Intermediate Topic 815 of 1102 Organic Chemistry
Amides
Compounds with carbonyl bonded to nitrogen, stabilized by resonance and found in proteins.
In-depth explanation of Amides
Amides have the general formula RCONR2, in which a carbonyl is bonded to a nitrogen atom. The C-N bond has partial double-bond character because the nitrogen lone pair is delocalized into the carbonyl group, which makes the C-N bond planar and rigid. This resonance makes amides much less basic than amines and resistant to hydrolysis under mild conditions. Primary and secondary amides form hydrogen bonds through their N-H groups, and the amide link is the backbone of nylon and of proteins.
Going deeper: Amides
Key ideas: RCONH2 has a strongly delocalised nitrogen lone pair, giving a planar structure, a partial C-N double bond (rotation barrier about 75 kJ/mol), and almost no basicity (pKa of conjugate acid about minus 0.5). Hydrogen bonding raises melting points (acetamide 82 C). Prepared from acid chlorides with amines, hydrolysed under hot strong acid or base, reduced by LiAlH4 to amines, and dehydrated by P2O5 to nitriles.
Common mistakes and connections: Students call amides basic like amines, or assume free C-N rotation, which matters in peptides. Another error is treating amide hydrolysis as easy; amides are the least reactive derivatives. Links to peptide bonds, Hofmann degradation, nylon and resonance.
Visualization of Amides
The amide group is like a carboxylic acid with N in place of OH; the C-N bond has partial double-bond character so the group is planar. The interactive lesson shows this as a live animation or chart.
Worked example and use case
Nylon and proteins both contain repeating amide links, which give these polymers their strength and rigidity.
Frequently asked questions about Amides
What is Amides?
Compounds with carbonyl bonded to nitrogen, stabilized by resonance and found in proteins.
Is Amides a beginner, intermediate or advanced topic?
Amides is a intermediate topic in Organic Chemistry. It builds on the vocabulary of beginner topics in this area.
What should I learn before Amides?
Study these earlier topics in Organic Chemistry first: Saponification, Soaps and Detergents, Acid Chlorides and Anhydrides.
What comes after Amides?
The next topics in Organic Chemistry are Amines and Basicity of Amines.
Can I practise Amides with quizzes?
Yes. The interactive lesson includes a self-check question on Amides, and the Organic Chemistry quiz draws on every topic in this area.
Where Amides fits in Organic Chemistry
Amides is topic 87 of 148 in Organic Chemistry.