Collect. Czech. Chem. Commun. 1990, 55, 1535-1540

Oxidation of 1- and 2-acetylnaphthalenes by iodate - a kinetic study

Prerepa Manikyamba

Department of Chemistry, Kakatiya University, Warangal - 506 009 (AP) India


Kinetics of oxidation of 1- and 2-acetylnaphthalenes by iodate in the presence of sulphuric acid in aqueous methanol has been studied. The reaction is first order with respect to both [iodate] and [acetylnaphthalene]. Solvent effect indicates a cation-dipole type of interaction in the rate limiting step. A mechanism is proposed with a slow attack of IO2+ on enol form of acetylnaphthalene forming an intermediate carbonium ion, which ultimately gives corresponding ω-hydroxyacetylnaphthalene. The higher reactivity of 2-acetyl isomer is attributed to the greater stability of the corresponding carbonium ion than that of 1-acetyl isomer.