Structure and mechanisms

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Structure and mechanisms / Francis A. Carey and Richard J. Sundberg

版:

5th ed

資料種別:

図書

出版情報:

New York, NY : Springer, c2007

形態:

xxi, 1199 p., [2] p. of plates ; 26 cm

シリーズ名:

Advanced organic chemistry / Francis A. Carey and Richard J. Sundberg ; pt. A <BA82789023>

著者名:

ISBN:

9780387448978 [0387448977] (: hard)
9780387683461 [0387683461] (: pbk)

書誌ID:

BA82789114

子書誌情報

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書誌詳細

注記:

Includes bibliographical references (p. 1155-1169) and index

主題:

Chemistry, Organic

言語:

英語

目次情報:

Structure and Mechanisms / Part A：

Chemical Bonding and Structure

Stereochemistry, Conformation and Stereoselectivity

Structural Effects on Stability and Reactivity

Nucleophilic Substitution

Polar Addition and Elimination Reactions

Carbanions and Other Carbon Nucleophiles

Addition, Condensation and Substitution Reactions of Carbonyl Compounds

Aromaticity

Aromatic Substitution

Concerted Pericyclic Reactions

Free Radical Reactions

Photochemistry

Preface

Acknowledgment and Personal Statement

Introduction

Chemical Bonding and Molecular Structure / Chapter 1：

Description of Molecular Structure Using Valence Bond Concepts / 1.1：

Hybridization / 1.1.1：

The Origin of Electron-Electron Repulsion / 1.1.2：

Electronegativity and Polarity / 1.1.3：

Electronegativity Equalization / 1.1.4：

Differential Electronegativity of Carbon Atoms / 1.1.5：

Polarizability, Hardness, and Softness / 1.1.6：

Resonance and Conjugation / 1.1.7：

Hyperconjugation / 1.1.8：

Covalent and van der Waals Radii of Atoms / 1.1.9：

Molecular Orbital Theory and Methods / 1.2：

The Huckel MO Method / 1.2.1：

Semiempirical MO Methods / 1.2.2：

Ab Initio Methods / 1.2.3：

Pictorial Representation of MOs for Molecules / 1.2.4：

Qualitative Application of MO Theory to Reactivity: Perturbational MO Theory and Frontier Orbitals / 1.2.5：

Numerical Application of MO Theory / 1.2.6：

Electron Density Functionals / 1.3：

Representation of Electron Density Distribution / 1.4：

Mulliken Population Analysis / 1.4.1：

Natural Bond Orbitals and Natural Population Analysis / 1.4.2：

Atoms in Molecules / 1.4.3：

Comparison and Interpretation of Atomic Charge Calculations / 1.4.4：

Electrostatic Potential Surfaces / 1.4.5：

Relationships between Electron Density and Bond Order / 1.4.6：

The Origin of the Rotational (Torsional) Barrier in Ethane and Other Small Molecules / Topic 1.1：

Heteroatom Hyperconjugation (Anomeric Effect) in Acyclic Molecules / Topic 1.2：

Bonding in Cyclopropane and Other Small Ring Compounds / Topic 1.3：

Representation of Electron Density by the Laplacian Function / Topic 1.4：

Application of Density Functional Theory to Chemical Properties and Reactivity / Topic 1.5：

DFT Formulation of Chemical Potential, Electronegativity, Hardness and Softness, and Covalent and van der Waal Radii / T.1.5.1：

DFT Formulation of Reactivity-The Fukui Function / T.1.5.2：

DFT Concepts of Substituent Groups Effects / T.1.5.3：

General References

Problems

Stereochemistry, Conformation, and Stereoselectivity / Chapter 2：

Configuration / 2.1：

Configuration at Double Bonds / 2.1.1：

Configuration of Cyclic Compounds / 2.1.2：

Configuration at Tetrahedral Atoms / 2.1.3：

Molecules with Multiple Stereogenic Centers / 2.1.4：

Other Types of Stereogenic Centers / 2.1.5：

The Relationship between Chirality and Symmetry / 2.1.6：

Configuration at Prochiral Centers / 2.1.7：

Resolution-The Separation of Enantiomers / 2.1.8：

Conformation / 2.2：

Conformation of Acyclic Compounds / 2.2.1：

Conformations of Cyclohexane Derivatives / 2.2.2：

Conformations of Carbocyclic Rings of Other Sizes / 2.2.3：

Molecular Mechanics / 2.3：

Stereoselective and Stereospecific Reactions / 2.4：

Examples of Stereoselective Reactions / 2.4.1：

Examples of Stereospecific Reactions / 2.4.2：

Enantioselective Reactions / 2.5：

Enantioselective Hydrogenation / 2.5.1：

Enantioselective Reduction of Ketones / 2.5.2：

Enantioselective Epoxidation of Allylic Alcohols / 2.5.3：

Enantioselective Dihydroxylation of Alkenes / 2.5.4：

Double Stereodifferentiation: Reinforcing and Competing Stereoselectivity / 2.6：

Analysis and Separation of Enantiomeric Mixtures / Topic 2.1：

Chiral Shift Reagents and Chiral Solvating Agents / T.2.1.1：

Separation of Enantiomers / T.2.1.2：

Enzymatic Resolution and Desymmetrization / Topic 2.2：

Lipases and Esterases / T.2.2.1：

Proteases and Acylases / T.2.2.2：

Epoxide Hydrolases / T.2.2.3：

The Anomeric Effect in Cyclic Compounds / Topic 2.3：

Polar Substituent Effects in Reduction of Carbonyl Compounds / Topic 2.4：

Thermodynamic Stability / Chapter 3：

Relationship between Structure and Thermodynamic Stability for Hydrocarbons / 3.1.1：

Calculation of Enthalpy of Formation and Enthalpy of Reaction / 3.1.2：

Chemical Kinetics / 3.2：

Fundamental Principles of Chemical Kinetics / 3.2.1：

Representation of Potential Energy Changes in Reactions / 3.2.2：

Reaction Rate Expressions / 3.2.3：

Examples of Rate Expressions / 3.2.4：

General Relationships between Thermodynamic Stability and Reaction Rates / 3.3：

Kinetic versus Thermodynamic Control of Product Composition / 3.3.1：

Correlations between Thermodynamic and Kinetic Aspects of Reactions / 3.3.2：

Curtin-Hammett Principle / 3.3.3：

Electronic Substituent Effects on Reaction Intermediates / 3.4：

Carbocations / 3.4.1：

Carbanions / 3.4.2：

Radical Intermediates / 3.4.3：

Carbonyl Addition Intermediates / 3.4.4：

Kinetic Isotope Effects / 3.5：

Linear Free-Energy Relationships for Substituent Effects / 3.6：

Numerical Expression of Linear Free-Energy Relationships / 3.6.1：

Application of Linear Free-Energy Relationships to Characterization of Reaction Mechanisms / 3.6.2：

Catalysis / 3.7：

Catalysis by Acids and Bases / 3.7.1：

Lewis Acid Catalysis / 3.7.2：

Solvent Effects / 3.8：

Bulk Solvent Effects / 3.8.1：

Examples of Specific Solvent Effects / 3.8.2：

Acidity of Hydrocarbons / Topic 3.1：

Mechanisms for Nucleophilic Substitution / Chapter 4：

Substitution by the Ionization (S[subscript N]1) Mechanism / 4.1.1：

Substitution by the Direct Displacement (S[subscript N]2) Mechanism / 4.1.2：

Detailed Mechanistic Description and Borderline Mechanisms / 4.1.3：

Relationship between Stereochemistry and Mechanism of Substitution / 4.1.4：

Substitution Reactions of Alkyldiazonium Ions / 4.1.5：

Structural and Solvation Effects on Reactivity / 4.2：

Characteristics of Nucleophilicity / 4.2.1：

Effect of Solvation on Nucleophilicity / 4.2.2：

Leaving-Group Effects / 4.2.3：

Steric and Strain Effects on Substitution and Ionization Rates / 4.2.4：

Effects of Conjugation on Reactivity / 4.2.5：

Neighboring-Group Participation / 4.3：

Structure and Reactions of Carbocation Intermediates / 4.4：

Structure and Stability of Carbocations / 4.4.1：

Direct Observation of Carbocations / 4.4.2：

Competing Reactions of Carbocations / 4.4.3：

Mechanisms of Rearrangement of Carbocations / 4.4.4：

Bridged (Nonclassical) Carbocations / 4.4.5：

The Role Carbocations and Carbonium Ions in Petroleum Processing / Topic 4.1：

Addition of Hydrogen Halides to Alkenes / Chapter 5：

Acid-Catalyzed Hydration and Related Addition Reactions / 5.2：

Addition of Halogens / 5.3：

Sulfenylation and Selenenylation / 5.4：

Sulfenylation / 5.4.1：

Selenenylation / 5.4.2：

Addition Reactions Involving Epoxides / 5.5：

Epoxides from Alkenes and Peroxidic Reagents / 5.5.1：

Subsequent Transformations of Epoxides / 5.5.2：

Electrophilic Additions Involving Metal Ions / 5.6：

Solvomercuration / 5.6.1：

Argentation-the Formation of Silver Complexes / 5.6.2：

Synthesis and Reactions of Alkylboranes / 5.7：

Hydroboration / 5.7.1：

Reactions of Organoboranes / 5.7.2：

Enantioselective Hydroboration / 5.7.3：

Comparison of Electrophilic Addition Reactions / 5.8：

Additions to Alkynes and Allenes / 5.9：

Hydrohalogenation and Hydration of Alkynes / 5.9.1：

Halogenation of Alkynes / 5.9.2：

Mercuration of Alkynes / 5.9.3：

Overview of Alkyne Additions / 5.9.4：

Additions to Allenes / 5.9.5：

Elimination Reactions / 5.10：

The E2, E1 and E1cb Mechanisms / 5.10.1：

Regiochemistry of Elimination Reactions / 5.10.2：

Stereochemistry of E2 Elimination Reactions / 5.10.3：

Dehydration of Alcohols / 5.10.4：

Eliminations Reactions Not Involving C-H Bonds / 5.10.5：

Carbanion Character of Organometallic Compounds / Chapter 6：

Carbanions Stabilized by Functional Groups / 6.3：

Enols and Enamines / 6.4：

Carbanions as Nucleophiles in S[subscript N]2 Reactions / 6.5：

Substitution Reactions of Organometallic Reagents / 6.5.1：

Substitution Reactions of Enolates / 6.5.2：

Reactivity of Carbonyl Compounds toward Addition / Chapter 7：

Hydration and Addition of Alcohols to Aldehydes and Ketones / 7.2：

Condensation Reactions of Aldehydes and Ketones with Nitrogen Nucleophiles / 7.3：

Substitution Reactions of Carboxylic Acid Derivatives / 7.4：

Ester Hydrolysis and Exchange / 7.4.1：

Aminolysis of Esters / 7.4.2：

Amide Hydrolysis / 7.4.3：

Acylation of Nucleophilic Oxygen and Nitrogen Groups / 7.4.4：

Intramolecular Catalysis of Carbonyl Substitution Reactions / 7.5：

Addition of Organometallic Reagents to Carbonyl Groups / 7.6：

Kinetics of Qrganometallic Addition Reactions / 7.6.1：

Stereoselectivity of Organometallic Addition Reactions / 7.6.2：

Addition of Enolates and Enols to Carbonyl Compounds: The Aldol Addition and Condensation Reactions / 7.7：

The General Mechanisms / 7.7.1：

Mixed Aldol Condensations with Aromatic Aldehydes / 7.7.2：

Control of Regiochemistry and Stereochemistry of Aldol Reactions of Ketones / 7.7.3：

Aldol Reactions of Other Carbonyl Compounds / 7.7.4：

Criteria of Aromaticity / Chapter 8：

The Energy Criterion for Aromaticity / 8.1.1：

Structural Criteria for Aromaticity / 8.1.2：

Electronic Criteria for Aromaticity / 8.1.3：

Relationship among the Energetic, Structural, and Electronic Criteria of Aromaticity / 8.1.4：

The Annulenes / 8.2：

Cyclobutadiene / 8.2.1：

Benzene / 8.2.2：

1,3,5,7-Cyclooctatetraene / 8.2.3：

[10]Annulenes-1,3,5,7,9-Cyclodecapentaene Isomers / 8.2.4：

[12], [14], and [16]Annulenes / 8.2.5：

[18]Annulene and Larger Annulenes / 8.2.6：

Other Related Structures / 8.2.7：

Aromaticity in Charged Rings / 8.3：

Homoaromaticity / 8.4：

Fused-Ring Systems / 8.5：

Heteroaromatic Systems / 8.6：

Electrophilic Aromatic Substitution Reactions / Chapter 9：

Structure-Reactivity Relationships for Substituted Benzenes / 9.2：

Substituent Effects on Reactivity / 9.2.1：

Mechanistic Interpretation of the Relationship between Reactivity and Selectivity / 9.2.2：

Reactivity of Polycyclic and Heteroaromatic Compounds / 9.3：

Specific Electrophilic Substitution Reactions / 9.4：

Nitration / 9.4.1：

Halogenation / 9.4.2：

Protonation and Hydrogen Exchange / 9.4.3：

Friedel-Crafts Alkylation and Related Reactions / 9.4.4：

Friedel-Crafts Acylation and Related Reactions / 9.4.5：

Aromatic Substitution by Diazonium Ions / 9.4.6：

Substitution of Groups Other than Hydrogen / 9.4.7：

Nucleophilic Aromatic Substitution / 9.5：

Nucleophilic Aromatic Substitution by the Addition-Elimination Mechanism / 9.5.1：

Nucleophilic Aromatic Substitution by the Elimination-Addition Mechanism / 9.5.2：

Cycloaddition Reactions / Chapter 10：

The Diels-Alder Reaction / 10.2：

Stereochemistry of the Diels-Alder Reaction / 10.2.1：

Substituent Effects on Reactivity, Regioselectivity and Stereochemistry / 10.2.2：

Catalysis of Diels-Alder Reactions by Lewis Acids / 10.2.3：

Computational Characterization of Diels-Alder Transition Structures / 10.2.4：

Scope and Synthetic Applications of the Diels-Alder Reaction / 10.2.5：

Enantioselective Diels-Alder Reactions / 10.2.6：

Intramolecular Diels-Alder Reactions / 10.2.7：

1,3-Dipolar Cycloaddition Reactions / 10.3：

Relative Reactivity, Regioselectivity, Stereoselectivity, and Transition Structures / 10.3.1：

Scope and Applications of 1,3-Dipolar Cycloadditions / 10.3.2：

Catalysis of 1,3-Dipolar Cycloaddition Reactions / 10.3.3：

[2 + 2] Cycloaddition Reactions / 10.4：

Electrocyclic Reactions / 10.5：

Overview of Electrocyclic Reactions / 10.5.1：

Orbital Symmetry Basis for the Stereospecificity of Electrocyclic Reactions / 10.5.2：

Examples of Electrocyclic Reactions / 10.5.3：

Electrocyclic Reactions of Charged Species / 10.5.4：

Electrocyclization of Heteroatomic Trienes / 10.5.5：

Sigmatropic Rearrangements / 10.6：

Overview of Sigmatropic Rearrangements / 10.6.1：

[1,3]-, [1,5]-, and [1,7]-Sigmatropic Shifts of Hydrogen and Alkyl Groups / 10.6.2：

Overview of [3,3]-Sigmatropic Rearrangements / 10.6.3：

[2,3]-Sigmatropic Rearrangements / 10.6.4：

Application of DFT Concepts to Reactivity and Regiochemistry of Cycloaddition Reactions / Topic 10.1：

Generation and Characterization of Free Radicals / Chapter 11：

Background / 11.1.1：

Long-Lived Free Radicals / 11.1.2：

Direct Detection of Radical Intermediates / 11.1.3：

Generation of Free Radicals / 11.1.4：

Structural and Stereochemical Properties of Free Radicals / 11.1.5：

Substituent Effects on Radical Stability / 11.1.6：

Charged Radicals / 11.1.7：

Characteristics of Reactions Involving Radical Intermediates / 11.2：

Kinetic Characteristics of Chain Reactions / 11.2.1：

Determination of Reaction Rates / 11.2.2：

Structure-Reactivity Relationships / 11.2.3：

Free Radical Substitution Reactions / 11.3：

Oxygenation / 11.3.1：

Free Radical Addition Reactions / 11.4：

Addition of Hydrogen Halides / 11.4.1：

Addition of Halomethanes / 11.4.2：

Addition of Other Carbon Radicals / 11.4.3：

Addition of Thiols and Thiocarboxylic Acids / 11.4.4：

Examples of Radical Addition Reactions / 11.4.5：

Other Types of Free Radical Reactions / 11.5：

Halogen, Sulfur, and Selenium Group Transfer Reactions / 11.5.1：

Intramolecular Hydrogen Atom Transfer Reactions / 11.5.2：

Rearrangement Reactions of Free Radicals / 11.5.3：

S[subscript RN]1 Substitution Processes / 11.6：

S[subscript RN]1 Substitution Reactions of Alkyl Nitro Compounds / 11.6.1：

S[subscript RN]1 Substitution Reactions of Aryl and Alkyl Halides / 11.6.2：

Relationships between Bond and Radical Stabilization Energies / Topic 11.1：

Structure-Reactivity Relationships in Hydrogen Abstraction Reactions / Topic 11.2：

General Principles / Chapter 12：

Photochemistry of Alkenes, Dienes, and Polyenes / 12.2：

Cis-trans Isomerization / 12.2.1：

Photoreactions of Other Alkenes / 12.2.2：

Photoisomerization of 1,3-Butadiene / 12.2.3：

Orbital Symmetry Considerations for Photochemical Reactions of Alkenes and Dienes / 12.2.4：

Photochemical Electrocyclic Reactions / 12.2.5：

Photochemical Cycloaddition Reactions / 12.2.6：

Photochemical Rearrangements Reactions of 1,4-Dienes / 12.2.7：

Photochemistry of Carbonyl Compounds / 12.3：

Hydrogen Abstraction and Fragmentation Reactions / 12.3.1：

Cycloaddition and Rearrangement Reactions of Cyclic Unsaturated Ketones / 12.3.2：

Cycloaddition of Carbonyl Compounds and Alkenes / 12.3.3：

Photochemistry of Aromatic Compounds / 12.4：

Computational Interpretation of Diene and Polyene Photochemistry / Topic 12.1：

References to Problems

Index

Structure and Mechanisms / Part A：

Chemical Bonding and Structure

Stereochemistry, Conformation and Stereoselectivity

Structural Effects on Stability and Reactivity

Nucleophilic Substitution

Polar Addition and Elimination Reactions

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