Acetolysis of the p-Toluenesulfonates of the 2,3-Butanediols

Proton‐Assisted Ethylene Hydration in Aqueous Solution

“…Consequently, the reverse reaction, that is, the proton-assisted dehydration of ethanol, is an E2 elimination reaction. The calculated hydration activation energy of 23 kcal mol À1 is near the experimental values for the activation barriers of the hydration of isobutene [14] (23 kcal mol À1 ) and 2-methyl-2-butene [15] (19 kcal mol À1 ) in acidic solution. Figures 2 and 3 show that the trajectory at q = 0.11 along the hydration route and the trajectories at q = 0.05 and 0.00 along the dehydration route exhibit reactive events with the force on the protontransfer coordinate changing sign and the CÀO bond either forming or breaking.…”

Solvolytic Displacement Reactions At Saturated Carbon Atoms

“…This result has been plausibly interpreted as a reaction of CXIX with water to form an orthodiacetate (CXX), which subsequently opens to give cis-2-acetoxycyclohexanol (674). Much the same result is obtained C& CH, (438), and cyclopentane and indane derivatives (686). Neighboring acetoxy participation has been suggested to explain some reactions in the carbohydrate series (347,498).…”