Organic Chemistry -Free Course
Rhett C. Smith, Ph.D.: Academic accessibility for all!
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Full Table of Contents
From "Organic Chemistry 1 Primer 2020" by Smith, Tennyson and Houjeiry. If you prefer a paper copy you can get them from Amazon: Amazon link for Organic 1 Primer or Amazon link for Organic 2 Primer.
Part I: Foundations
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The Basics: Structure and Representations
Lesson I.1. Coulombic Forces and Representation of Structure
Lesson I.2. Polarity, Dipole Moments and Formal Charge
Lesson I.3. Intermolecular Forces, Boiling Point/Melting Point and Ionic vs. Covalent
Lesson I.4. Nucleophiles, Electrophiles and Functional Groups
Lesson I.5. Arrow-Pushing Formalism
Lesson I.6. Hybridization, Sigma and Pi Bonds, Lone Pairs and Bond Geometry
Lesson I.7. Resonance and Delocalization Energy
Lesson I.8. Applying the Arrow-Pushing Formalism
Stability and Energy in Organic Chemistry
Lesson I.9. Definitions and Concepts related to Acids and Bases
Lesson I.10. Relating Structure to the Strength of an Acid or Base
Lesson I.11. Stability of Carbocations and Alkenes
Lesson I.12. Predicting Reaction Spontaneity and Direction of Equilibria
Lesson I.13. Reaction Coordinate Diagrams and Reaction Rate
Nomenclature and Conformations of Alkanes and Cycloalkanes
Lesson I.14. Nomenclature I: Alkanes, Alkyl Halides, Alcohols and Cycloalkanes
Lesson I.15. Isomerism and Conformational Analysis I: Linear Alkanes and Newman Projections
Lesson I.16. Conformational Analysis II: Cycloalkanes and the Chair Conformation of Cyclohexane
Stereochemistry
Lesson I.17. Stereochemistry I: Chirality and Optical Activity
Lesson I.19. Stereochemistry III: Fischer Projections
Lesson I.20. Stereochemistry IV: Enantiomers, Diastereomers and Meso Compounds
Part II: Substitution and Elimination
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Substitution and Elimination of Alkyl Halides
Lesson II.1. Tracking Stereocenters in Reactions
Lesson II.2. Nucleophilicity versus Basicity and Solvent Effects
Lesson II.3. The SN1 Reaction of Alkyl Halides
Lesson II.4. The SN2 Reaction of Alkyl Halides
Lesson II.5. Stereochemistry of Substitution Reactions
Lesson II.6. The E1 Reaction of Alkyl Halides
Lesson II.7. The E2 Reaction of Alkyl Halides
Lesson II.8. Stereoelectronic Effects in the E2 reaction
Lesson II.9. Factors Leading to Non-Zaitsev Products in the E2 Reaction
Lesson II.10. Competition Among Substitution and Elimination Reactions of RX: Predicting Pathways
Reactions of Alcohols, Ethers and Epoxides
Lesson II.11. Substitution and Elimination of Alcohols
Lesson II.12. Oxidation and Reduction: Definitions
Lesson II.13. Oxidation Reactions of Alcohols
Lesson II.14. Nomenclature and Acid Cleavage of Ethers
Lesson II.15. Ring-Opening of Epoxides: Steric/Electronic Effects on Major Product
Part III: Alkenes and Alkynes
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Nomenclature and Reactions of Alkenes
Lesson III.1. Alkene Nomenclature and the E-/Z- Convention
Lesson III.2. Properties of Alkenes and Hydrogenation of Alkenes
Lesson III.3. Electrophilic Addition to Alkenes and Carbocation Rearrangement Revisited
Lesson III.4. Introducing Addition to Alkenes
Lesson III.5. Hydrohalogenation and Hydration of Alkenes
Lesson III.6. Alkene Halogenation and Halohydrin Formation
Lesson III.7. Oxymercuration/Reduction of Alkenes
Lesson III.8. Epoxidation of Alkenes
Lesson III.9. Hydroboration/Oxidation of Alkenes
Lesson III.10. Reactions of Alkenes VI: Ozonolysis and Preparation of Vicinal Diols
Nomenclature and Reactions of Alkynes
Lesson III.11. Naming and Making Alkynes
Lesson III.12. Hydrohalogenation and Halogenation of Alkynes
Lesson III.13. Three Ways to Reduce Alkynes
Lesson III.14. Facile Constitutional Isomerism: Tautomerization
Lesson III.15. Preparing Carbonyls from Alkynes
Lesson III.16. Acetylide Anion Preparation and its use as a Nucleophile
Reactions Involving Radicals
Lesson III.17. Radicals I: Peroxide-Mediated Hydrobromination of Alkenes
Lesson III.18. Radicals II: Halogenation of Alkanes
Lesson III.19. Radicals III: Radical Polymerization of Alkenes
Part IV: Conjugated and Aromatic Molecules
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Pi Conjugation and Conjugated Dienes
Lesson IV.1. Pi Conjugation Stabilizes a Molecule
Lesson IV.2. Addition Reactions of Conjugated Dienes
Lesson IV.3. Diels-Alder Reaction
Aromaticity and Electrophilic Aromatic Substitution
Lesson IV.4. Aromaticity: A Highly Stabilizing Effect
Lesson IV.5. Aromaticity Effects on Acidity and Basicity
Lesson IV.6. Nomenclature of Monosubstituted Benzene Compounds
Lesson IV.7. Electrophilic Aromatic Substitution I: Friedel–Crafts Alkylation and Acylation
Lesson IV.8. Electrophilic Aromatic Substitution II: Nitration and Sulfonation of Benzene
Lesson IV.9. Electrophilic Aromatic Substitution III: Halogenation of Benzene
Lesson IV.10. Nomenclature of Polysubstituted Benzene Compounds
Lesson IV.11. Substituent Effects on the Rate of Electrophilic Aromatic Substitution
Lesson IV.12. Substituent Effects on the Regiochemistry of Electrophilic Aromatic Substitution
Lesson IV.13. More on the Directing Effects of Substituents in EAS
More Reactions involving Aromatic Molecules
Lesson IV.14. Oxidation and Reduction of Substituents on Benzene Rings
Lesson IV.15. Radical Halogenation of Allylic and Benzylic Compounds
Lesson IV.16. Nucleophilic Aromatic Substitution
Lesson IV.17. Formation and Reaction of Diazonium Salts
Part V: Organometallic Compounds and Metal Hydrides
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Introduction to Carbon Nucleophiles
Lesson V.1 Introduction to Organometallics, Metal Hydrides and Carbenes
Lesson V.2 Preparation of Organolithium, Grignard and Gilman Reagents
Lesson V.3 Reaction of Organometallics/Metal Hydrides with RX and Epoxides
Pd-Catalyzed Coupling and Olefin Metathesis
Lesson V.4 Palladium-Catalyzed C–C Bond-Forming Reactions
Lesson V.5 Introduction to Alkene Metathesis
Lesson V.6 Applications of Alkene Metathesis
Part VI: Carbonyls
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Introduction to Carbonyls
Lesson VI.1. Nomenclature of Carbonyls
Lesson VI.2. Review: Preparation of Carbonyls from Alcohols, Alkynes and Alkenes
Lesson VI.3. Classifying Reactions of Carbonyls
Lesson VI.4. Relative Rates of Nucleophilic Attack on Carbonyl Functional Groups
Reactions of Aldehydes and Ketones
Lesson VI.5. Addition of Organometallics/Metal Hydrides to Aldehydes/Ketones
Lesson VI.6. Addition of Water or Alcohols to Aldehydes/Ketones
Lesson VI.7. Addition of Amine Derivatives to Aldehydes/Ketones
Lesson VI.8. The Wittig Reaction
Reactions of Carboxylic Acid Derivatives and Nitriles
Lesson VI.9. Nucleophilic Acyl Substitution of Acid Chlorides and Anhydrides
Lesson VI.10. SNAc of Carboxylic Acids to form Acid Chlorides
Lesson VI.11. SNAc Reaction of Oxygen Nucleophiles with Carboxylic Acids and Esters
Lesson VI.12. Amide Formation, Amide Hydrolysis and the Gabriel Synthesis
Lesson VI.13. Reaction of Carboxylic Acid Derivatives with H and C Nucleophiles
Lesson VI.14. Preparation and Reaction of Nitriles
Enolates and alpha,beta-Unstaurated Carbonyls
Lesson VI.15. Preparation of Enolates and Alkylation
Lesson VI.16. Alpha-Halogenation and Haloform Reactions
Lesson VI.17. Aldol Addition and Condensation
Lesson VI.18. Claisen Condensation
Lesson VI.19. Decarboxylation and Synthetic Applications
Lesson VI.20. Addition of Nucleophiles to alpha,beta-Unsaturated Carbonyls
Part VII: Determining the Structure of Organic Compounds
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Ultraviolet-Visible Spectroscopy
Lesson VII.1. Interaction of Ultraviolet and Visible Light with Molecules
Lesson VII.2. UV–Visible Spectroscopy
Infrared Spectroscopy
Lesson VII.3. Interaction of Infrared Light with Molecules
Lesson VII.4. Infrared Spectroscopy
Nuclear Magnetic Resonance Spectrometry
Lesson VII.5. Introduction to Nuclear Magnetic Resonance
Lesson VII.6. Carbon-13 Nuclear Magnetic Resonance Spectrometry
Lesson VII.7. Proton Nuclear Magnetic Resonance Spectrometry
Mass Spectrometry Click here to download the text (.PDF)
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Lesson VII.8. Introduction to Mass Spectrometry
Lesson VII.9. Introduction to Fragmentation Mechanisms
Lesson VII.10. Fragmentation of Alkanes
Lesson VII.11. Fragmentation of Heteroatom-Containing Aliphatics
Lesson VII.12. Fragmentation of Carbonyl-Containing Molecules
Lesson VII.13. Fragmentation of Arenes
Lesson VII.14. Fragmentation of Alkenes
Lesson VII.15. Fragmentation of Other Unsaturated Molecules