RUI: Stereochemical Determinants in Elimination and Proton Transfer Reactions

Carleton College, Northfield MN

Investigators

Abstract

With this Research at Undergraduate Institutions award, the Organic and Macromolecular Chemistry Program is supporting Professor Jerry R. Mohrig, of the Department of Chemistry at Carleton College, for his studies of stereochemical determinants in elimination and proton transfer reactions. These studies, focused on the stereochemistry of addition and elimination reactions involving beta-substituted esters and thioesters of butyric acid and the related aldehydes and ketones, seek a comprehensive understanding of the stereochemical consequences of the carbonyl group and substituents at C-3 on the stereochemistry of addition-elimination and proton transfer reactions involving acyclic beta-substituted carbonyl compounds. In research to be carried out by a group of undergraduate chemistry majors, the importance of substrate acidity and the leaving group in determining the stereoselectivity of base-catalyzed 1,2-elimination reactions producing conjugated carbonyl compounds will be explored through a combination of synthetic and NMR spectroscopic studies. Similarly, the stereochemistry of electrophilic attack at enolate anions will be investigated. Understanding and controlling the three-dimensional structure of noncyclic molecules remains an inportant challenge in organic chemistry. Within this context, the stereochemical details of reactions involving the addition to or elimination of fragments from molecules are of both fundamental interest and relevance to numerous biologically catalyzed processes. Professor Jerry R. Mohrig, of the Department of Chemistry at Carleton College, is supported by a Research at Undergraduate Institutions award from the Organic and Macromolecular Chemistry Program for his studies related to the stereochemistry of such reactions. Through a combination of synthetic and spectroscopic studies, carried out by undergraduate chemistry majors, Professor Mohrig is developing a detailed understanding of these important chemical processes while simultaneously providing undergraduates with the opportunity to carry out research on fore-front, significant problems.