Bengali, Ashfaq A., Cindy Samet, and Samantha B. Charlton. Determination of the Regiochemistry of Disubstituted Arenes Generated by Addition of a Carbanion to the (η6-Anisole)Cr(CO)3 Complex. Journal of Chemical Education 78, no. 1 (2001): 68-70.

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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 (η6-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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