Amide formation from acid and amine

Reaction class

Amidation

Typical conditions

Usually requires a coupling reagent or strong heating; direct condensation is slow.

Mass balance

balanced — the co-products are written out, not dropped

Mechanism

Nucleophilic acyl substitution, 3 steps

Conditions are what the literature ordinarily uses, recorded so you can see whether yours are in the usual range. They are not a procedure and they are not scaled to your flask.

The nucleophile adds to the carbonyl, the carbon holds four groups for a moment, and the leaving group is pushed out as the double bond comes back.

1. 1The nucleophile attacks the carbonyl carbon
2. 2The carbonyl comes back and the leaving group goes
3. 3A base takes the proton

This is the pathway taught for the class, not a record of what was observed. On the platform it is drawn on the structures you supply, with the curly arrows on the atoms that actually move.