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Ch. 2 - Molecular RepresentationsWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Ch. 26 - Transition Metals
Intermolecular Forces
How To Determine Solubility
Functional Groups
Additional Guides
London Dispersion Force
Van Der Waals
Johnny Betancourt

Amides are carboxylic acid derivatives. The hydroxyl group is replaced by ammonia or a primary or secondary amine. 

Lewis structure:Amide Lewis structuresAmide Lewis Structures

Amides get their degrees based on how many carbon atoms are directly attached to the nitrogen atom. From left to right, the image above shows primary, secondary, and tertiary amides.

Hybridization and resonance:

Two truths and a lie: 

1. the oxygen is sp2-hybridized

2. the carbonyl carbon is sp2-hybridized

3. the nitrogen is sp3-hybridized. 

Which one is the lie? The nitrogen is actually NOT sp3. Its electron density is actually distributed with the carbonyl carbon and the oxygen, so it’s actually sp2. Let me prove it to you with a resonance structure:

Amide resonanceAmide resonance

Pro-tip: whenever an atom can resonate, it will (at least in Orgo 1)! Remember that a molecule with delocalized electron density is more stable, and that more stability means a lower energy state.

Amine vs amide:

What’s the difference? What’s the secret sauce that allows us to distinguish between the two? It's just a carbonyl.

Amide vs amineAmide vs amine

The molecule on the left is an amide, and the molecule on the right is an amine. The amide has an oxygen double-bonded to the carbon directly attached to the nitrogen, but the amine does not. That carbonyl is what makes this nitrogen compound an amide.

Where are amides found?

Amides are formed in biological systems when amino acids bond to form peptides, which in turn form polypeptides and proteins. They’re also found in local anesthetics like lidocaine.

Hope this quick overview of amides helped! Good luck studying!

Johnny Betancourt

Johnny got his start tutoring Organic in 2006 when he was a Teaching Assistant. He graduated in Chemistry from FIU and finished up his UF Doctor of Pharmacy last year. He now enjoys helping thousands of students crush mechanisms, while moonlighting as a clinical pharmacist on weekends.