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Topic: would Br get substituted by H2O in N(Et)3 ?  (Read 1176 times)

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Offline carotis

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would Br get substituted by H2O in N(Et)3 ?
« on: October 01, 2016, 07:23:04 PM »
Hello, I should show a theoretical evidence: Is N(Et)3 a good medium to induce a substitution reaction? I guess since it is described as a basic solvent, a reaction like H2O/H+ wouldnt make any sense, isn't it?
Otherwise I would assume a kind of reaction mechanism like:
²°R-Br -> R+ + H2O -> R-H2O+ + H2O --> R-OH + H3O+

But the Et3N would neutralize this reaction right? In other words, under basic conditions would the substitution occur? How can I imagine the mechanism?

Offline AWK

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Re: would Br get substituted by H2O in N(Et)3 ?
« Reply #1 on: October 01, 2016, 11:41:53 PM »
Et3N is alkylated by RBr. For hydrolysis of RBr use strong base.
AWK

Online rolnor

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Re: would Br get substituted by H2O in N(Et)3 ?
« Reply #2 on: October 02, 2016, 07:44:18 AM »
There are halides that would be hydrolysed, I believe tritylchloride and methoxymethyl chloride would be but that is special cases.

Offline carotis

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Re: would Br get substituted by H2O in N(Et)3 ?
« Reply #3 on: October 02, 2016, 09:21:48 PM »
thanks

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