Abstract
The oxidative pattern of α-hydroxy acids by acidic bromine water is shown to be similar to the oxalic acid – bromine water reaction. In both cases HOBr is the oxidant and the undissociated form of the organic acid is required for reaction to occur. The rate law −d[HOBr]/dt = k[HOBr][hydroxy acid] is observed for oxidations carried out in the presence of Ag+ ion in the pH range 2–5. Below that pH bromination occurs. Bell-shaped pH-rate profiles are obtained for the oxidations of benzilic, mandelic, and 2-hydroxy-2-methylpropanoic acids. The calculated rates, based on a steady state treatment of a reaction path involving a hypobromite intermediate (R2COBrCO2H) are in agreement with the observed values and with the observation that the rates of oxidation of mandelic acid in D2O and H2O are the same.
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