The kinetic study between paracetamol and N-chloro-p-toluenesulfonamide (chloramine-T) in the presence of an osmium(VIII) catalyst has been performed in an alkaline medium. The reaction exhibits second-order nature and the catalyst's effect indicates an uncatalyzed reaction simultaneously. The rate is retarded by hydroxide ions. The oxidation product to be quinone oxime is confirmed spectrally in stoichiometry where two moles of oxidant are required for each mole of the substrate. The thermodynamic quantities have also been computed using the Eyring equation. A plausible reaction mechanism is suggested accounting for all the experimental observations. To further support our proposed mechanism, density functional theory (DFT) computations at M06/6-311*G show that activation energy barriers predict the same reactivity trend as shown by the kinetic experiments.