How to succeed in organic chemistry

An honest, motivating, and supportive guide to the essential principles of organic reaction mechanisms, which ingrains in the reader all the skills needed to be successful in their studies.

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