How to Succeed in Organic Chemistry

Dr Mark Elliott is Senior Lecturer in Organic Chemistry and Deputy Director of Learning and Teaching in the Department of Chemistry at Cardiff University. His research interests lie in the development of new synthetic methodology, and its application to target synthesis. He teaches organic chemistry at all levels of the undergraduate curriculum.

• Section 1: Laying the FoundationsBasics 1: Structures of Organic CompoundsHabit 1: Always Draw Structures with Realistic GeometryBasics 2: Functional Groups and "R" GroupsBasics 3: Naming Organic CompoundsPractice 1: Drawing Structures from Chemical NamesBasics 4: Isomerism in Organic Chemistry - Constitutional IsomersPractice 2: Constitutional Isomers and Chemical NamesHabit 2: Identifying When a Formula is PossiblePractice 3: Double Bond EquivalentsCommon Error 1: Formulae, Functional Groups and Double Bond EquivalentsHabit 3: Ignore What Doesn't ChangeBasics 5: Electronegativity, Bond Polarisation and Inductive EffectsPractice 4: Bond Polarisation and ElectronegativityBasics 6: Bonding in Organic CompoundsPractice 5: HybridisationBasics 7: Bonding and Antibonding OrbitalsBasics 8: Introduction to Curly ArrowsFundamental Reaction Type 1: Nucleophilic Substitution at Saturated CarbonPractice 6: Electronegativity in ContextFundamental Reaction Type 2: Elimination ReactionsSection 2: Building on the FoundationsBasics 9: Breaking Bonds DS Linking Curly Arrows and Molecular OrbitalsCommon Error 2: Curly ArrowsBasics 10: Conjugation and ResonanceBasics 11: Thermodynamic DefinitionsBasics 12: Bond Dissociation EnergyBasics 13: Calculating Enthalpy of Reaction from Bond Dissociation EnergiesPerspective 1: A Closer Look at Bond Dissociation EnergiesPractice 7: Calculating Enthalpy of Reaction from Bond Dissociation EnergyBasics 14: Energetics and Reaction ProfilesBasics 15: How Fast Are Reactions?Basics 16: Introduction to Carbocations, Carbanions and Free-RadicalsBasics 17: Carbocations 2 - More Factors Affecting StabilityBasics 18: Carbanions 2 - Stability and pKaPerspective 2: A Scale for Carbocation StabilityCommon Error 3: Methyl Groups are Electron-ReleasingPractice 8: Drawing Resonance Forms for Carbocations and CarbanionsCommon Error 4: ResonanceBasics 19: The Hammond PostulateBasics 20: Conjugation and Stability - The EvidenceCommon Error 5: Carbocations and CarbanionsBasics 21: Reactivity of Conjugated SystemsBasics 22: Acid Catalysis in Organic Reactions Part 1Reaction Detail 1: Nucleophilic Substitution at Saturated CarbonBasics 23: What Defines a Transition State?Perspective 3: Bonding Beyond HybridisationFundamental Knowledge Recap 1: Bond Lengths and StrengthsFundamental Knowledge Recap 2: pKaSection 3: A Focus on ShapeHabit 4: Representing Stereochemistry - Flying Wedge and Newman ProjectionsBasics 23: Isomerism in Organic Chemistry - Configurational IsomersHabit 5: Getting Used to Drawing StereoisomersPractice 9: Getting Used to StereoisomersHabit 6: Assignment of Stereochemistry - The Cahn-Ingold-Prelog RulesPractice 10: Assigning StereochemistryHabit 7: Stereoisomers with SymmetryBasics 25: Properties of StereoisomersReaction Detail 2: Stereochemical Aspects of Substitution ReactionsCommon Error 6: Substitution ReactionsReaction Detail 3: Substitution with Retention of ConfigurationCommon Error 7: Stereochemical ErrorsSection 4: Types of SelectivityBasics 26: Selectivity in Organic Chemistry - ChemoselectivityBasics 27: Selectivity in Organic Chemistry - RegioselectivityBasics 28: Selectivity in Organic Chemistry - StereoselectivityBasics 29: Stereochemical Definitions Relating to ReactionsSection 5: Bonds Can RotateBasics 30: Isomerism in Organic Chemistry - Conformational IsomersPractice 11: Conformational AnalysisApplications 1: Conformational Isomers 2Applications 2: SN2 Substitution Reactions Forming Three-Membered RingsBasics 31: Introduction to CyclohexanesPractice 12: Drawing CyclohexanesApplications 3: Substitution Reactions of CyclohexanesBasics 32: Quantifying Conformers of CyclohexanesBasics 33: More Conformers of Cyclohexanes and Related CompoundsPractice 13: Drawing More Complex CyclohexanesCommon Error 8: CyclohexanesSection 6: Eliminating the LearningReaction Detail 4: Elimination ReactionsPerspective 4: A Continuum of MechanismsBasics 34: More Substituted Alkenes Are More StableBasics 35: Enthalpy Changes for Reactions Involving Anionic SpeciesApplications 4: Stereochemistry of Elimination ReactionsBasics 36: StereospecificityApplications 5: Elimination Reactions of CyclohexanesCommon Error 9: Elimination ReactionReaction Detail 5: Allylic SubstitutionSection 7: Building SkillsWorked Problem 1: Curly Arrows and Reaction ProfilesWorked Problem 2: Competing SN1 Substitution and E1 EliminationWorked Problem 3: Competing SN2 Substitution and E2 EliminationWorked Problem 4: Acid Catalysis in Organic Reactions Part 2Worked Problem 5: Epoxide Opening ReactionsWorked Problem 6: Is cis-Cyclohexane-1,2-diol Really Achiral?Worked Problem 7: The Furst-Plattner RuleWorked Problem 8: SN2' Stereochemistry and ConformationsWorked Problem 9: Complex Substitution StereochemistryWorked Problem 10: Cyclisation ReactionsSolution to Problem 1: Curly Arrows and Reaction ProfilesSolution to Problem 2: Competing SN1 Substitution and E1 EliminationSolution to Problem 3: Competing SN2 Substitution and E2 EliminationSolution to Problem 4: Acid Catalysis in Organic Reactions Part 2Solution to Problem 5: Epoxide Opening ReactionsSolution to Problem 6: Is cis-Cyclohexane-1,2-diol Really Achiral?Solution to Problem 7: The Furst-Plattner RuleSolution to Problem 8: SN2' Stereochemistry and ConformationsSolution to Problem 9: Complex Substitution StereochemistrySolution to Problem 10: Cyclisation Reactions

I liked the slightly informal tone of writing, almost as if I was being taught one-to-one by the author. It felt personal and honest, as if the author wrote the book to help me personally.