Imine hydrolisis

Imines are usually extremely unstable, unless they are structurally particularly stable, like coniugated π system.

sintesi-immina

Is extremely difficult to isolate them, because they are easily hydrolized. Resuming, starting reagents in imine synthesis reaction, aldehyde (or ketone) and amine are much more stable than the imine itself;

immina instabile

Here it is the imine hydrolisis reaction mechanism:

meccanismo-idrolisi-immina

 

1) The imine is protonated. Iminium ion is very likely to be attacked by a nucleophile.

2) The nucleophile in this case is H2O, which attacks the iminium ion with π C−N bond break and forming of a new σ C−O bond.

3) There must be an inter o intramolecular protons exchange. Hydroxyl get rid of the charge while the amine become a good leaving group.

4) The oxonium ion loses a proton.

 

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