Nucleophilic substitutions in mixed solvents. Part III. The ethanolysis of acid chlorides in solvolytic media

Abstract

The rate of ethanolysis of p-nitrobenzoyl chloride measured in the non-associating solvents carbon tetrachloride, cyclohexane, and benzene and the associating solvents, diethyl ether, dioxan, acetone, acetonitrile, and nitromethane is approximately proportional to the concentration of associated alcohol. No definite decision between a molar and a mole fraction scale is made, although molarity appears to be more satisfactory for high degrees of association. In associating solvents, the apparent order with respect to alcohol gives the solvation number in part of the solvolytic range. The limitations of this treatment are discussed.