Advanced Organic Chemistry. Structure and Mechanisms

Автор(ы):Carey Francis A., Sundberg Richard J.
06.10.2007
Описание: Книга первая посвящена рассмотрению природы химических связей и строения молекул, стереохимии, механизмам различных органических реакций и методам их изучения. Приведены многочисленные схемы конкретных реакций с указанием выходов продуктов и ссылками на оригинальную литературу. В конце каждой главы даны задачи, помогающие контролировать степень усвоения материала.
Оглавление:
Advanced Organic Chemistry. Structure and Mechanisms — обложка книги.
Chapter 1. Chemical Bonding and Structure [1]
  1.1. Valence Bond Description of Chemical Bonding [2]
    1.1.1. Orbital Hybridization [4]
    1.1.2 Resonance [9]
  1.2. Bond Energy, Polarity, and Polarizability [13]
    1.2.1. Bond Energies [13]
    1.2.2. Electronegativity and Polarity [15]
    1.2.3. Polarizability—Hardness and Softness [20]
  1.3. Molecular Orbital Theory and Methods [23]
  1.4. Huckel Molecular Orbital Theory [31]
  1.5. Qualitative Application of Molecular Orbital Theory [36]
  1.6. Application of Molecular Orbital Theory to Reactivity [46]
  1.7. Interactions between a and я Systems—Hyperconjugation [54]
  1.8. Other Quantitative Descriptions of Molecular Structure [57]
    1.8.1. Atoms in Molecules [57]
    1.8.2. Electron Density Functionals [59]
    1.8.3. Modern Valence Bond Approaches [64]
  General References [65]
  Problems [65]
Chapter 2. Principles of Stereochemistry [75]
  2.1. Enantiomeric Relationships [76]
  2.2. Diastereomeric Relationships [84]
  2.3. Stereochemistry of Reactions [97]
  2.4. Prochiral Relationships [105]
  General References [114]
  Problems [114]
Chapter 3. Conformational, Steric, and Stereoelectronic Effects [123]
  3.1. Strain and Molecular Mechanics [124]
  3.2. Conformations of Acyclic Molecules [129]
  3.3. Conformations of Cyclohexane Derivatives [135]
  3.4. Carbocyclic Rings Other Than Six-Membered [146]
  3.5. The Effect of Heteroatoms on Conformational Equilibria [149]
  3.6. The Anomeric Effect [151]
  3.7. Conformational Effects on Reactivity [157]
  3.8. Angle Strain and Its Effect on Reactivity [162]
  3.9. Relationships between Ring Size and Rate of Cyclization [166]
  3.10. Torsional and Stereoelectronic Effects on Reactivity [171]
  General References [177]
  Problems [177]
Chapter 4. Study and Description of Organic Reaction Mechanismns [187]
  4.1. Thermodynamic Data [187]
  4.2. Kinetic Data [192]
  4.3. Substituent Effects and Linear Free-Energy Relationships [204]
  4.4. Basic Mechanistic Concepts: Kinetic versus Thermodynamic Control, Hammond's Postulate, the Curtin-Hammett Principle [215]
    4.4.1. Kinetic versus Thermodynamic Control [215]
    4.4.2. Hammond's Postulate [217]
    4.4.3. The Curtin-Hammett Principle [220]
  4.5. Isotope Effects [222]
  4.6. Isotopes in Labeling Experiments [225]
  4.7. Characterization of Reaction Intermediates [226]
  4.8. Catalysis by Brensted Acids and Bases [228]
  4.9. Lewis Acid Catalysis [233]
  4.10. Solvent Effects [237]
  4.11. Substituent Effects in the Gas Phase [243]
  4.12. Stereochemistry [247]
  4.13. Conclusion [248]
  General References [248]
  Problems [250]
Chapter 5. Nucleophilic Substitution [263]
  5.1. The Limiting Cases—Substitution by the lonization (SN1) Mechanism [264]
  5.2. The Limiting Cases—Substitution by the Direct Displacement (SN2) Mechanism [267]
  5.3. Detailed Mechanistic Description and Borderline Mechanisms [269]
  5.4. Carbocations [276]
  5.5. Nucleophilicity and Solvent Effects [290]
  5.6. Leaving-Group Effects [295]
  5.7. Steric and Strain Effects on Substitution and lonization Rates [298]
  5.8. Effects of Conjugation on Reactivity [300]
  5.9. Stereochemistry of Nucleophilic Substitution [302]
  5.10. Neighboring-Group Participation [309]
  5.11. Mechanism of Rearrangements of Carbocations [316]
  5.12. The Norbornyl Cation and Other Nonclassical Carbocations [327]
  General References [334]
  Problems [335]
Chapter 6. Polar Addition and Elimination Reactions [351]
  6.1. Addition of Hydrogen Halides to Alkenes [352]
  6.2. Acid-Catalyzed Hydration and Related Addition Reactions [358]
  6.3. Addition of Halogens [361]
  6.4. Electrophilic Additions Involving Metal Ions [369]
  6.5. Additions to Alkynes and Allenes [371]
  6.6. The E2, El, and Elcb Mechanisms [378]
  6.7. Regiochemistry of Elimination Reactions [383]
  6.8. Stereochemistry of E2 Elimination Reactions [386]
  6.9. Dehydration of Alcohols [392]
  6.10. Eliminations Not Involving С—Н Bonds [393]
  General References [398]
  Problems [398]
Chapter 7. Carbanions and Other Nucleophilic Carbon Species [405]
  7.1. Acidity of Hydrocarbons [405]
  7.2. Carbanions Stabilized by Functional Groups [416]
  7.3. Enols and Enamines [425]
  7.4. Carbanions as Nucleophiles in SN2 Reactions [432]
  General References [439]
  Problems [440]
Chapter 8. Reactions of Carbonyl Compounds [449]
  8.1. Hydration and Addition of Alcohols to Aldehydes and Ketones [449]
  8.2. Addition—Elimination Reactions of Ketones and Aldehydes [456]
  8.3. Addition of Carbon Nucleophiles to Carbonyl Groups [462]
  8.4. Reactivity of Carbonyl Compounds toward Addition [470]
  8.5. Ester Hydrolysis [474]
  8.6. Aminolysis of Esters [479]
  8.7. Amide Hydrolysis [481]
  8.8. Acylation of Nucleophilic Oxygen and Nitrogen Groups [484]
  8.9. Intramolecular Catalysis [488]
  General References [495]
  Problems [496]
Chapter 9. Aromaticity [509]
  9.1. The Concept of Aromaticity [509]
  9.2. The Annulenes [514]
  9.3. Aromaticity in Charged Rings [524]
  9.4. Homoaromaticity [529]
  9.5. Fused-Ring Systems [530]
  9.6. Heterocyclic Rings [540]
  General References [543]
  Problems [543]
Chapter 10. Aromatic Substitution [551]
  10.1. Electrophilic Aromatic Substitution Reactions [551]
  10.2. Structure-Reactivity Relationships [557]
  10.3. Reactivity of Polycyclic and Heteroaromatic Compounds [568]
  10.4. Specific Substitution Mechanisms [571]
    10.4.1. Nitration [571]
    10.4.2. Halogenation [575]
    10.4.3. Protonation and Hydrogen Exchange [579]
    10.4.4. Friedel-Crafts Alkylation and Related Reactions [580]
    10.4.5. Friedel-Crafts Acylation and Related Reactions [583]
    10.4.6. Coupling with Diazonium Compounds [587]
    10.4.7. Substitution of Groups Other Than Hydrogen [588]
  10.5. Nucleophilic Aromatic Substitution by the Addition-Elimination Mechanism [589]
  10.6. Nucleophilic Aromatic Substitution by the Elimination-Addition Mechanism [593]
  General References [597]
  Problems [597]
Chapter 11. Concerted Pericyclic Reactions [605]
  11.1. Electrocyclic Reactions [606]
  11.2. Sigmatropic Rearrangements [619]
  11.3. Cycloaddition Reactions [636]
  General References [651]
  Problems [651]
Chapter 12. Free-Radical Reactions [663]
  12.1. Generation and Characterization of Free Radicals [663]
    12.1.1. Background [663]
    12.1.2. Stable and Persistent Free Radicals [664]
    12.1.3. Direct Detection of Radical Intermediates [667]
    12.1.4. Sources of Free Radicals [672]
    12.1.5. Structural and Stereochemical Properties of Radical Intermediates [675]
    12.1.6. Charged Radical Species [680]
  12.2. Characteristics of Reaction Mechanisms Involving Radical Intermediates [683]
    12.2.1. Kinetic Characteristics of Chain Reactions [683]
    12.2.2. Structure-Reactivity Relationships [685]
  12.3. Free-Radical Substitution Reactions [703]
    12.3.1. Halogenation [703]
    12.3.2. Oxidation [706]
  12.4. Free-Radical Addition Reactions [708]
    12.4.1. Addition of Hydrogen Halides [708]
    12.4.2. Addition of Halomethanes [712]
    12.4.3. Addition of Other Carbon Radicals [713]
    12.4.4. Addition of Thiols and Thiocarboxylic Acids [714]
  12.5. Halogen, Sulfur, and Selenium Group Transfer Reactions [714]
  12.6. Intramolecular Free-Radical Reactions [718]
  12.7. Rearrangement and Fragmentation Reactions of Free Radicals [719]
    12.7.1. Rearrangement Reactions [719]
    12.7.2. Fragmentation [722]
  12.8. Electron-Transfer Reactions Involving Transition-Metal Ions [724]
  12.9. SRN1 Substitution Processes [727]
  General References [733]
  Problems [734]
Chapter 13. Photochemistry [743]
  13.1. General Principles [743]
  13.2. Orbital Symmetry Considerations Related to Photochemical Reactions [747]
  13.3. Photochemistry of Carbonyl Compounds [753]
  13.4. Photochemistry of Alkenes and Dienes [766]
  13.5. Photochemistry of Aromatic Compounds [779]
  General References [781]
  Problems [781]
References to Problems [791]
Index [807]
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