Achiever Orgo Question

[stillincollege]

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Hi,

In the picture above, it shows one achiever orgo question. I understand that free radical is more stable on the tertiary carbon, however, why is Br rather than H attached first? Why the reverse is wrong?

 

[unknown111]

Check this site out. It may help you to understand your question.
http://chemwiki.ucdavis.edu/Wikitex...Additions--Anti-Markovnikov_Product_Formation

Remember that this reaction most likely occurs in conjunction with hydrogen peroxide. So in your initiation step, you would form bromine radicals.

 

[stillincollege]

Thanks. It makes sense now...

 

[ktran17]

To remember that radicals are more stable due to hyperconjugation, just pretend that its slightly partially positive because it has one less electron. I don't know how true this is, but thats how i remember its trend follows carbocation trends =)