Abstract
The mechanism of oxidative decarboxylation of 2-hydroxy-2-phenylethanoic acid (mandelic acid) by aqueous alkaline sodium hypochlorite (commercial bleach) has been studied. Kinetic studies for a series of 4-substituted mandelic acids (CH 3 O, CH 3 , H, F, Cl, CF 3 , NO 2 substituents) gave a Hammett o value of −0.23. When deuterium was substituted for hydrogen on the α-carbon atom of mandelic acid, a secondary kinetic isotope effect, (k H /k D ), of 1.07 was obtained. On the basis of these results a model for the transition state is proposed
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