The compositions of dibromide mixtures obtained from the polar bromination of cyclopentadiene, 1,3-cyclohexadiene, and (Z,Z)~, (E,Z)-, and (S,E)-2,4-hexadiene under conditions of kinetic control have been determined. Compositions of equilibrated products were also determined. The stereochemistry of 1,4 addition is found to be primarily cis. The extent of 1,4 addition, which occurs cis, is highest with 1,3-cyclohexadiene and lowest with cyclopentadiene (96 and 52%, respectively, in carbon tetrachloride). The extent of cis 1,4 addition to the 2,4-
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