Development of Two Green Chemistry Laboratory Experiments for an Undergraduate Curriculum

Most, if not all, of the traditional oxidizing agents covered in an undergraduate lecture course are transition metal based reagents which are toxic and are also potential environmental pollutants. While the ease and efficiency (% yield) of the oxidation reactions using these reagents are highlighted during the lecture class, the deleterious health and environmental aspects of these reagents are often ignored or omitted in classroom discussions. A green oxidation procedure for oxidation of alcohols using catalytic amounts of in-situ generated o-iodoxybenzoic acid (IBX 48) in presence of Oxone as a stoichiometric oxidant is developed. Catalytic amount of commercially available 2-iodobenzoic acid 42 is used as the organoiodine precursor for IBX 48 in the reaction.;This convenient procedure for the oxidation of alcohols, completed in a 2.5 h laboratory period, is carried out in aqueous solvent mixtures. Students are introduced to several pedagogically relevant green chemistry principles including the use of aqueous reaction medium, non-extractive product isolation procedure, and use of benign and catalytic reagents through this convenient oxidation experiment. Finally, this experiment also allow instructors to discuss the use of IBX 48and other hypervalent iodine reagents as benign alternatives to commonly used and frequently discussed transition metal based reagents.