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Structure and Mechanisms

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ISBN-10: 0306462435

ISBN-13: 9780306462436

Edition: 4th 2004 (Revised)

Authors: Francis A. Carey, Richard J. Sundberg

List price: $49.50
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Description:

Since its original appearance in 1977, Advanced Organic Chemistry has found wide use as a text providing broad coverage of the structure, reactivity and synthesis of organic compounds. The Fourth Edition provides updated material but continues the essential elements of the previous edition. The material in Part A is organized on the basis of fundamental structural topics such as structure, stereochemistry, conformation and aromaticity and basic mechanistic types, including nucleophilic substitution, addition reactions, carbonyl chemistry, aromatic substitution and free radical reactions. The material in Part B is organized on the basis of reaction type with emphasis on reactions of importance in laboratory synthesis. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews the fundamental concepts for each topic that is discussed. The Fourth Edition updates certain topics that have advanced rapidly in the decade since the Third Edition was published, including computational chemistry, structural manifestations of aromaticity, enantioselective reactions and lanthanide catalysis. The two parts stand alone, although there is considerable cross-referencing. Part A emphasizes quantitative and qualitative description of structural effects on reactivity and mechanism. Part B emphasizes the most general and useful synthetic reactions. The focus is on the core of organic chemistry, but the information provided forms the foundation for future study and research in medicinal and pharmaceutical chemistry, biological chemistry and physical properties of organic compounds.
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Book details

List price: $49.50
Edition: 4th
Copyright year: 2004
Publisher: Springer
Publication date: 9/30/2004
Binding: Paperback
Pages: 823
Size: 7.00" wide x 9.75" long x 2.00" tall
Weight: 3.894
Language: English

Francis A. Carey, a native of Pennsylvania, was educated in the public schools of Philadelphia, at Drexel University. Following postdoctoral work at Harvard and military service, he was appointed to the chemistry faculty of the University of Virginia in 1966.

Chemical Bonding and Structure
Valence Bond Description of Chemical Bonding
Orbital Hybridization
Resonance
Bond Energy, Polarity, and Polarizability
Bond Energies
Electronegativity and Polarity
Polarizability--Hardness and Softness
Molecular Orbital Theory and Methods
Huckel Molecular Orbital Theory
Qualitative Application of Molecular Orbital Theory
Application of Molecular Orbital Theory to Reactivity
Interactions between [sigma] and [pi] Systems--Hyperconjugation
Other Quantitative Descriptions of Molecular Structure
Atoms in Molecules
Electron Density Functionals
Modern Valence Bond Approaches
General References
Problems
Principles of Stereochemistry
Enantiomeric Relationships
Diastereomeric Relationships
Stereochemistry of Reactions
Prochiral Relationships
General References
Problems
Conformational, Steric, and Stereoelectronic Effects
Strain and Molecular Mechanics
Conformations of Acyclic Molecules
Conformations of Cyclohexane Derivatives
Carbocyclic Rings Other Than Six-Membered
The Effect of Heteroatoms on Conformational Equilibria
The Anomeric Effect
Conformational Effects on Reactivity
Angle Strain and Its Effect on Reactivity
Relationships between Ring Size and Rate of Cyclization
Torsional and Stereoelectronic Effects on Reactivity
General References
Problems
Study and Description of Organic Reaction Mechanismns
Thermodynamic Data
Kinetic Data
Substituent Effects and Linear Free-Energy Relationships
Basic Mechanistic Concepts: Kinetic versus Thermodynamic Control, Hammond's Postulate, the Curtin-Hammett Principle
Kinetic versus Thermodynamic Control
Hammond's Postulate
The Curtin-Hammett Principle
Isotope Effects
Isotopes in Labeling Experiments
Characterization of Reaction Intermediates
Catalysis by Bronsted Acids and Bases
Lewis Acid Catalysis
Solvent Effects
Substituent Effects in the Gas Phase
Stereochemistry
Conclusion
General References
Problems
Nucleophilic Substitution
The Limiting Cases--Substitution by the Ionization (S[subscript N]1) Mechanism
The Limiting Cases--Substitution by the Direct Displacement (S[subscript N]2) Mechanism
Detailed Mechanistic Description and Borderline Mechanisms
Carbocations
Nucleophilicity and Solvent Effects
Leaving-Group Effects
Steric and Strain Effects on Substitution and Ionization Rates
Effects of Conjugation on Reactivity
Stereochemistry of Nucleophilic Substitution
Neighboring-Group Participation
Mechanism of Rearrangements of Carbocations
The Norbornyl Cation and Other Nonclassical Carbocations
General References
Problems
Polar Addition and Elimination Reactions
Addition of Hydrogen Halides to Alkenes
Acid-Catalyzed Hydration and Related Addition Reactions
Addition of Halogens
Electrophilic Additions Involving Metal Ions
Additions to Alkynes and Allenes
The E2, E1, and E1cb Mechanisms
Regiochemistry of Elimination Reactions
Stereochemistry of E2 Elimination Reactions
Dehydration of Alcohols
Eliminations Not Involving C--H Bonds
General References
Problems
Carbanions and Other Nucleophilic Carbon Species
Acidity of Hydrocarbons
Carbanions Stabilized by Functional Groups
Enols and Enamines
Carbanions as Nucleophiles in S[subscript N]2 Reactions
General References
Problems
Reactions of Carbonyl Compounds
Hydration and Addition of Alcohols to Aldehydes and Ketones
Addition-Elimination Reactions of Ketones and Aldehydes
Addition of Carbon Nucleophiles to Carbonyl Groups
Reactivity of Carbonyl Compounds toward Addition
Ester Hydrolysis
Aminolysis of Esters
Amide Hydrolysis
Acylation of Nucleophilic Oxygen and nitrogen Groups
Intramolecular Catalysis
General References
Problems
Aromaticity
The Concept of Aromaticity
The Annulenes
Aromaticity in Charged Rings
Homoaromaticity
Fused-Ring Systems
Heterocyclic Rings
General References
Problems
Aromatic Substitution
Electrophilic Aromatic Substitution Reactions
Structure-Reactivity Relationships
Reactivity of Polycyclic and Heteroaromatic Compounds
Specific Substitution Mechanisms
Nitration
Halogenation
Protonation and Hydrogen Exchange
Friedel-Crafts Alkylation and Related Reactions
Friedel-Crafts Acylation and Related Reactions
Coupling with Diazonium Compounds
Substitution of Groups Other Than Hydrogen
Nucleophilic Aromatic Substitution by the Addition-Elimination Mechanism
Nucleophilic Aromatic Substitution by the Elimination-Addition Mechanism
General References
Problems
Concerted Pericyclic Reactions
Electrocyclic Reactions
Sigmatropic Rearrangements
Cycloaddition Reactions
General References
Problems
Free-Radical Reactions
Generation and Characterization of Free Radicals
Background
Stable and Persistent Free Radicals
Direct Detection of Radical Intermediates
Sources of Free Radicals
Structural and Stereochemical Properties of Radical Intermediates
Charged Radical Species
Characteristics of Reaction Mechanisms Involving Radical Intermediates
Kinetic Characteristics of Chain Reactions
Structure-Reactivity Relationships
Free-Radical Substitution Reactions
Halogenation
Oxidation
Free-Radical Addition Reactions
Addition of Hydrogen Halides
Addition of Halomethanes
Addition of Other Carbon Radicals
Addition of Thiols and Thiocarboxylic Acids
Halogen, Sulfur, and Selenium Group Transfer Reactions
Intramolecular Free-Radical Reactions
Rearrangement and Fragmentation Reactions of Free Radicals
Rearrangement Reactions
Fragmentation
Electron-Transfer Reactions Involving Transition-Metal Ions
S[subscript RN]1 Substitution Processes
General References
Problems
Photochemistry
General Principles
Orbital Symmetry Considerations Related to Photochemical Reactions
Photochemistry of Carbonyl Compounds
Photochemistry of Alkenes and Dienes
Photochemistry of Aromatic Compounds
General References
Problems
References to Problems
Index