The free radical halogenation of alkanes experiment is found in many organic chemistry laboratory curriculums because it can be used to introduce important physical organic chemistry concepts, advanced instrumentation, and opportunities for collaborative approaches that can engage students in the process of using their own data to answer questions. We describe an approach that uses 1H NMR spectroscopy to quantify the products resulting from the mono-chlorination of a structurally diverse group of substrates. Through data sharing and the use of characteristic chemical shift data for each product, organic chemistry students calculate relative reactivity values for all of the substrates. Advanced students are not provided with chemical shift data, and instead take a series of 1D 1H TOCSY NMR experiments to elucidate the structure of each product before continuing on to determine relative reactivity values. In both cases, students use their relative reactivity data to develop an understanding of the important role that substitution and functionality play in radical reactivity.

Free radical chlorination of alkanes: Application of 1H NMR and 1D TOCSY NMR spectroscopy to the analysis of reaction products

251st National Meeting (2016)

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