Amides Flashcards
Amide functional group
Carbon bonded to an amine group and a carboxylic acid
Primary amide
2 hydrogen is bonded to the nitrogen in the amine grouo
Secondary amide
On the nitrogen:
One hydrogen bonded
One alkyl group bonded
Tertiary amide
2 alkyl groups bonded to nitrogen
How can you make amides?
From acyl chlorides + ammonia/amine
Conditions for acyl chloride + amine/ammonia
Anhydrous conditions
Ethanolic amine/ammonia
Acyl chloride + ammonia products
Primary amide (2 hydrogen on the nitrogen)
And an ammonium salt
How is an ammonium salt formed from acyl chloride + ammonia?
Excess ammonia present (2 ammonia per 1 acyl chloride)
The first ammonia loses a hydrogen to form HCl (then bonds to the acyl chloride)
The second ammonia combines with HCl = NH4+Cl-
Acyl chloride + primary amine makes?
A secondary amide + alkylammonium chloride
How does primary amine + acyl chloride make an alkylammonium chloride salt?
Excess primary amine:
One hydrogen on amine eliminated so the AMINE can bond to acyl chloride and the hydrogen forms HCl gas with eliminated Cl
HCl reacts with second primary amine to form RNH3+Cl- salt
Acyl chloride + secondary amine makes?
A tertiary amide but NO SALT
Can secondary amine + acyl chloride form an alkylammonium salt?
No
Reactions of amides
Reduction to an amine
Hydrolysis under reflux under acid or alkaline conditions
Reduction of an amide conditions
4LiAlH4 in dry ether
And hydrolysis with dilute acid
Products of reduction of amide
Amine of same classification + H2O
Hydrolysis of amide under acid and reflux conditions
Amide + H+ + H2O ——> Carboxylic acid + ammonium ion
Hydrolysis of amide under alkaline conditions
Amide + OH- ——> Carboxylate ion + ammonia
What to do with carboxylate ion after producing it in the hydrolysis of amide
Protonate by reacting with a dilute acid to form a carboxylic acid
