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| Preface | |
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| Bonding | |
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| Atomic structure | |
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| The chemical bond | |
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| The periodic table | |
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| Valence electrons | |
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| Lewis structures | |
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| Conventions for drawing structures | |
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| Atomic orbital theory | |
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| Molecular orbital theory | |
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| Covalent bonding | |
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| Bonding in hydrocarbons | |
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| Bonding in compounds containing heteroatoms | |
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| Bonding in common functional groups | |
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| Electronic effects | |
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| Steric effects | |
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| Stereoelectronic effects | |
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| Double bond equivalents | |
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| Structure | |
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| Configuration | |
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| Geometrical isomerism | |
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| Optical isomerism | |
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| Representations of stereoisomers | |
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| Molecules with one stereogenic centre | |
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| Molecules with more than one stereogenic centre | |
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| Molecules with more than one stereogenic centre which are not optically active | |
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| Optically active molecules without stereogenic centres: molecular asymmetry | |
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| Asymmetric heteroatoms | |
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| Conformation | |
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| Representation of conformers | |
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| Open-chain compounds | |
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| Ring compounds | |
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| Summary of stereochemical relationships | |
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| Naturally occurring chiral compounds | |
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| Asymmetric synthesis | |
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| Enantioselective synthesis | |
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| Diastereoselective synthesis | |
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| Methods for the determination of enantiomeric purity | |
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| Reactivity | |
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| Thermodynamics | |
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| Gibbs free energy | |
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| Enthalpy | |
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| Entropy | |
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| Chemical equilibrium | |
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| Kinetics | |
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| Rates of reaction | |
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| Reactions with competing steps | |
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| Overcoming activation energy barriers | |
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| Reaction mechanism | |
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| What is reactivity? | |
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| Lewis acids and bases: 'philicity' | |
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| Polarisability effects: Hard-Soft Acid-Base theory | |
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| Curly ('curved') arrows | |
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| Classes of reaction mechanism | |
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| Polar mechanisms | |
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| Radical mechanisms | |
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| Pericyclic mechanisms | |
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| Ligand coupling reaction mechanisms | |
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| Principle of microscopic reversibility | |
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| Selectivity of reactions | |
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| Solvents in organic chemistry | |
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| Redox reactions in organic chemistry | |
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| Intermediates | |
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| Carbocations | |
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| Structure | |
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| Factors stabilising carbocations | |
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| Generation of carbocations | |
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| Rearrangements of carbocations | |
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| Carbanions | |
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| Structure | |
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| Carbanions derived from simple alkanes | |
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| Factors stabilising carbanions | |
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| Carbanions with covalent character | |
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| Grignard reagents (RMgX) | |
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| Organolithium reagents (RLi) | |
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| Organocadmium reagents | |
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| Radicals | |
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| Structure | |
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| Factors stabilising radicals | |
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| Generation of radicals | |
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| Carbenes | |
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| Stability and structure | |
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| Generation of carbenes | |
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| Benzynes | |
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| Stability and structure | |
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| Generation of benzynes | |
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| Ketenes | |
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| Stability and structure | |
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| Generation of ketenes | |
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| Acidity and Basicity | |
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| Lowry-Bronsted Acid-Base theory | |
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| Organic acidity | |
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| Organic acids | |
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| Organic basicity | |
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| Organic bases | |
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| Nucleophilic Substitution | |
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| The S[subscript N]1 reaction | |
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| Factors affecting the S[subscript N]1 reaction | |
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| The S[subscript N]2 reaction | |
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| Factors enhancing the S[subscript N]2 reaction | |
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| Synthetic applications of nucleophilic substitution reactions | |
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| Protecting-group chemistry | |
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| Stereocontrolled alkylation reactions | |
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| Addition Reactions | |
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| Electrophilic addition reactions | |
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| Addition of halogens | |
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| Addition of hydrogen halides | |
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| Addition of hydrogen halides to conjugated dienes | |
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| Addition of diborane (hydroboration) | |
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| Addition of hydrogen | |
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| Addition of oxygen | |
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| Addition of carbon | |
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| Nucleophilic addition reactions | |
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| Irreversible nucleophilic addition | |
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| Irreversible nucleophilic conjugate addition | |
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| Reversible nucleophilic addition | |
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| Additions to electron-deficient alkenes | |
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| Additions of ketenes | |
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| Synthetic applications | |
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| Elimination Reactions | |
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| Eliminations | |
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| E[subscript 1] reactions | |
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| E[subscript 1]CB reactions | |
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| E[subscript 2] reactions | |
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| Eliminations leading to isomeric products | |
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| Competition between substitution and elimination | |
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| The leaving group | |
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| Oxidation processes | |
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| [alpha]-Eliminations leading to carbenes and nitrenes | |
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| Eliminations of phosphorus | |
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| Eliminations of sulfur and selenium | |
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| Eliminations in protecting-group chemistry | |
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| Aromatic Substitution | |
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| Aromaticity | |
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| Benzene | |
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| Heteroaromatics | |
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| Reactions | |
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| Acidity and basicity | |
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| Electrophilic aromatic substitution | |
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| Orientation effects in electrophilic aromatic substitution (S[subscript E]Ar) | |
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| o-Lithiation | |
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| Nucleophilic aromatic substitution | |
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| Arene chromium tricarbonyl complexes | |
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| Sequential Addition and Elimination Reactions | |
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| Addition-elimination reactions | |
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| Addition of hydride | |
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| Addition of heteroatom nucleophiles | |
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| Addition of carbon nucleophiles | |
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| Addition of phosphorus nucleophiles | |
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| Addition-elimination reactions in conjugated systems | |
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| Addition-elimination reactions in heterocyclic systems | |
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| Addition-elimination reactions in ring-closing metathesis | |
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| Addition-elimination reactions in deprotections | |
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| Radical Reactions | |
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| Generation | |
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| Reactions | |
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| Termination | |
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| Propagation | |
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| Substitution | |
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| Addition reactions | |
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| Fragmentation | |
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| Rearrangement | |
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| Synthetic utility | |
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| Ligand Coupling Reactions | |
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| Palladium-mediated couplings | |
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| Palladium-mediated coupling processes | |
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| Heck coupling | |
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| Allylic coupling processes | |
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| Ligand coupling processes mediated by other elements | |
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| Copper | |
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| Magnesium | |
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| Lead | |
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| Pericyclic Reactions | |
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| Molecular orbitals and the FMO approach | |
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| Pericyclic reactions | |
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| Electrocyclic reactions | |
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| Cycloaddition reactions | |
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| Sigmatropic reactions | |
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| Synthetic applications of pericyclic reactions | |
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| Index | |