Nitration is one of the most fundamental reactions in organic chemistry. However, the majority of the nitration experiments found in the standard lab textbooks are of the "cookbook" variety and convey none of the excitement associated with discovery in experimental chemistry. We have developed two simple nitration experiments that present the student with a puzzle and are a good exercise in 1H NMR and 13C NMR spectroscopy. 13 C NMR spectroscopy is a powerful structure elucidation tool and yet not many examples of the use of 13C NMR spectroscopy in organic lab experiments can be found. The experiment involves nitration of unknown organic compounds and product analysis by 1H NMR and 13C NMR spectroscopy, which enables the student to determine the identity of the unknown. In spite of the simplicity of the experiment, the element of discovery ensures that student interest and enthusiasm are retained.
Mohan, Ram; McElveen, Sonia; Gavardinas, Kostas; and Stamberger, Jean, "The Discovery-Oriented Approach to Organic Chemistry 1. Nitration of Unknown Organic Compounds. An Exercise in 1H NMR and 13C NMR Spectroscopy for Sophomore Organic Laboratories" (1999). Scholarship. 40.