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Author: Subject: Mechanism of urea hydrolysis
Yorty2040
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[*] posted on 14-5-2024 at 16:23
Mechanism of urea hydrolysis


I was always under the assumption that urea hydrolyzed by hydroxide performing nucleophilic attack on the carbonyl to form a tetrahedral intermediate, then proton transfer, then expulsion of ammonia as a leaving group to form carbamic acid, then proton transfer to form the zwitterion, then lysis of the carbon-nitrogen bond to form ammonia and CO2.

But apparently that's not the case, and there are conditions where it can actually break down via an isocyanate intermediate? I understand the precise mechanism and rates are very pH dependent, but it's been awhile since Org Syn classes and I'm very rusty with mechanisms.

[Edited on 15-5-2024 by Yorty2040]
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