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



Lesson I.17. Stereochemistry I: Chirality and Optical Activity          

Lesson I.18. Stereochemistry II: Cahn-Ingold-Prelog Rules and Assigning R- and S- Labels of Configuration

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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Part III: Alkenes and Alkynes

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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)

These Lessons are not developed into full lessons with videos, but the textbook can be downloaded at the link above

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