[pressplay312]

What is the major bromination product for this molecule?  Thanks.

[sjb]

What is the major bromination product for this molecule?  Thanks.

(propylbenzene, in case the image disappears)

Under what conditions?

[pressplay312]

Under heat and light.  The answer in the book places the Br at the first propyl C and I have no idea why!

Thanks...

[discodermolide]

Under heat and light.  The answer in the book places the Br at the first propyl C and I have no idea why!

Thanks...

What does heat and light RADICALLY do to bromine?

[pressplay312]

Are you asking about the initiation step--homolytic cleavage?

I'm just wondering why the major organic product is the first propyl carbon and not the second, since they're both secondary.

[discodermolide]

Are you asking about the initiation step--homolytic cleavage?

I'm just wondering why the major organic product is the first propyl carbon and not the second, since they're both secondary.

Think about the stabilization of the radicals formed, which one can be better resonance stabilized?

[pressplay312]

The C1 on propyl is surrounded by a gigantic ring and a CH2.  The C2 on propyl is surrounded by a CH2 and CH3.  I'm not sure how resonance plays a role here, but I'm guessing since the C1 would have more hyperconjugation, it's an overall more stable radical?

[pressplay312]

Hey so my exam's in 2 hours.

HELLLLLLLLLP

lol.

[discodermolide]

The C1 on propyl is surrounded by a gigantic ring and a CH2.  The C2 on propyl is surrounded by a CH2 and CH3.  I'm not sure how resonance plays a role here, but I'm guessing since the C1 would have more hyperconjugation, it's an overall more stable radical?

The radical next to the benzene ring , the benzylic carbon atom, is the more stable one, try moving the pi electrons around.