On the mechanism of the reaction between ozone and alcohols: Ozonation kinetics of butanol-1 and its esters in CCl4

The ozonation kinetics of butanol-1, tributyl borate, butyl acetate, and butyl trichloroacetate was studied in the temperature range from -20 to 45A degrees C. The reactivity of the alpha-methylene group of the n-butyl moiety decreases in going from the alcohol to its trichloroacetic ester. In butyl trichloroacetate, this group is deactivated to such an extent that the kinetic parameters of the ozonation of this ester are comparable to the parameters observed earlier for n-butane. This decrease in reactivity is due the fact that the preexponential factor in the rate constant of the initial formation of an ozone-substrate complex decreases on passing from the alcohol to its esters. The activation energy of this process is constant within the error of data processing. It is concluded that the high reactivity of alcohols toward ozone is due to the initial formation of the ozone-substrate complex involving the hydroxyl group of the latter.