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Topic: Treating Cyclohexene with Dibromine  (Read 1983 times)

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Offline Hijaz Aslam

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Treating Cyclohexene with Dibromine
« on: November 17, 2014, 11:50:35 AM »
1.



Can I know the mechanism of the above reaction?

2.



Why does the Bromine gets attached to Carbon 1 in the diagram? Why not Carbon 2?


Offline kriggy

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Re: Treating Cyclohexene with Dibromine
« Reply #1 on: November 17, 2014, 03:10:50 PM »
When you see UV light in reaction conditions its always (or almost always?ยจ) radical mechanism.
What do you know about stability of radicals?

Offline OrgXemProf

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Re: Treating Cyclohexene with Dibromine
« Reply #2 on: November 22, 2014, 06:26:24 PM »
In the light (no pun intended!) of kriggy's suggestion, consider the first reaction (cyclohexene + Br2 + heat/UV light):

What product(s) would be expected to be formed if 1-deuteriocyclohexene had been used as starting material instead of (unlabeled) cyclohexene?

Then, consider the second reaction (para-nitroethylbenzene + Br2 + heat/UV light):

Would you expect alpha-bromination to occur faster, slower or at about the same rate if para-methoxyethylbenzene had been used as starting material instead of para-nitroethylbenzene?


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