Allylic bromides, from alkenes isomerization

An allyl radical can be brominated at both termini of the radical. This is why two allyl bromides can result from the Wohl-Ziegler bromination of an alkene if the allyl radical intermediate is unsymmetrical (examples see Figures 1.29-1.31). Even more than two allyl bromides may form. This happens if the substrate possesses constitutionally different allylic H atoms, and if, as a result thereof, several constitutionally isomeric allyl radicals form and react with bromine without selectivity. 

PROBLEM 10.5 The two alkenes 2,3,3-trimethyl-1-butene and 1-octene were each subjected to allylic halogenation with A/-bromosuccinimide. One of these alkenes yielded a single allylic bromide, whereas the other gave a mixture of two constitutionally isomeric allylic bromides. Match the chemical behavior to the correct alkene and give the structure of the allylic bromide(s) formed from each. 

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