The chlorination of acetone: a complex kinetic analysis

Article abstract of DOI:10.1139/v86-208

Rate constants are reported for all of the major steps followed in the chlorination of acetone, including the chlorination of mono- and 1,1-dichloroacetone, the chlorination of hydroxyacetone, the chlorination and hydroxide-catalyzed rearrangement of 1,1-dihydroxyacetone, and the haloform cleavage of trichloroacetone. pK_a values are reported for hydroxyacetone and monochloroacetone.Rate constants for the hydrolyses of chloroacetone and 1,1-dichloroacetone are reported; these reactions are probably not S_N2 displacements but proceed by addition of hydroxide and intramolecular displacement.