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An Engaging Illustration of the Physical Differences among Menthol Stereoisomers

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Edward M. Treadwell and T. Howard Black

Department of Chemistry, Eastern Illinois University, Charleston, IL 61920

J. Chem. Educ., 2005, 82 (7), p 1046

DOI: 10.1021/ed082p1046

Publication Date (Web): July 1, 2005

Section:

History, Education, and Documentation

Abstract

The differences and similarities in the physical behavior of enantiomers and diastereomers can easily be demonstrated using the commercial stereoisomers (?)-menthol, (+)-menthol, (+)-isomenthol, and (+)-neomenthol. Thin-layer chromatography and melting point determinations clearly show that diastereomers have different physical properties from enantiomers and each other, but that enantiomers have identical physical properties in achiral environments. By obtaining a mixed melting point and optical rotations the difference in enantiomers can be observed. The exercise serves to reinforce the consequences of stereochemistry in terms of physical properties, as well as relating the differences in structure that lead to different types of stereoisomers. An attention-getting demonstration, suitable for the classroom or laboratory, of the melting point depression of a mixture of two enantiomers is also featured.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Chirality / Optical Activity

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Received: August 03, 2009

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An Engaging Illustration of the Physical Differences among Menthol Stereoisomers