NMR determination of the kinetics of deuterium exchange in 3-methyl-2-butanone

CHED 435

Amy Knutson, 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-methyl-2-butanone is a case of competing reactions with very different rates. The alpha methyl protons are much more readily exchanged than the isopropyl methine proton. The disappearance of the alpha methyl protons are followed directly. The disappearance of the methine protons are more readily followed indirectly by monitoring changes in the beta methyl groups. The initial doublet with a splitting slightly above 7 Hz is replaced by a triplet at the center with a splitting of ~ 1Hz due to the replacement of the proton with deuterium. The disappearance of the doublet components is more readily followed than the disappearance of the heptet corresponding to the methane resonance.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.