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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: carotis on October 01, 2016, 07:23:04 PM

Title: would Br get substituted by H2O in N(Et)3 ?
Post by: carotis 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?

Title: Re: would Br get substituted by H2O in N(Et)3 ?
Post by: AWK on October 01, 2016, 11:41:53 PM

Et₃N is alkylated by RBr. For hydrolysis of RBr use strong base.

Title: Re: would Br get substituted by H2O in N(Et)3 ?
Post by: rolnor 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.

Title: Re: would Br get substituted by H2O in N(Et)3 ?
Post by: carotis on October 02, 2016, 09:21:48 PM

thanks