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  Home > JCE Print > Journal of Chemical Education > Issues > 1998  > November  >
In the Laboratory
Resolution of trans-Cyclohexane-1,2-diamine and Determination of the Enantiopurity Using Chiral Solid-Phase HPLC Techniques and Polarimetry
Patrick J. Walsh, Diane K. Smith, and Chris Castello
Department of Chemistry, San Diego State University, San Diego, CA 92182-1030
Cover
November 1998
Vol. 75 No. 11
p. 1459
Abstract
This experiment entails the resolution of trans-cyclohexane-1,2-diamine using either enantiomer of tartaric acid and the determination of the optical purity by HPLC and polarimetry. The experiment is designed to reinforce and broaden the students' understanding of the relationship between enantiomers and diasteriomers and of diasteriomeric interactions. Additionally, it illustrates the differences in physical properties (solubility and melting range) between a racemic mixture and the same compound in highly resolved form. The techniques employed herein for the determination of optical purity continue to be widely used in asymmetric synthesis and prove essential for the determination of the enantiomeric excess of a non-racemic mixture. The experiment also includes the synthesis of the bisamide of trans-cyclohexane-1,2-diamine.

See Letter re: this article.
More Information
*  Citation
 Walsh, Patrick J.; Smith, Diane K.; Castello, Chris. J. Chem. Educ. 1998 75 1459.
*  Keywords
 chromatography, analytical chem, organic chem, synthesis, separation science, stereochem
*  History
 Created:
Last Updated:		 June 18, 1999
June 24, 2005
Link to Letter added (April 2004).
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  Home > JCE Print > Journal of Chemical Education > Issues > 1998 > November > Page 1459


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