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The alkylation of aromatic compounds is a very important industrial process. Typically these alkylations are performed using strong Lewis acids like aluminum trichloride as catalysts. However the use of these catalysts often requires an aqueous work-up to remove the aluminum and also leads to mixtures of products due to carbocation rearrangement.
By using graphite this greener alkylation eliminates unwanted side products and transforms the work-up to a simple filtration of the catalyst. Also notable, this green alternative uses safer and cheaper reagents than typical alkylations.
Possible teaching topics surrounding this experiment include principles of green chemistry, electrophilic aromatic chemistry, Friedel-Crafts alkylations, catalysis, thin-layer chromatography, proton NMR and 2D NMR such as COSY.
Supplemental information includes lab equipment and chemical lists, lab procedure, student lab report form, and instructor tips.
Summary prepared September 2008 by Douglas M. Young at the University of Oregon.
Sereda, G. A.; Rajpara, V. B. J. Chem. Educ., Print 2007, 84, pp 692-693.