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  Home > JCE Print > Journal of Chemical Education > Issues > 2001  > January  >
In the Laboratory
Determination of the Regiochemistry of Disubstituted Arenes Generated by Addition of a Carbanion to the (h6-Anisole)Cr(CO)3 Complex
Ashfaq A. Bengali, Cindy Samet, and Samantha B. Charlton
Department of Chemistry, Dickinson College, Carlisle, PA 17013
Cover
January 2001
Vol. 78 No. 1
p. 68
Abstract
It has become increasingly important to demonstrate to undergraduates that chemistry is not many separate subfields, but rather a set of interconnected concepts. We describe a laboratory activity that integrates fundamental concepts of organic and organometallic chemistry and then employs standard instrumental techniques (GC) and molecular modeling to justify the results. Students synthesize the (h6-anisole)Cr(CO)3 complex and react it with the -:CH2CN anion to generate methoxyphenylacetonitrile. They then determine the relative amounts of the three possible regioisomers of the disubstituted arene using GC. We have shown this synthesis to be straightforward for students to accomplish, with results that are reproducible.
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Notes for the instructor and a handout for students are available.
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*  Citation
 Bengali, Ashfaq A.; Samet, Cindy; Charlton, Samantha B. J. Chem. Educ. 2001 78 68.
*  Keywords
 Aromaticity / Aromatics; Metal Carbonyls; Organic Synthesis; Organometallics; Laboratory Instruction
*  History
 Created:
Last Updated:		 November 30, 2000
August 31, 2005
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