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.
Mohan, Ram and Shadwick, Steven, "The Discovery-Oriented Approach to Organic Chemistry. 2. Selectivity in Alcohol Oxidation. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories" (1999). Scholarship. 55.