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
• Indtroduction 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

Organic Chemistry, Clayden, Greeves, Warren, ISBN 978-3-642-34715-3

Organic chemistry: structure and function. Vollhardt, K. Peter C. — 5th ed. / K. Peter C. Vollhardt, Neil E. Schore. ISBN 0-7167-9949-9