Organic Chemistry Study Guides

Concise study guides, each built around a single question. Read the guide, look at the structures, then go practice — every page links straight into matching interactive problems.

Guides marked Early version have complete text with a few figures still being redrawn — polish lands weekly.

General Chemistry Foundations

• Review: Modeling Atoms and MoleculesEarly version What different models of atoms and molecules will you use to understand organic chemistry?
• Review: Lewis StructuresEarly version How do you draw and read Lewis structures?
• Review: Periodic TrendsEarly version How are periodic trends of elements/atoms relevant in molecules?
• Review: Chemical ReactionsEarly version What features of chemical reactions are important?
• Review: Acid–Base ReactionsEarly version Why does acid–base chemistry matter in organic chemistry?

Structure and Properties

• Drawing Organic MoleculesEarly version How do chemists communicate with each other about organic molecules?
• Structure and BondingEarly version How do atoms come together to form molecules?
• Functional GroupsEarly version How do organic chemists categorize the common groupings of atoms within molecules?
• IUPAC NomenclatureEarly version How do organic chemists name molecules unambiguously?
• Delocalization and ResonanceEarly version How do we approximate the sharing of electrons between more than two atoms?
• Conformational AnalysisEarly version What is the actual 3D nature of organic molecules? Are they static or flexible?
• Isomers and Stereochemistry What is the relationship between two molecules that share a formula? Chirality, enantiomers vs diastereomers, meso compounds, CIP rules, R/S and E/Z — with live examples from our problem bank.
• AromaticityEarly version Why do the stabilities of cyclic π-conjugated systems differ from linear ones?

Acidity and Reactivity

• pKa and Acid–Base Chemistry How do we evaluate the acidity and basicity of molecules? Conjugate pairs, predicting equilibria, and the six factors that control acidity.
• Chemical Reactions: Why and HowEarly version Why and how do molecules react with each other?

Spectroscopy and Structure Determination

• Mass SpectrometryEarly version How do we measure the mass of molecules?
• Infrared SpectroscopyEarly version How can we use the stretching and bending of bonds to determine functional groups?
• Proton NMR SpectroscopyEarly version How can we gain more information about the arrangement of H atoms in a molecule?
• Carbon-13 NMR SpectroscopyEarly version How can we gain more information about the arrangement of C atoms in a molecule?

Reactions and Mechanisms

• Aliphatic (sp³) Substitution ReactionsEarly version How do substitution reactions take place at sp³ atoms?
• Aliphatic (sp³) Elimination ReactionsEarly version What happens if the nucleophile attacks a H beta to the leaving group?
• Electrophilic Addition to AlkenesEarly version How do C=C bonds react?
• Electrophilic Aromatic Substitution (EAS) How do aromatic rings react with electrophiles? The five classic reactions, the arenium ion mechanism, directing effects, and Friedel-Crafts pitfalls.
• Nucleophilic Aromatic Substitution and DiazoniumsEarly version How do C=C bonds in aromatic rings react with nucleophiles?
• Nucleophilic Addition to CarbonylsEarly version How do different types of nucleophiles react with carbonyls?
• Nucleophilic Substitution at CarbonylsEarly version What happens in tetrahedral intermediates that have potential leaving groups?
• Keto-Enol TautomerizationEarly version What is the deal with carbonyls and their enol forms?
• Enols and Enolates as NucleophilesEarly version What do reactions using enols and enolates as nucleophiles look like?
• Olefination with Stabilized Carbanion NucleophilesEarly version How can we make alkenes from carbonyls?
• Radical ReactionsEarly version How do reactions involving free radicals work?
• Transition Metal ChemistryEarly version How do transition metal-catalyzed reactions work?

Pericyclic reactions are on the way. Want a topic prioritized — or spotted something to fix? Let us know.