Hydrogen halides add to alkenes yielding the corresponding haloalkane.
The addition of HX ordinally follows the course of Markownikoff's rul
e. In this paper we analyze the HBr addition reaction to unsaturated c
arboxylic acids. The course of the addition is anti-Markownikoff. This
implies that the reaction goes through free radical mechanism and the
haloacid formed is in the beta-position. The acids under study are fu
maric, itaconic, citraconic acids and the methyl ester of fumaric acid
. The beta-haloacids formed are easily purified from the bulk solution
s.