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Structure and Reactivity in Organic Chemistry

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ISBN-10: 1405114517

ISBN-13: 9781405114516

Edition: 2008

Authors: Mark G. Moloney

List price: $68.75
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Book details

List price: $68.75
Copyright year: 2008
Publisher: John Wiley & Sons, Incorporated
Publication date: 4/28/2008
Binding: Paperback
Pages: 318
Size: 6.50" wide x 9.50" long x 0.75" tall
Weight: 1.540
Language: English

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