a-Fluorocarbanions are key intermediates in nucleophilic fluoroalkylation reactions.A lthough frequently discussed, the origin of the fluorine effect on the reactivity of afluorinated CH acids has remained largely unexplored. We have nowinvestigated the kinetics of aseries of reactions of asubstituted carbanions with reference electrophiles to elucidate the effects of a-F, a-Cl, and a-OMe substituents on the nucleophilic reactivities of carbanions.