The Organic Chemistry textbook

25 chapters, 123 sections. Every section below is a page you can read on its own.

Foundations

1. Atomic structure
2. Orbitals
3. Hybridization
4. Bonding
5. Electronegativity
6. Formal charge
7. Lewis structures
8. Molecular geometry
9. Bond polarity
10. Functional groups

Drawing Molecules & Moving Electrons

1. Skeletal structures
2. Curved arrows
3. Resonance

IUPAC Nomenclature

1. The parent chain
2. Substituents & locants
3. Functional group priority
4. Rings & unsaturation

Acids & Bases

1. Brønsted acids/bases
2. Conjugate acids/bases
3. pKa
4. Factors affecting acidity
5. Lewis acids/bases

Alkanes & Conformations

1. Newman projections
2. Cyclohexanes
3. Axial/equatorial
4. Ring flips
5. Conformational analysis

Stereochemistry

1. Chirality
2. Stereocenters
3. R/S configuration
4. Enantiomers
5. Diastereomers
6. Meso compounds
7. Fischer projections
8. Cis/trans and E/Z
9. Prochirality: which hydrogens are the same?

How Reactions Happen

1. Nucleophiles
2. Electrophiles
3. Electron-rich vs. electron-poor atoms
4. Leaving groups
5. Energy diagrams & the Hammond postulate
6. Carbocations
7. Radical halogenation

Substitution & Elimination

1. SN2
2. SN1
3. E2
4. E1
5. Substrate & solvent effects

Alkenes & Alkynes

1. Alkene structure
2. Addition reactions
3. Markovnikov / anti-Markovnikov
4. Oxidative cleavage & dihydroxylation
5. Carbenes & cyclopropanation
6. Catalytic hydrogenation
7. Alkynes

IR & Mass Spectrometry

1. IR
2. Mass spectrometry

Conjugation & Pericyclic Reactions

1. Conjugated systems
2. 1,2- vs 1,4-addition
3. Kinetic vs thermodynamic control
4. The Diels–Alder reaction
5. UV-Vis spectroscopy
6. Electrocyclic & sigmatropic reactions

Aromatic Chemistry

1. Aromaticity
2. Electrophilic aromatic substitution
3. Ortho/meta/para directing effects

Alcohols, Ethers & Related Chemistry

1. Alcohol reactions
2. Ether chemistry
3. Epoxides

Organometallic Bonding & Grignard Reagents

1. Why C–metal means nucleophilic carbon
2. Grignard reagents

Carbonyl Chemistry

1. Aldehydes & ketones
2. Nucleophilic addition
3. Hydrates & cyanohydrins
4. Acetals & hemiacetals
5. Imines and enamines
6. The Wittig reaction
7. Oxidizing an aldehyde

Oxidation & Reduction

1. Oxidation levels in organic chemistry
2. Oxidizing alcohols
3. Reducing carbonyls

Carboxylic Acids & Derivatives

1. Carboxylic acids
2. Esters & amides
3. Nucleophilic acyl substitution
4. Acid chlorides & anhydrides
5. Nitriles
6. Baeyer–Villiger oxidation

Organolithiums, Cuprates & Cross-Coupling

1. Organolithiums and acetylides
2. Cuprates and conjugate addition
3. Palladium cross-coupling

Enolate Chemistry

1. Alpha hydrogens & enolates
2. Aldol reactions
3. Claisen reactions
4. Alpha halogenation & the haloform reaction
5. Kinetic & thermodynamic enolates
6. Malonic and acetoacetic ester
7. Michael and Robinson

Amines

1. Structure & basicity
2. Amine reactions
3. Making amines
4. Hofmann elimination

Aromatic Follow-Through

1. SNAr and benzyne
2. Benzylic reactivity
3. Phenols
4. Birch reduction
5. Diazonium salts and Sandmeyer

NMR Spectroscopy

1. ¹H NMR
2. ¹³C NMR

Synthesis & Retrosynthesis

1. Thinking backwards
2. Making carbon–carbon bonds
3. Functional group interconversion
4. Protecting groups
5. Planning a multistep route

Biomolecules

1. Carbohydrates
2. Amino acids
3. Peptides and proteins
4. Lipids
5. Nucleic acids

Polymers

1. What a polymer is
2. Addition polymers
3. Condensation polymers
4. Structure and properties
5. Designing and unmaking a polymer