Chapter 1: Atoms and Molecules, Orbitals and Bonding
1.1: Atoms and Atomic Orbitals
1.2: Covalent Bonds and Lewis Structures
1.3: Formal Charge, Resonance Structure, Nucleophile-Electrophile Reactions
1.4: More Examples on Lesson 3
1.5: Hydrogen – Molecular Orbitals
1.6: Bond Strength
Chapter 2: Functional Families and Nomenclature
2.1: Drawing Skeletal Structures. Naming Prefixes. Nomenclature of Alkanes, Alkenes, Alkynes
2.3: More on Double and Triple Bonds in Rings
2.4: Heats of Formation, Relative Acidity, Degrees of Unsaturation of Alkanes, Alkenes, Alkynes
2.5: IUPAC Nomenclature of Organic Substituents
2.6: Geometric Isomers, Cis/Trans/E/Z Naming of Alkenes
2.7: Further Nomenclature Rules
2.8: Nomenclature and Properties of Carboxylic Acids, Alcohols, Thiols, Ethers, Thioethers, Esters
2.9: Nomenclature and Properties of Amines, Amides, and Heterocyclic Compounds
2.10: Nomenclature and Properties of Aldehydes, Ketones, and Related Compounds
2.11: Nomenclature and Properties of Anhydrides, Acyl Halides (Eg. Acid Chlorides), Nitriles
2.12: Putting it All Together – Trickier Examples
2.13: Special Topics – Crown Ethers
Chapter 3: Stereochemistry
3.1: Isomers and Sterochemistry Intro
3.2: Chirality
3.3: Newman Projections
3.4: Fisher Projections
3.5: Chair Conformations
3.6: Types of Stereochemistry – Enantiomers
3.7: Physical and Chemical Properties of Enantiomers
3.8: Interconversion of Enantiomers by Rotation about a Single Bond (gauche – Butance)
3.9: Types of Stereochemistry – Diastereomers and Molecules with more than one Stereogenic Atom
3.10: Physical and Chemical Properties of Diastereomers
3.11: Using Absolute Configuration (R/S)
3.12: Stereochemistry in Rings
3.13: Examples – Putting It All Together
3.14: Special Topic – Chirality Without “Four Different Groups Attached to One Carbon”
3.15: Stereochemistry in the Real World, Thalidomide and its Consequences
Chapter 4: Rings
4.1: Rings and Strain
4.2: Evaluation of Strain Energy
4.3: Stereochemistry of Cyclohexane – Conformational Analysis
4.4: Monosubstituted Cyclohexanes
4.5: Disubstituted Ring Compounds
4.6: Polycyclic Systems
4.7: Special Topic – Adamantanes in Materials and Biology
Chapter 5: Substitution and Elimination Reactions – SN1, SN2, E1, E2
5.1: Preview
5.2: Reivew of Lewis Acids and Bases
5.3: Reactions of Alkyl Halides – Substitution Reaction
5.4: Substitution, Nucleophilic, Bimolecular – SN2 Reaction
5.5: SN2 Reaction in Biochemistry
5.6: Substitution, Nucleophilic, Unimolecular – SN1 Reaction
5.7: Summary and Overview of SN1 and SN2
5.8: Unimolecular Elimination – E1 Reaction
5.9: Bimolecular Elimination – E2
5.10: Organic Synthesis with these Reactions
5.11: More Examples!
Chapter 6: Equilibria
6.1: Preview
6.2: Equilibrium
6.3: Entropy in Organic Reactions
6.4: Rates of Chemical Reactions
6.5: Rate Constant
6.6: Energy Barriers in Chemical Reactions – Transition State and Activation Energy
6.7: Reaction Mechanism
6.8: Hammond Postulate – Thermodynamics vs Kinetics
6.9: Enzymes and Reaction Rates
6.10: Summary
Chapter 7: Alkene Addition
7.1: Preview
7.2: Mechanism of Addition of Hydrogen Halides to Alkenes
7.3: Effects of Resonance on Regiochemistry
7.4: Brief Review of Resonance
7.5: Resonance and Carbocation Stability
7.6: Inductive Effects on Addition Reactions
7.7: HX Addition Reactions – Hydration
7.8: Dimerization and Polymerization of Alkenes
7.9: Hydroboration
7.10: Hydroboration in Synthesis – Alcohol Formation
7.11: Addition of H2 and X2 Reagents
7.12: Hydration through Mercury Compounds – Oxymercuration
7.13: Other Addition Reactions with Three-Membered Rings – Oxiranes and Cylopropanes
7.14: Dipolar Addition Reactions – Ozonolysis and the Synthesis of Carbonyl
7.15: More Examples!
7.16: Special Topics – Rearrangements in Biological Processes
Chapter 8: Addition Reactions of Alkynes
8.1: HX Addition to Alkynes
8.2: Addition of X2 Reagents to Alkynes
8.3: Hydration of Alkynes
8.4: Hydroboration of Alkynes
8.5: Hydrogenation of Alkynes – Alkene Synthesis through syn Hydrogenation
8.6: Reduction by Sodium in Ammonia – Alkene Synthesis through anti Hydrogenation
Chapter 9: Radical Reactions
9.1: Preview
9.2: Formation and Simple Reactions of Radicals
9.3: Structure and Stability of Radicals
9.4: Radical Addition to Alkenes
9.5: Other Radical Addition Reactions
9.6: Radical-Initiated Addition of HBr to Alkynes
9.7: Photohalogenation
9.8: Allylic Halogenation – Synthetically Useful Reactions
9.9: Rearrangements (and Nonrearrangements) of Radicals
9.10: Special Topic – Do Free Radicals in the Body Age Us?
Link to Textbook: Organic Chemistry, 4th Edition by Jones and Fleming
Chapter 1: Dienes and the Allyl System
1.1: Preview
1.2: Allenes
1.3: Related Systems – Ketenes and Cumulenes
1.4: Allenes as Intermediates in the Isomerization of Alkynes
1.5: Conjugated Dienes
1.6: Physical Consequences of Conjugation
1.7: Molecular Orbitals and Ultraviolet Spectroscopy
1.8: Polyenes and Vision
1.9: Conjugated Systems
1.10: Chemical Consequences of Conjugation – Addition Reactions of Conjugated Dienes
1.11: Thermodynamic and Kinetic Control of Addition Reactions to Dienes
1.12: Allyl System – Three Overlapping 2p Orbitals
1.13: Diels-Alder Reaction of Conjugated Dienes
1.14: Special Topic – Biosynthesis of Terpenes
1.15: Summary
Chapter 2: Conjugation and Aromaticity
2.1: Preview
2.2: Benzene Structure
2.3: Resonance Picture of Benzene
2.4: Molecular Orbital Picture of Benzene
2.5: Quantitative Evaluations of Resonance Stabilization in Benzene
2.6: Generalization of Aromaticity – Huckel’s 4n + 2 Rules
2.7: Substituted Benzenes
2.8: Physical Properties of Substituted Benzenes
2.9: Heterobenzenes and other Heterocyclic Aromation Compounds
2.10: Polynuclear Aromatic Compounds
2.11: Chemistry of Benzene
2.12: Benzyl Group and Its Reactivity
2.13: Special Topic – Bio-Downside, the Mechanism of Carcinogensis by Polycyclic Aromatic Compounds
2.14: Summary
Chapter 3: Substitution Reactions of Aromatic Compounds
3.1: Preview
3.2: Hydrogenation of Aromatic Compounds
3.3: Diels-Alder Reactions
3.4: Substitution Reactions of Aromatic Compounds
3.5: Carbon-Carbon Bond Formation – Friedel-Crafts Alkylations
3.6: Friedel-Crafts Acylation
3.7: Synthetic Reactions We Can Do So Far
3.8: Electrophilic Aromatic Substituion of Heteroaromatic Compounds
3.9: Disubstituted Benzenes – Ortho, Meta, Para Substitution
3.10: Inductive Effects in Aromatic Substituion
3.11: Synthesis of Polysubstituted Benzenes
3.12: Nucleophilic Aromatic Substitution
3.13: Special Topic – Stable Carbocations in “Superacid”
3.14: Special Topic – Benzyne
3.15: Special Topic – Biological Synthesis of Aromatic Rings, Phenylalanine
3.16: Summary
Chapter 4: Spectroscopy
4.1: Preview
4.2: Chromatography
4.3: Mass Spectrometry (MS)
4.4: 1H Nuclear Magnetic Resonance Spectroscopy (NMR)
4.5: NMR Measurements
4.6: 13C NMR Spectroscopy
4.7: How to Use Spectroscopy to Determine Structures
4.8: Special Topic – Dynamics NMR
4.9: More Examples
4.10: Summary
Chapter 5: Carbonyl Chemistry – Addition Reactions
5.1: Preview
5.2: Structure of the Carbon-Oxygen Double Bond
5.3: Nomenclature of Carbonyl Compounds
5.4: Physical Properties of Carbonyl Compounds
5.5: Reactions of Carbonyl Compounds – Simple Reversible Additions
5.6: Equilibrium in Addition Reactions
5.7: Other Addition Reactions – Additions of Cyanide and Bisulfite
5.8: Additional Reactions Followed by Water Loss – Acetal Formation
5.9: Protecting Groups in Synthesis
5.10: Addition Reactions of Nitrogen Base – Imine and Enamine Formation
5.11: Organometallic Reagents
5.12: Irreversible Addition Reactions – A General Synthesis of Alcohols
5.13: Oxidation of Alcohols to Carbonyl Compounds
5.14: Retrosynthetic Alcohol Synthesis
5.15: Oxidation of Thiols and Other Sulfur Compounds
5.16: Witting Reaction
5.17: Special Topic – Biological Oxidation
5.18: More Examples
5.19: Summary
Chapter 6: Carboxylic Acids
6.1: Preview
6.2: Infrared and NMR Spectra of Carboxylic Acids
6.3: Acidity and Basicity of Carboxylic Acids
6.4: Synthesis of Carboxylic Acids
6.5: Reactions of Carboxylic Acids
6.6: Special Topics – Fatty Acids
6.7: Extra Problems
6.8: Summary
Chapter 7: Derivatives of Carboxylic Acids – Acyl Compounds
7.1: Preview
7.2: Nomenclature
7.3: Physical Properties and Structures
7.4: Acidity and Basicity of Acyl Compounds
7.5: Special Characteristics
7.6: Reactions of Acid Chlorides – Synthesis of Acyl Compounds
7.7: Reactions of Anhydrides
7.8: Reaction of Esters
7.9: Reaction of Amides
7.10: Reactions of Nitriles
7.11: Special Topic – Other Synthetic Routes to Acid Derivatives
7.12: Special Topic – Thermal Elimination Reactions of Esters
7.13: Special Topic – A Family of Concerted Rearrangements of Acyl Compounds
7.14: Example Problems
7.15: Summary
Chapter 8: Carbonyl Chemistry – Reactions at the Alpha Position
8.1: Preview
8.2: Many Carbonyl Compounds are Weak Bronsted Acids
8.3: Racemization of Enols and Enolates
8.4: Halogenation in the Alpha Position
8.5: Alkylation in the Alpha Position
8.6: Addition of Carbonyl Compounds to the Alpha Position – The Alodol Condensation
8.7: Reactions Related to the Aldol Condensation
8.8: Addition of Acid Derivatives to the Alpha Position – Claisen Reaction
8.9: Special Topic – Forward and Reverse Claisen Condensation in Biology
8.10: Condensation Reactions in Combination
8.11: Special Topic – Alkylation of Dithianes
8.12: Special Topic – Amines in Condensation Reactions, the Mannich Reaction
8.13: Special Topic – Carbonyl Compounds without Alpha Hydrogens
8.14: Special Topic – Aldol Condensation in the Real World
8.15: Example Problems
8.16: Summary
Chapter 9: Reactions Controlled by Orbital Symmetry
9.1: Preview
9.2: Concerted Reactions
9.3: Electrocyclic Reactions
9.4: Cycloaddition Reactions
9.5: Sigmatropic Shift Reactions
9.6: Cope Rearrangement
9.7: A Molecule with Fluxional Structure
9.8: How to Work with Orbital Symmetry Problems
9.9: Examples
9.10: Summary
Chapter 10: Intramolecular Reactions and Neighboring Group Participation
10.1: Preview
10.2: Heteroatoms as Neighboring Groups
10.3: Neighboring Pi Systems
10.4: Single Bonds as Neighboring Groups
10.5: Coates’ Cation
10.6: Examples
10.7: Summary
Chapter 11: Carbohydrates
11.1: Preview
11.2: Nomenclature and Structure of Carbohydrates
11.3: Formation of Carbohydrates
11.4: Reactions of Carbohydrates
11.5: Fischer Determination of the Structure of D-Glucose (and 15 Other Aldohexoses)
11.6: Disaccharides and Polysaccharides
11.7: Examples
11.8: Summary
Chapter 12: Amino Acids and Polyamino Acids
12.1: Preview
12.2: Amino Acids
12.3: Reactions of Amino Acids
12.4: Peptide Chemistry
12.5: Nucleosides, Nucleotides, and Nucleic Acids
12.6: Examples
12.7: Summary
Link to Textbook: Organic Chemistry 5th edition by Maitland & Fleming