Amide mechanism

[airstrikee]

When we have an amide, let's use acetamide as an example. If we were to treat acetamide with an acid (let's say with hydronium), why is the first step to protonate the oxygen? Why would we not protonate the nitrogen first since it is more basic? Why is oxygen more readily protonated?

 

[Hadi7183]

Amide's nitrogen is almost non-reactive, because its lone pair is involved in conjugation with carbonyl's pi-bond.

 

[exacto]

also to add to hadi, the carbonyl is almost always the first place to look in o-chem problems...chances are if there is a carbonyl group, something is gonna happen there since it is polar and easily reactable with many compounds...kinda like a cheat hint...lol