Green Oxidation of Menthol Enantiomers and Analysis by Circular Dichroism Spectroscopy: An Advanced Organic Chemistry Laboratory

Green chemistry addresses environmental concerns associated with chemical processes and increases awareness of possible harmful effects of chemical reagents. Efficient reactions that eliminate or reduce the use of organic solvents or toxic reagents are increasingly available. A two-week experiment is reported that entails the calcium hypochlorite oxidation of menthol to menthone. The experiment enhances student interest, knowledge, and techniques in organic chemistry, while promoting the development of socially responsible citizens. The experiment is suitable for an advanced organic chemistry laboratory. The first objective of this experiment is to perform an oxidation reaction that uses environmentally friendly, nonhazardous, and cost-effective reactants. A second objective is to introduce circular dichroism spectroscopy, a powerful analytical technique typically overlooked in the undergraduate curriculum. The students also gain experience in IR and NMR spectroscopies.