[tomhall15]

Hey so im having some difficulty solving this problem...

Draw the product or mixture of products that result from the bromination of the given starting material with less than one equivalent of NBS in the presence of peroxides.

I submitted this answer and got it wrong...can someone tell me why?? THANKS

[azmanam]

you've got the right idea, even the resonance associated with the allylic radical.  In truth, probably some mixture of the two will result.  I suspect what your program is looking for is the one, dominant product. 

You've probably learned that in many respects radicals are similar to carbocations: electron poor, stabilized by more radical groups, able to participate in resonance, etc.  But they're different in some respects, too: 1,2-shift doesn't occur, for example.

Another point of difference is product distribution when the intermediate is resonance stabilized.  Carbocations will favor the product resulting from the more stable resonance contributor, while radicals will favor the most stable product, regardless of the resonance contribution of the intermediate.

So if you could narrow it down to one predominant product, which do you think it would be?