A major component of my research program is the development of new "discovery" experiments for our organic chemistry courses. Many of the experiments currently performed by first and second year organic chemistry students were developed by my research group and published in the Journal of Chemical Education.

A project in its final stage of development allows students to discover rearrangements under E1 (dehydration) conditions and the possibility of an intramolecular Friedel-Crafts alkylation reaction.

 

There are still many topics covered in the course that do not have a discovery lab. Work in all of the following areas is still needed: enols and enolates; Markovnikov and anti- Markovnikov additions; 1,2 and 1,4 additions to dienes; E2; SN2 stereochemistry.

Certain techniques, such as Thin Layer Chromatography and Column Chromatography, are also absent from our introductory lab courses. I'd like to develop exercises to incorporate these common methods. An experiment that compares the behavior of enantiomers on standard and chiral TLC plates would be a useful activity when stereochemistry is being introduced.

 

Other research projects are of a more traditional nature. One project is the study of the equilibrium between conformations of trans-1,2-di-fluorocyclohexane as a function of solvent polarity (with low temperature ¹⁹F-NMR spectroscopy). Some solvent systems have been reported in the literature but we are expanding the study in order to better extrapolate the results to the gas phase. The study is being performed in collaboration with Professors Ken Wiberg (Yale University) and Kate Aubrecht (Holy Cross).

 

A new project under development is the synthesis of dinitroacridines. We will explore the possibility of producing one of the target compounds through the oxidation of Proflavin. The ability of these compounds to cause various mutations in the DNA of bacteria will be studied by Professor George Hoffmann (Holy Cross, Biology Department).