Kinetic studies of Dakin oxidation of o- and p-hydroxyacetophenones

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Abstract
Rates of oxidation of aqueous o-, and p-hydroxyacetophenone with alkaline hydrogen peroxide to yield catechol and hydroquinone, respectively, have been followed spectrophotometri-cally. Both ketones showed smooth pseudo first-order behaviour, the ortho isomer yielding rate constants in the range 2.6 to 6.6 × 10−2 min−1 at 0 °C, and the para isomer of 0.73 to 7.10 × 10−2 min−1 at 35 °C for the concentrations of hydrogen peroxide and base used. The order in hydrogen peroxide was, unexpectedly, found to be 1.4. A simple test established that this fractional order was probably not the result of hydrogen peroxide involvement in simultaneous first- and second-order processes of differing rates. Other plausible pathways to explain this are proposed.

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