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Topic: Free Radical Bromination  (Read 6720 times)

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Offline Ankesh

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Free Radical Bromination
« on: May 02, 2010, 01:45:47 AM »
What will be the product and how when Cyclohexene reacts with Br2 in presence of heat and UV light?

Offline Yasimara

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Re: Free Radical Bromination
« Reply #1 on: May 02, 2010, 03:59:56 AM »
The UV would produce two bromine radicals, one of which would (non-selectively) remove a hydrogen from the cyclohexane to form an HBr molecule, and a reactive carbon radical. The carbon radical would react with another bromine radical to produce a cyclohexane ring with one of the hydrogens replaced with a bromine. This reaction can continue to produce a further brominated ring depending on temperature, concentration, etc.

Offline Schrödinger

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Re: Free Radical Bromination
« Reply #2 on: May 02, 2010, 10:04:05 AM »
The UV would produce two bromine radicals, one of which would (non-selectively) remove a hydrogen from the cyclohexane to form an HBr molecule, and a reactive carbon radical. The carbon radical would react with another bromine radical to produce a cyclohexane ring with one of the hydrogens replaced with a bromine. This reaction can continue to produce a further brominated ring depending on temperature, concentration, etc.
The OP was referring to cyclohexene, not cyclohexane. But in general, what you said is true.
In the case of cyclohexene, carbon - 3 will be attacked because that particular free radical intermediate is more stable :



than the other ones that are possible
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