NMR determination of the kinetics of deuterium exchange in 3-pentanone

CHED 436

Giancarlo Toledanes and Thomas B. Malloy Jr., malloyt@stthom.edu. Department of Chemistry, University of St. Thomas, 3800 Montrose Blvd, Houston, TX 77006
The analysis of the base catalyzed exchange of the alpha protons in 3-pentanone yields a classic case of consecutive reactions with the second rate constant being smaller than the first. It was possible to independently follow the appearance and subsequent disappearance of partially exchanged species. The exchange process may be represented as the disappearance of a reactant A, the normal isotopomer, appearance and subsequent disappearance of an intermediate B, which is any species with CHD in the alpha position, followed by the appearance of the product, C with two D's in the alpha position. The disappearance of A, appearance and disappearance of B and appearance of C were all followed independently by monitoring and integrating different regions in the methyl region of the spectrum. This experiment can easily be completed in one undergraduate laboratory period. We are currently using this as a physical chemistry laboratory experiment.Partial support for this work was provided by the National Science Foundation's Course, Curriculum, and Laboratory Improvement program under Award No. 0536648. The Welch Foundation is acknowledged for support.