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Micellar sodium dodecyl sulfate (SDS) affects selectively three competing processes in the change of configuration at the chiral carbon in the oxygen exchange reactions of 1-phenyl-1-ethanol and 1-phenyl-1-butanol in aqueous media. Here, micellar SDS decreases substitution with inversion, enhances substitution with retention, and does not alter inversion without substitution. The results agrees with the predicted k(sub EI). It was observed that micellar SDS increases k(sub E) for both alcohols, by affecting hydrophobic 1-phenyl-1-butanol.

HPLC and GC/MS studies reveal the rate constants of three competing reactions in acid-catalyzed water exchange reactions of 1-phenyl-1-alkanols. Analysis of the oxygen exchange reaction kinetics of (18)O-labeled phenylethanol in water yields rate constants for the three processes. These oxygen-exchange reactions are enantiomer-specific. The influence of alkyl substituents on the solvation sphere of the intermediate carbocation is also examined.