Relatively few experiments for the introductory organic chemistry laboratory demonstrate the utility of metal-catalyzed reactions in organic chemistry. A copper-catalyzed aerobic oxidative dimerization of 1-methylimidazole is described that introduces this topic. The reaction uses a low-cost substrate, a low-cost precatalyst that is stable to air and moisture, and a readily prepared base. The experiment can be performed using equipment found in a typical organic teaching lab. The crude product can be analyzed by 1H NMR spectroscopy. The experiment allows for a general discussion of redox processes of organic substrates and green chemistry.
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