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Determination of the Regiochemistry of Disubstituted Arenes Generated by Addition of a Carbanion to the (η6-Anisole)Cr(CO)3 Complex

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Ashfaq A. Bengali , Cindy Samet and Samantha B. Charlton

Department of Chemistry, Dickinson College, Carlisle, PA 17013

J. Chem. Educ., 2001, 78 (1), p 68

DOI: 10.1021/ed078p68

Publication Date (Web): January 1, 2001

Section:

History, Education, and Documentation

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 (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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Aromatic Compounds

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Synthesis, Kinetics, and Thermodynamics: An Advanced Laboratory Investigation of the Cis-Trans Isomerization of Mo(CO)4(PR3)2
Kim E. Mooney , Ashfaq A. Bengali
Journal of Chemical Education2003 80 (9), 1044
- Synthesis, Kinetics, and Thermodynamics: An Advanced Laboratory Investigation of the Cis-Trans Isomerization of Mo(CO)4(PR3)2
  Kim E. Mooney , Ashfaq A. Bengali
  Journal of Chemical Education2003 80 (9), 1044
  An advanced laboratory experiment that requires students to thoroughly investigate the kinetics, thermodynamics, and the mechanism of the cis–trans isomerization of Mo(CO)4(PR3)2 (R = Et, n-butyl) is presented. The students synthesize the cis complex and ...
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