[xshadow]

Hi, I have some doubts about the reaction between an amise and an alcohol

Some textbooks say that there is no reaction because in the tethraedral intermediate  -OR is a better leaving group than -NH₂ ...so OR- is the leaving group and the amide is reformed

But other textbooks say that this is an equilibrium and this reaction  can occour anyway

So where is the truth?
Thanks!!

[rolnor]

Under acidic conditions the reaction goes to RCOOR and NH4+

[kriggy]

Under acidic conditions the reaction goes to RCOOR and NH4+

Do you have an example in the literature? I reacall hydrolyzying acetamides in refluxing KOH overnight so its likely needs some harsh conditions but I never heard of this conversions you are describing

[rolnor]

Under acidic conditions the reaction goes to RCOOR and NH4+

Do you have an example in the literature? I reacall hydrolyzying acetamides in refluxing KOH overnight so its likely needs some harsh conditions but I never heard of this conversions you are describing

No, I dont but I have boiled amides in conc. HCl and you get the acid. If you have conc H2SO4 im MeOH you will get the ester I think.

[spirochete]

I'd guess it's a difficult reaction in practice, but I've read that you can do the conversion in acid because there is a driving force to remove the amine/ammonia from the equilibrium by protonation.

[kriggy]

Under acidic conditions the reaction goes to RCOOR and NH4+

Do you have an example in the literature? I reacall hydrolyzying acetamides in refluxing KOH overnight so its likely needs some harsh conditions but I never heard of this conversions you are describing

No, I dont but I have boiled amides in conc. HCl and you get the acid. If you have conc H2SO4 im MeOH you will get the ester I think.

I wouldnt be surprised if I got some diethylether or methlytation products instead of the ester.

I'd guess it's a difficult reaction in practice, but I've read that you can do the conversion in acid because there is a driving force to remove the amine/ammonia from the equilibrium by protonation.

Yeah, I think its gonna be hard to force the addition to the carbonyl.  I know you can to it when its tertiary amide with strong EWG group like tosyl or boc which kinda reduces the conjugation of the lone pair but otherwise not easy