Potassium-graphite, a typical alkali metal-graphite intercalation compound, has been found to undergo reactions with organic substrates y both one-and two-electron processes. The reaction of weak protic acids like water and alcohols with C[subscript 8]K proceeds both by simple deprotonation of the protic acid by the Lewis base C[subscript]K to give a partially reduced graphite and by the reduction leading to the hydrogen formation. ESCA spectra of the graphite product of these reactions, titrations of the soluble based in these reactions of C[subscript 8]K and proton sources, and measurement of the amount of hydrogen evolved on reaction of C[subscript 8]K and an alcohol all suggest that the reactivity of C[subscript 8]K toward proton acids is substrate size dependent. In general, Lewis base abstraction of a proton by C[subscript 8]K seems to be more important with smaller alcohols. One-electron processes may be relatively more important in reactions of larger alcohols at the surface or edges of C[subscript 8]K. The acid-base chemistry of rubidium-graphite and cesium-graphite was shown to be similar to that observed for C[subscript 8]K. ...
