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Structure, Bonding, and Representations

Drawing, bonding, charge, resonance, orbital, and functional-group language for organic molecules. Topics: Organic Representations, Bonding and Hybridization, Formal Charge and Resonance, Functional Groups.

Acids, Bases, and Electronic Effects

Reusable pKa, nucleophile/electrophile, induction, resonance, and noncovalent reasoning. Topics: Acid-Base Reasoning, Electronic Effects, Nucleophiles and Electrophiles, Intermolecular Forces.

Isomerism, Conformation, and Stereochemistry

Constitutional isomers, conformations, cyclohexanes, chirality, stereochemical labels, and stereoisomer relationships. Topics: Constitutional Isomerism and Nomenclature, Conformational Analysis, Configuration Labels, Stereoisomer Relationships.

Mechanisms, Energy, and Reaction Strategy

Curved-arrow electron flow, intermediates, energy profiles, rate laws, selectivity, and reaction-category reasoning. Topics: Curved-Arrow Mechanisms, Reaction Energy and Rates, Selectivity and Rearrangements, Reaction Strategy.

Alkanes, Cycloalkanes, and Radical Chemistry

Saturated hydrocarbons, strain, combustion, radical halogenation, and radical mechanisms. Topics: Alkanes and Cycloalkanes, Radical Reactions.

Alkenes and Alkynes

Pi-bond structure, addition selectivity, synthesis, reduction, oxidation, and cleavage. Topics: Alkene Addition Reactions, Alkyne Reactions, Pi-Bond Synthesis and Strategy.

Substitution and Elimination

Alkyl halide reactions, SN1/SN2/E1/E2 mechanisms, substrate/reagent/solvent effects, and competition. Topics: SN2 Reactions, SN1 Reactions, E1 and E2 Reactions, Substitution-Elimination Competition.

Spectroscopy and Structure Determination

Mass spectrometry, IR, NMR, UV-visible patterns, and combined structure-elucidation problems. Topics: Mass Spectrometry, Infrared Spectroscopy, NMR Spectroscopy, Combined Structure Determination.

Conjugation and Aromaticity

Conjugated systems, diene reactivity, aromatic criteria, antiaromaticity, and heteroaromatic electron counting. Topics: Conjugated Systems, Aromaticity.

Aromatic Reactions

Electrophilic and nucleophilic aromatic substitution, directing effects, benzylic chemistry, and aromatic synthesis. Topics: Electrophilic Aromatic Substitution, Aromatic Synthesis.

Alcohols, Phenols, Ethers, Epoxides, and Sulfur Compounds

Oxygen and sulfur functional groups, oxidation/reduction, substitution, protection, and epoxide chemistry. Topics: Alcohols and Phenols, Oxidation and Reduction, Ethers and Epoxides, Sulfur Compounds and Protecting Groups.

Aldehydes and Ketones: Carbonyl Addition

Carbonyl polarity, aldehyde and ketone nomenclature, nucleophilic addition, hydride, organometallic, and derivative-forming reactions. Topics: Carbonyl Structure and Reactivity, Aldehyde and Ketone Additions.

Carboxylic Acids and Derivatives: Acyl Substitution

Carboxylic acids, nitriles, acid derivatives, reactivity order, interconversion, reductions, and addition-elimination mechanisms. Topics: Carboxylic Acids and Nitriles, Nucleophilic Acyl Substitution.

Enols, Enolates, and Condensations

Alpha acidity, enolate formation, alpha substitution, aldol and Claisen chemistry, conjugate addition, and carbon-carbon bond synthesis. Topics: Enols and Enolates, Aldol Reactions, Claisen and Related Condensations, Conjugate Addition.

Amines and Heterocycles

Nitrogen functional groups, amine basicity, amine synthesis and reactions, diazonium chemistry, and heterocycle patterns. Topics: Amine Properties and Synthesis, Amine Reactions, Heterocycles.

Multistep Synthesis and Retrosynthesis

Multistep synthesis planning, reagent choice, functional-group interconversion, protecting groups, route comparison, and strategy. Topics: Multistep Synthesis and Retrosynthesis.

Bioorganic Molecules and Materials

Bioorganic molecules and materials: the structures and characteristic reactions of carbohydrates, amino acids, peptides and proteins, lipids, and nucleic acids; the orbital-symmetry treatment of pericyclic reactions (cycloadditions, electrocyclizations, and sigmatropic rearrangements) that builds on the conjugation and Diels-Alder work; and the formation, classification, and structure-property relationships of synthetic polymers. Topics: Biomolecules, Pericyclic Reactions, Polymers and Materials.