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Contents

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 DS 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

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