Mechanism of the oxidation of para-substituted 1-phenylethanols with sodium hypochlorite in acetic acid

The ρ-value of −1.8 for the oxidation of para-substituted 1-phenylethanols by sodium hypochlorite in acetic acid suggests that ketone is formed directly from alcohol by loss of a hydride. The kinetic isotope effect is 3.0. When the disappearance of oxidant is followed by iodometric titration, 5-nonanol is oxidized about 20 times faster than 1-butylpentyl hypochlorite decomposes. However, when NaCl is added to the alkyl hypochlorite, the reaction rates are about the same.