Reactivity in nucleophilic substitution. Part II. Kinetics and mechanism of the hydrolysis of 9-fluorenyl toluene-p-sulphonate in aqueous acetone

Abstract

The hydrolysis of 9-fluorenyl toluene-p-sulphonate has been studied in various aqueous-organic solvents. In 90% aqueous acetone there is a linear relation between the specific rates of hydrolysis and the concentration of added LiClO₄ or NaBr. For the same solvent the alpha deuterium kinetic isotope effect k_H/k_D= 1·14. Increasing the water content of the solvent increased the rates of hydrolysis and all these observations are taken to substantiate a classical S_N1-type reaction for the rate-determining process.