Download Centennial Honors College Western Illinois University Undergraduate Research Day 2012

Centennial Honors College
Western Illinois University
Undergraduate Research Day 2012
Poster Presentation
Development of a Convenient and Pedagogically Useful Green Oxidation Protocol
for Wider Adaptation in Undergraduate Laboratory Curriculum
Shanique Ries
Faculty Mentor: T. K. Vinod
Chemistry
Use of well-known reagents for the oxidation of different functional groups and the
mechanism of such transformations are an important part of any sophomore organic
chemistry 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) in presence of
Oxone as a stoichiometric oxidant is developed. Catalytic amount of commercially
available 2-iodobenzoic acid is used as the organoiodine precursor for IBX 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 and other hypervalent iodine
reagents as benign alternatives to commonly used and frequently discussed transition
metal based reagents.