19F-NMR investigation of the addition reactions of 2,2,2-trifluoroacetophenone

CHED 220

Kurt W. Field, kwf@bradley.edu and Kara M. Williams. Department of Chemistry and Biochemistry, Bradley University, 1501 W. Bradley Ave., Peoria, IL 61625
We are developing experiments for undergraduate laboratories that will utilize the multinuclear capabilities of most contemporary NMR spectrometers. Specifically, we are investigating the effect of solvent (acetone, dimethyl sulfoxide, N,N-dimethyl formamide, dioxane, acetonitrile, and diethyl ether) on the position of the equilibrium and the rate of addition for the hydration (H2O and D2O) of 2,2,2-trifluoroacetophenone. We have found the equilibrium positions to be solvent sensitive and the rates of addition to be isotope sensitive. Further studies will involve the nucleophilic addition of alcohols to the ketone and an Arrhenius study to determine the thermodynamic parameters for these reactions.