The reaction of bromine with cyclohexene in carbon tetrachloride. Part 2. Reactions in the presence of added hydrogen bromide, and of imides, and in the absence of additives

Abstract

The addition of bromine to cyclohexene in carbon tetrachloride containing added hydrogen bromide takes place rapidly, and is of first order in each of these species. When bromine is added to cyclohexene in solutions containing succinimide or phthalimide, the addition reaction follows an expression of order 1.5 in bromine and 0.5 in the imide. When no other component is present, the addition of bromine to cyclohexene is extremely sensitive to unintentional additives, but is usually of order 1.5 in bromine and of small positive order in water. We suggest reasonable reaction mechanisms for these processes, involving species stoicheiometrically equivalent to HBr₃ and HBr₅, and discuss their applicability to the second, fast phase of the scavenged reactions described in Part 1.