Computational studies have been used to examine the structural and energetic effects of adding small numbers of water molecules to methanol, tert-butyl alcohol, methoxide, and tert-butoxide. The effective fragment potential as well as Hartree-Fock methods reveals distinct:structural effects with as few as two to four water molecules. Structural and energetic effects are used to probe the acidity reversal of simple aliphatic alcohols on going from the gas phase to protic solvents. Although the effective fragment potential and Hartree-Fock methods without sufficient electron correlation underestimate the number of water molecules that give rise to acidity reversal, the trend toward reversal is evident with small numbers of waters in all methods.