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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > December  >
In the Classroom
Chemical Principles Revisited
Precision in Stereochemical Terminology
LeRoy G. Wade, Jr.
Department of Chemistry, Whitman College, Walla Walla, WA 99362
Cover
December 2006
Vol. 83 No. 12
p. 1793

Abstract
Many organic chemists have begun to use the Mislow term stereocenter (or stereogenic atom) as an alternative to the traditional term asymmetric carbon atom and the slightly broader IUPAC term chirality center. But the term stereocenter is defined much more broadly. It includes a wide variety of structures that are neither chirality centers nor asymmetric carbon atoms. The rules that students learn about asymmetric carbon atoms are no longer true when one substitutes the broader term stereocenter. Asymmetric carbon atoms are defined structurally, and students can easily find them to use as a tool to help in understanding the stereochemistry and finding the stereoisomers. In contrast, students must already know which stereoisomers exist to identify the stereocenters. This article recommends that instructors use the precise terms asymmetric carbon atom and chirality center when they apply, and use the broader term stereocenter only when there is a need to include stereogenic atoms that are not chirality centers.
More Information
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Citation
Wade, LeRoy G., Jr. J. Chem. Educ. 2006 83 1793.
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Keywords
Chirality / Optical Activity; Diastereomers; Enantiomers; Misconceptions / Discrepant Events; Organic Chemistry; Second-Year Undergraduate; Stereochemistry
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History
Created:
Last Updated:
10/30/2006
10/31/2006
  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > December  > Page 1793


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