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So I have this homework question which I'm fairly sure I'm correct with, but apparently there are 4 choices. I think the bond wants to be most substituted so it moves around so would the correct choices be: A, E, F & G?

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    $\begingroup$ I think it should be A,C,F,D ,though I am not sure. I'll do some review and get back. $\endgroup$ – Satwik Pasani Feb 8 '14 at 5:28
  • $\begingroup$ Thank you, I agree with A, C, and F wondering why it cant be G or E :/ confusing. $\endgroup$ – Harry Johnson Feb 8 '14 at 6:13

Your comment shows that you are on the right track.

You have chosen A and C because they are formed when the initial allylic radical instantaneously reacts with $\ce{Br2}$ in the propagation step of the reaction, isn't it? (Hint: Just say YES!)

Now give the allylic radicals corresponding to A and C a bit of time, just enough to flip the dot.

How do these other radicals look like? There you have the other two products.

For an extra point: Which isomer of methylcyclopentene could lead to G?

  • $\begingroup$ Thanks! It was in fact: A, C, F & D. Thank you for your advice. $\endgroup$ – Harry Johnson Feb 8 '14 at 23:16

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