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Topic: what would happen if to this compound in OH radicals?  (Read 1991 times)

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Offline iScience

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what would happen if to this compound in OH radicals?
« on: March 20, 2014, 07:13:49 AM »
hi, i just wanted to know what would happen if i had the following compound in a solution of OH radicals.

thanks
« Last Edit: March 20, 2014, 07:26:37 AM by Arkcon »

Offline TheUnassuming

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Re: what would happen if to this compound in OH radicals?
« Reply #1 on: March 20, 2014, 09:00:02 AM »
What are some reactions that OH radicals are known to execute with the given substrate?
When in doubt, avoid the Stille coupling.

Offline ThePostDoc

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Re: what would happen if to this compound in OH radicals?
« Reply #2 on: March 20, 2014, 09:59:59 AM »
Radicals only do a few things.  Halogen abstraction, proton abstraction, reproportionation, adding to alkenes and alkynes.   
In your molecule, you pretty much have two kinds of protons.  Is it going to do proton abstraction from the 2° carbon or the 3° carbon is the basis of this question. 

I am unsure about how selective the hydroxidy radical is, but the bromine radical would exlcusively abstract the 3° proton.  Chlorine is around only 60% for that proton.  The fact that you have 2 protons on a 2° carbon makes it statistically more likely, but the 3° carbon-H bond is weaker making it easier to abstract. 

Offline kriggy

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Re: what would happen if to this compound in OH radicals?
« Reply #3 on: March 20, 2014, 01:40:47 PM »
To my knowledge hydroxyl radical is very reactive so it doesnt differentiate much IMO. I suppose you get mixture of many products

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