Mark C. Elliott
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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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.
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