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  Home > JCE Print > Journal of Chemical Education > Issues > 2003  > March  >
In the Laboratory
JCE WebWare
Featured Molecules: Enantiomers of Guaifenesin
William F. Coleman
Chemistry Department, Wellesley College, Wellesley, MA 02481

Randall J. Wildman
Department of Chemistry, University of Wisconsin–Madison, Madison, WI 53706

Cover
March 2003
Vol. 80 No. 3
p. 315
Full Text
The WebWare molecules of the month for March are the enantiomers of guaifenesin. The synthesis of the guaifenesin racemate and of the enantiomers is described in the paper by Stabile and Dicks, "Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets". Guaifenesin [3-(2-methoxyphenoxy)-1,2-propanediol] is used as an expectorant in a number of commercially available cough medicines.

Additional versions of this and other molecules are available at JCE WebWare.

Static image of (R)-(-)-guaifenesin molecule.

Figure 1. (R)-(-)-guaifenesin molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

 

 

Static image of aspirin molecule.

Figure 2. (S)-(+)-guaifenesin molecule. Interactive Chime-based structure (top); static structure graphic (bottom)
More Information
*  Citation
 Coleman, William F.; Wildman, Randall J. J. Chem. Educ. 2003 80 315.
*  Keywords
 General Chemistry; Internet / Web-Based Materials; Molecular Properties / Structure
*  History
 Created:
Last Updated:		 February 6, 2003
February 28, 2005
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