The focus of this research entails the synthesis and investigation of the chemistry of an array of highly fluorinated target molecules, all of which have skeletons of twelve or fewer carbon atoms. Ab initio quantum mechanical calculations will be employed as both a guide to the design of experiments and as an aid in the interpretation of experimental results. With this renewal award, the Synthetic Organic Program is supporting the research of Dr. David M. Lemal of the Department of Chemistry at Dartmouth College. Professor Lemal will focus his work on the synthesis and investigation of the chemistry of an array of highly fluorinated compounds. Replacement of the hydrogens in organic molecules by fluorine results in dramatic differences in both properties and chemical behavior. As a result, fluorocarbon chemistry has great commercial importance.