Free radical bromination

[Ferferi]

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Which one undergoes free radical bromination most rapidly ? A primary carbocation or a tertiary one?
I guess I learned from chad's videos that bromine radical goes for the most substituted carbon. But now I see the same question in OAT sample test and the answer is CH4.

I really appreciate if someone tell me which one is correct?

 

[DrRoyal Pains]

Like you said, bromination is very selective (as opposed to chlorination), so it will attack the most substituted position. Thats weir'd that the OAT has that. Maybe it's an error? I know the 2007 and 2009 DAT has a bunch of errors, so I wouldn't be surprised if this is a mistake as well.

 

[Dotoday]

This should be a radical not a carbocation. Most of the time Bromine goes to the most stable (aka. Most substituted radical). However in case to toluene, it will go on the primary benzylic radical in order not to destroy aromaticity. If it would have gone to a tertiary carbon, the aromaticity ( stability) of the ring would have been destroyed. Hope this helps.

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