A reinvestigation of the reaction between Prop-2-en-1-ol and chloramine-T in hydrochloric acid medium

Contrary to a previous report the reaction of prop-2-en-1-ol with chloramine-T in 1 M HCl gives 2,3-dichloropropan-1-ol not prop-2-en-1-al. For HCl concentrations of 0.075 M and higher the reaction is of first order each with respect to the concentration of chloramine-T, H+ and Cl- ions, but independent of the alcohol. As chloroamines in these conditions are known to give chlorine, it is proposed that the reaction involves the addition to the unsaturated alcohol of molecular chlorine which is produced by a prior, rate-determining reaction between H+ and Cl- ions with chloramine-T.