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Acid-Catalyzed Isomerization of Carvone to Carvacrol

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Richard A. Kjonaas and Shawn P. Mattingly

Department of Chemistry, Indiana State University, Terre Haute, IN 47809

J. Chem. Educ., 2005, 82 (12), p 1813

DOI: 10.1021/ed082p1813

Publication Date (Web): December 1, 2005

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Aromatic Compounds

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