The Discovery-Oriented Approach to Organic Chemistry. 2. Selectivity in Alcohol Oxidation. An Exercise in ¹H NMR Spectroscopy for Sophomore Organic Laboratories

We have developed a simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine. 1H NMR analysis of the product mixture allows the student to determine the selectivity exhibited by the reagent.