Abstract
A mechanism is proposed for the fast product-forming step of the bromination of alkenes in which a bromonium ion catalyzes the formation of a vicinial dihalide product. Energy profiles for this step of the syn and anti addition of molecular bromine to alkenes with various levels of substitution at the double bond were investigated using density functional theory calculations. Our calculations were able to reproduce experimentally observed trends in reactivity as a function of double-bond substitution. We additionally demonstrate that the anti addition is kinetically more favorable and results in the trans product, in agreement with experiment. The mechanism described here provides another route to the halogenated product which does not necessitate the formation of a new counteranion for each product molecule that is formed, and the highly exothermic nature of this step could serve to drive other reactions forward in a similar way.
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