Electra
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Are all formamids unstable in the prescense of water?
I've read that normal formamide is unstable in water and hydrolyzes (or am I mistaken?), but does this happen to substituted (alkyl and alkyl-aryl)
formamides as well? Or do substituted formamides behave like any other amide around water?
[Edited on 13-4-2016 by Electra]
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Dr.Bob
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Formamides covers a lot of ground, but I have made some in the past, of alkyl amines, and they are stable to water for short times, like extractions
and reaction workups. Most will slowly hydrolyze in water or humid air, but not quickly. I have actually had some hindered ones that take boiling
6N HCl to hydrolyze, which is pretty harsh. And DMF (dimethylformamide) is pretty water stable, although I rarely leave it mixed in water except
when I am trying to wash it away from a reaction workup.
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Electra
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I am guessing the hydrolysis would occur by nucleophilic attack of the water, so maybe if the molecule is electron rich enough, it could be
stabilized.
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