Acid-Catalyzed Hydration of Prop-2-en-1-ol and 2-Methylprop-2-en-1-ol: Correlation of Reactivity

Abstract

The kinetics of the acid-catalysed reaction of prop-2-en-1-ol and 2-methylprop-2-en-1-ol have been measured. The relative reactivity, solvent isotope ( ^kH+/^kD +) and change in acidity effects, and activation parameters, have been determined and found to be similar to those of other alkenes. While this correlation of results for the hydration of both these alkenols can be interpreted in terms of the conventional Ad-E2 mechanism, computed values for the lifetime of possible carbocation intermediates suggest that an alternative mechanism for the reaction of prop-2-en-1-ol, in which nucleophilic attack by the solvent is concerted with protonation, is feasible.