Section 1: Laying the Foundations
Basics 1: Structures of Organic Compounds
Habit 1: Always Draw Structures with Realistic Geometry
Basics 2: Functional Groups and "R" Groups
Basics 3: Naming Organic Compounds
Practice 1: Drawing Structures from Chemical Names
Basics 4: Isomerism in Organic Chemistry - Constitutional Isomers
Practice 2: Constitutional Isomers and Chemical Names
Habit 2: Identifying When a Formula is Possible
Practice 3: Double Bond Equivalents
Common Error 1: Formulae, Functional Groups and Double Bond Equivalents
Habit 3: Ignore What Doesn't Change
Basics 5: Electronegativity, Bond Polarisation and Inductive Effects
Practice 4: Bond Polarisation and Electronegativity
Basics 6: Bonding in Organic Compounds
Practice 5: Hybridisation
Basics 7: Bonding and Antibonding Orbitals
Basics 8: Introduction to Curly Arrows
Fundamental Reaction Type 1: Nucleophilic Substitution at Saturated Carbon
Practice 6: Electronegativity in Context
Fundamental Reaction Type 2: Elimination Reactions
Section 2: Building on the Foundations
Basics 9: Breaking Bonds – Linking Curly Arrows and Molecular Orbitals
Common Error 2: Curly Arrows
Basics 10: Conjugation and Resonance
Basics 11: Thermodynamic Definitions
Basics 12: Bond Dissociation Energy
Basics 13: Calculating Enthalpy of Reaction from Bond Dissociation Energies
Perspective 1: A Closer Look at Bond Dissociation Energies
Practice 7: Calculating Enthalpy of Reaction from Bond Dissociation Energy
Basics 14: Energetics and Reaction Profiles
Basics 15: How Fast Are Reactions?
Basics 16: Introduction to Carbocations, Carbanions and Free-Radicals
Basics 17: Carbocations 2 - More Factors Affecting Stability
Basics 18: Carbanions 2 - Stability and pKa
Perspective 2: A Scale for Carbocation Stability
Common Error 3: Methyl Groups are Electron-Releasing
Practice 8: Drawing Resonance Forms for Carbocations and Carbanions
Common Error 4: Resonance
Basics 19: The Hammond Postulate
Basics 20: Conjugation and Stability - The Evidence
Common Error 5: Carbocations and Carbanions
Basics 21: Reactivity of Conjugated Systems
Basics 22: Acid Catalysis in Organic Reactions Part 1
Reaction Detail 1: Nucleophilic Substitution at Saturated Carbon
Basics 23: What Defines a Transition State?
Perspective 3: Bonding Beyond Hybridisation
Fundamental Knowledge Recap 1: Bond Lengths and Strengths
Fundamental Knowledge Recap 2: pKa
Section 3: A Focus on Shape
Habit 4: Representing Stereochemistry - Flying Wedge and Newman Projections
Basics 23: Isomerism in Organic Chemistry - Configurational Isomers
Habit 5: Getting Used to Drawing Stereoisomers
Practice 9: Getting Used to Stereoisomers
Habit 6: Assignment of Stereochemistry - The Cahn-Ingold-Prelog Rules
Practice 10: Assigning Stereochemistry
Habit 7: Stereoisomers with Symmetry
Basics 25: Properties of Stereoisomers
Reaction Detail 2: Stereochemical Aspects of Substitution Reactions
Common Error 6: Substitution Reactions
Reaction Detail 3: Substitution with Retention of Configuration
Common Error 7: Stereochemical Errors
Section 4: Types of Selectivity
Basics 26: Selectivity in Organic Chemistry - Chemoselectivity
Basics 27: Selectivity in Organic Chemistry - Regioselectivity
Basics 28: Selectivity in Organic Chemistry - Stereoselectivity
Basics 29: Stereochemical Definitions Relating to Reactions
Section 5: Bonds Can Rotate
Basics 30: Isomerism in Organic Chemistry - Conformational Isomers
Practice 11: Conformational Analysis
Applications 1: Conformational Isomers 2
Applications 2: SN2 Substitution Reactions Forming Three-Membered Rings
Basics 31: Introduction to Cyclohexanes
Practice 12: Drawing Cyclohexanes
Applications 3: Substitution Reactions of Cyclohexanes
Basics 32: Quantifying Conformers of Cyclohexanes
Basics 33: More Conformers of Cyclohexanes and Related Compounds
Practice 13: Drawing More Complex Cyclohexanes
Common Error 8: Cyclohexanes
Section 6: Eliminating the Learning
Reaction Detail 4: Elimination Reactions
Perspective 4: A Continuum of Mechanisms
Basics 34: More Substituted Alkenes Are More Stable
Basics 35: Enthalpy Changes for Reactions Involving Anionic Species
Applications 4: Stereochemistry of Elimination Reactions
Basics 36: Stereospecificity
Applications 5: Elimination Reactions of Cyclohexanes
Common Error 9: Elimination Reaction
Reaction Detail 5: Allylic Substitution
Section 7: Building Skills
Worked Problem 1: Curly Arrows and Reaction Profiles
Worked Problem 2: Competing SN1 Substitution and E1 Elimination
Worked Problem 3: Competing SN2 Substitution and E2 Elimination
Worked Problem 4: Acid Catalysis in Organic Reactions Part 2
Worked Problem 5: Epoxide Opening Reactions
Worked Problem 6: Is cis-Cyclohexane-1,2-diol Really Achiral?
Worked Problem 7: The Furst-Plattner Rule
Worked Problem 8: SN2' Stereochemistry and Conformations
Worked Problem 9: Complex Substitution Stereochemistry
Worked Problem 10: Cyclisation Reactions
Solution to Problem 1: Curly Arrows and Reaction Profiles
Solution to Problem 2: Competing SN1 Substitution and E1 Elimination
Solution to Problem 3: Competing SN2 Substitution and E2 Elimination
Solution to Problem 4: Acid Catalysis in Organic Reactions Part 2
Solution to Problem 5: Epoxide Opening Reactions
Solution to Problem 6: Is cis-Cyclohexane-1,2-diol Really Achiral?
Solution to Problem 7: The Furst-Plattner Rule
Solution to Problem 8: SN2' Stereochemistry and Conformations
Solution to Problem 9: Complex Substitution Stereochemistry
Solution to Problem 10: Cyclisation Reactions