Question

Free radical halogenation?

Answer 1

http://www.chegg.com/homework-help/questions-and-answers/consider-structure-unnamed-organic-molecule-three-hydrogens-sets-hydrogen-atoms-identified-q3410074

I have that exact question

Answer 2

And I would suspect something similar that in general C> B > A, but shouldn' resonance be taken in to account? or am I being really dumb?

Answer 3

What stabilizes a radical intermediate? Just considering alkanes, a methyl radical is the most unstable, then increasing in stability is primary, secondary, then tertiary. This is similar to how carbocations are also more stable in tertiary rather than primary carbons.

But then even more stable than that is something with double bonds in it that can contribute to resonance. Allylic and benzylic positions are the most stable places to have a radical intermediate as they are resonance stabilized. you can draw arrows to show this for yourself.

Answer 4

So I sort of didn't directly answer you, but you're absolutely right. Resonance is very important to consider here and you're not being dumb. =P

Answer 5

So would it be B-C-A because of the double bonds directly next to that carbon?

Answer 6

I'm not sure I know what the question is. The problem doesn't look like one organic molecule, it's sort of weird.

Answer 7

Its connected at the bottom.

Answer 8

Its not super easy to see, I'll redraw it

Answer 9

From what you're saying and what I'm guessing the structure is supposed to be, that seems right.