In order to understand the mechanism of free radical graft reactions onto high molecular weight polyolefins, squalane and related small molecules have been examined. Characterization of polyolefins with less than 5% grafted functionality is extremely difficult, and has been one of the major reasons for using smaller molecules in mechanistic studies. In this paper the free radical bromine graft reactions onto squalane, methylhexane and nonane in the presence or absence of an initiator are discussed. Multiple brominations were preferred at the same site, because of the acidic proton alpha to the bromide moiety. Material characterization by modern techniques as well as a possible radical reaction pathway have been suggested.