Halogenation of acetone. A method for determining pKas of ketones in aqueous solution, with an examination of the thermodynamics and kinetics of alkaline …

JP Guthrie, J Cossar, A Klym

Index: Guthrie, J. Peter; Cossar, John; Klym, Alex Journal of the American Chemical Society, 1984 , vol. 106, # 5 p. 1351 - 1360

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Citation Number: 27

Abstract

Abstract: The pKa of a simple ketone can be determined by analysis of the kinetics of halogenation in alkaline solution (J. Am. Chem. Soc. 1982, 104, 895). Details of the determination of the pKa of acetone are reported. The stoichiometry of chlorination of acetone is 2.15 hypohalites per acetone; bromination consumes 2.83 hypobromites. The major product from chlorination is lactate and not acetate; lactate is a minor product from ...