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Topic: Solvolysis of benzhydryl bromide in DMSO  (Read 4209 times)

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ptb969

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Solvolysis of benzhydryl bromide in DMSO
« on: May 24, 2006, 12:48:28 PM »
Hallo,
what do you think would happen if you put benzhydryl bromide in DMSO?
I appreciate very much your suggestion.
PTB
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Offline Dan

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Re: Solvolysis of benzhydryl bromide in DMSO
« Reply #1 on: May 24, 2006, 01:33:34 PM »
What do you think would happen?
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ptb969

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Re: Solvolysis of benzhydryl bromide in DMSO
« Reply #2 on: May 26, 2006, 06:56:02 AM »
Well, as a matter of fact, I think that benzhydryl bromide would be ionized and carbocation would be formed, subsequently the carbocation would be rapidly trapped by DMSO to form so-called oxosulfonium ion which reacts quickly with water releasing benzhydrol. So it should behave in a like SN1 manner.
PTB
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Offline Dan

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Re: Solvolysis of benzhydryl bromide in DMSO
« Reply #3 on: May 26, 2006, 08:54:58 AM »
That sounds sensible to me.
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