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Chemistry of Alcohols, Glycols, Thiols, Ethers, Epoxides, and Sulfides
- Oxidation and reduction
- Oxidation to aldehydes, ketones, and carboxylic acids
- Group equivalence
- Thiol oxidation
- Williamson synthesis
- Ethers from alkene addition
Chemistry of Ethers, Epoxides, and Sulfides
- Synthesis of epoxides
- Cleavage of ethers
- Nucleophilic substitution of epoxides
- Glycol cleavage
- Sulfonium salts
- Neighbouring–group participation
Dienes, Allylic, and Benzylic Reactivity
- Allenes (structure and stereochemistry)
- Conjugated dienes (1,3-dienes)
- Resonance & MO representation of conjugated π orbitals
- Addition of hydrogen halides to conjugated dienes
- Spectroscopy of benzene derivatives
- Allylic and benzylic reactivity
Aromaticity and Electrophilic Aromatic Substitution
- Benzene, aromaticity, and other aromatic systems
- Nomenclature of benzene derivatives
- Other aromatic systems
- Electron donating and withdrawing groups
- Inductive vs. resonance effects; effects of substituents
- General mechanism of electrophilic aromatic substitution
- Halogenation, Nitration, Sulfonation, Friedel-Crafts Alkylation and Acylation
Electrophilic and Nucleophilic Aromatic Substitution
- Directing and activating effects in electrophilic aromatic substitution
- Use of electrophilic aromatic substitution in synthesis
- Unreactivity of aryl and vinylic halides
- Nucleophilic substitution of aryl halides (benzyne and addition-elimination mechanisms)
Aldehydes and Ketones - Carbonyl Addition
- Structure and reactivity of the C=O group
- Irreversible additions to aldehydes and ketones: Grignard reagents, NaBH4, and LiAlH4
Aldehydes and Ketones - Carbonyl Addition
- Reversible addition reactions of aldehydes and ketones: hydration, hemiacetals, acetals
- Use of acetals as protecting groups
- Formation and hydrolysis of imines and enamines
- The Wittig Alkene Synthesis
- Reduction of aldehydes and ketones to alkanes
Chemistry of Carboxylic Acids and their Derivatives
- Acidity of carboxylic acids
- Preparations of carboxylic acids
- General mechanism for interconversion of carboxylic acid derivatives
- Introduction to the Grid of Carbonyl Love
- Converting between carboxylic acids, acid chlorides, esters, and amides
- Hydrolysis of nitriles
Chemistry of Carboxylic Acids and their Derivatives
- Reduction of esters, carboxylic acids, amides, and nitriles with LiAlH4
- Alternative methods for the synthesis and hydrolysis of esters
- Relative reactivity of carboxylic acid derivatives
- Reaction of carboxylic acids and derivatives with hydride reagents, *Grignard reagents, and organolithium reagents
- Preparation of ketones from carboxylic acids and derivatives
- Reduction of esters to aldehydes (DIBAL)
- Oxidizing ketones: The Baeyer-Villiger Oxidation
- The complete Grid of Carbonyl Love
Introduction to carbohydrates, peptides, and proteins
- Structure, nomenclature, and stereochemistry of carbohydrates
- Formation of acetals, disaccharides, and polysaccharides
- Structure of alkyl glucosides: the anomeric effect
- Structure and synthesis of amino acids
- The peptide bond and synthesis of peptides
- Solid-phase peptide synthesis
Enols, Enolates, and α,β-Unsaturated Compounds
- Acidity of C=O compounds (enolate formation)
- Tautomerization of C=O compounds (enol formation)
- Deuteration and racemization of α-carbons
- Halogenation under acidic and basic conditions; the haloform reaction
- Introduction to the aldol reaction: addition and condensation
- Intramolecular and crossed aldol condensations
Enols, Enolates, and α,β-Unsaturated Compounds
- Claisen and Dieckmann condensations
- Hydrolysis and decarboxylation of β-keto esters
- Alkylation of moderately basic enolate ions
- Synthesis using aldol and Claisen reactions
- Controlling the enolization of C=O compounds: Using lithium enolates
- Alkylation of lithium enolates
Enols, Enolates, and α,β-Unsaturated Compounds
- Crossed aldol and Claisen reactions
- Formation of enolates from α-bromo esters
- Introduction to α,β-unsaturated compounds: Nucleophilic addition
- Addition of dialkyl cuprates
- Kinetic (1,2) vs. thermodynamic (1,4) addition
- The Michael reaction
Enols, Enolates, and α,β-Unsaturated Compounds
- Robinson annulation
- A systematic approach to organic synthesis: Retrosynthetic analysis
- Organic synthesis using aldol, Claisen, Michael, and related reactions
Chemistry of Amines
- Nomenclature, structure, and acid/base reactions of amines
- Preparation of primary amines: reduction of azides and nitriles
- Preparation of secondary and tertiary amines: reductive amination
- Amines from conjugate addition; amines from nitrile enolates
Chemistry of Amines
- Mannich reaction in the synthesis of natural amines
- 1,2-rearrangements to nitrogen: Beckmann, Hofmann, and Curtius rearrangements
- Synthesis and reactivity of aromatic amines
- Preparation and reactivity of aryl diazonium salts
- Using aryl diazonium salts in synthesis
Diels-Alder and Pericyclic Reactions
- Introduction to pericyclic reactions
- Molecular orbitals of conjugated π-electron systems
- Diels–Alder reaction
- Synthesis using the Diels-Alder reaction
Pericyclic Reactions
- Other cycloaddition reactions (incl. photochemical 2+2 cycloadditions)
- Electrocyclic reactions of conjugated dienes and trienes (thermal and photochemical)
- Sigmatropic reactions ([1.3], [1,5], [3,3] rearrangements)
- Summary of pericyclic selection rules
The Organic Chemistry of Life
- Key cofactors: Thiamine, NADH, and lipoamide
- Cholesterol biosynthesis and the role of statins
- Fatty-acid biosynthesis
- Polyketide biosynthesis
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