > Journal of Chemical Education > Issues > 2005  > December  >
In the Laboratory
Acid-Catalyzed Isomerization of Carvone to Carvacrol
Richard A. Kjonaas and Shawn P. Mattingly
Department of Chemistry, Indiana State University, Terre Haute, IN 47809
Cover
December 2005
Vol. 82 No. 12
p. 1813
Abstract
The acid-catalyzed isomerization of carvone (oil of spearmint) to carvacrol (oil of origanum) in the sophomore organic chemistry laboratory is discussed. The experiment demonstrates several important concepts including (i) formation of a carbocation by protonation of an alkene, (ii) rearrangement of a carbocation, (iii) deprotonation of a carbocation, (iv) acid-catalyzed enolization, and (v) aromaticity. The experiment is especially suitable for use with low-field permanent-magnet FT–NMR for two important reasons: (i) even the 60 MHz proton spectrum is interpretable by the students and (ii) the product is a liquid that is obtained from an inexpensive starting material in sufficiently high yield and purity so that a neat or highly concentrated NMR sample can be prepared for 13C NMR analysis.
Supplement
The students' procedure, instructor's notes, and spectra of the product are available.
*  Contents JCE2005p1813W.doc (Microsoft Word)
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*  Citation
 Kjonaas, Richard A.; Mattingly, Shawn P. J. Chem. Educ. 2005 82 1813.
*  Keywords
 Aromatic Compounds; Hands-On Learning / Manipulatives; Laboratory Instruction; Medicinal Chemistry; Natural Products; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate
*  History
 Created:
Last Updated:		 October 25, 2005
November 4, 2005
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