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Summary: Publisher Summary 1 Part A of a new edition of a two-volume text on organic chemistry that aims to solidify and extend the student's understanding of basic concepts and to illustrate how structural changes influence mechanism and reactivity. In this volume, Francis A. Carey and Richard J. Sundberg (U. of Virginia) update the fundamental topics of structure and mechanism. Topics include molecular structure (chemical bonding, stereochemistry, and conformation); methods for characterization of reaction mechanisms; aromaticity; fundamental reaction types (nucleophilic substitution, addition and elimination, carbanions, carbonyl chemistry, aromatic substitution, pericyclic and free radical reactions, and photochemistry). Annotation c. Book News, Inc., Portland, OR (booknews.com) Publisher Summary 2 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. The New Revised 5th Edition will be available shortly. For details, click on the link in the right-hand column.

Table Of Contents:

Chemical Bonding and Structure 1(74)

Valence Bond Description of Chemical Bonding 2(11)

Orbital Hybridization 4(5)

Resonance 9(4)

Bond Energy, Polarity, and Polarizability 13(10)

Bond Energies 13(2)

Electronegativity and Polarity 15(5)

Polarizability---Hardness and Softness 20(3)

Molecular Orbital Theory and Methods 23(8)

Huckel Molecular Orbital Theory 31(5)

Qualitative Application of Molecular Orbital Theory 36(10)

Application of Molecular Orbital Theory to Reactivity 46(8)

Interactions between σ and π Systems---Hyperconjugation 54(3)

Other Quantitative Descriptions of Molecular Structure 57(18)

Atom in Molecules 57(2)

Electron Density Functionals 59(5)

Modern Valence Bond Approaches 64(1)

General References 65(1)

Problems 65(10)

Principles of Stereochemistry 75(48)

Enantiomeric Relationships 76(8)

Diastereomeric Relationships 84(13)

Stereochemistry of Reactions 97(8)

Prochiral Relationships 105(9)

General References 114(1)

Problems 114(9)

Conformational, Steric, and Stereoelectronic Effects 123(64)

Strain and Molecular Mechanics 124(5)

Conformations of Acyclic Molecules 129(6)

Conformations of Cyclohexane Derivatives 135(11)

Carbocyclic Rings Other Than Six-Membered 146(3)

The Effect of Heteroatoms on Conformational Equilibria 149(2)

The Anomeric Effect 151(6)

Conformational Effects on Reactivity 157(5)

Angle Strain and Its Effect on Reactivity 162(4)

Relationships between Ring Size and Rate of Cyclization 166(5)

Torsional and Stereoelectronic Effects on Reactivity 171(16)

General References 177(1)

Problems 177(10)

Study and Description of Organic Reaction Mechanismns 187(76)

Thermodynamic Data 187(5)

Kinetic Data 192(12)

Substituent Effects and Linear Free-Energy Relationships 204(11)

Basic Mechanistic Concepts: Kinetic versus thermodynamic Control, Hammond's Postulate, the Curtin--Hammett Principle 215(7)

Kinetic versus Thermodynamic Control 215(2)

Hammond's Postulate 217(3)

The Curtin--Hammett Principle 220(2)

Isotope Effects 222(3)

Isotopes in Labeling Experiments 225(1)

Characterization of Reaction Intermediates 226(2)

Catalysis by Bronsted Acids and Bases 228(5)

Lewis Acid Catalysis 233(4)

Solvent Effects 237(6)

Substituent Effects in the Gas Phase 243(4)

Stereochemistry 247(1)

Conclusion 248(15)

General References 248(2)

Problems 250(13)

Nucleophilic Substitution 263(88)

The Limiting Cases---Substitution by the Ionization (SN1) Mechanism 264(3)

The Limiting Cases---Substitution by the Direct Displacement (SN2) Mechanism 267(2)

Detailed Mechanistic Description and Borderline Mechanisms 269(7)

Carbocations 276(14)

Nucleophilicity and Solvent Effects 290(5)

Leaving-Group Effects 295(3)

Steric and Strain Effects on Substitution and Ionization Rates 298(2)

Effects of Conjugation on Reactivity 300(2)

Stereochemistry of Nucleophilic Substitution 302(7)

Neighboring-Group Participation 309(7)

Mechanism of Rearrangements of Carbocations 316(11)

The Norbornyl Cation and Other Nonclassical Carbocations 327(24)

General References 334(1)

Problems 335(16)

Polar Addition and Elimination Reactions 351(54)

Addition of Hydrogen Halides to Alkenes 352(6)

Acid-Catalyzed Hydration and Related Addition Reactions 358(3)

Addition of Halogens 361(8)

Electrophilic Additions Involving Metal Ions 369(2)

Additions to Alkynes and Allenes 371(7)

The E2, E1, and E1cb Mechanisms 378(5)

Regiochemistry of Elimination Reactions 383(3)

Stereochemistry of E2 Elimination Reactions 386(6)

Dehydration of Alcohols 392(1)

Eliminations Not Involving C--H Bonds 393(12)

General References 398(1)

Problems 398(7)

Carbanions and Other Nucleophilic Carbon Species 405(44)

Acidity of Hydrocarbons 405(11)

Carbanions Stabilized by Functional Groups 416(9)

Enols and Enamines 425(7)

Carbanions as Nucleophiles in SN2 Reactions 432(17)

General References 439(1)

Problems 440(9)

Reactions of Carbonyl Compounds 449(60)

Hydration and Addition of Alcohols to Aldehydes and Ketones 449(7)

Addition--Elimination Reactions of Ketones and Aldehydes 456(6)

Addition of Carbon Nucleophiles to Carbonyl Groups 462(8)

Reactivity of Carbonyl Compounds toward Addition 470(4)

Ester Hydrolysis 474(5)

Aminolysis of Esters 479(2)

Amide Hydrolysis 481(3)

Acylation of Nucleophilic Oxygen and Nitrogen Groups 484(4)

Intramolecular Catalysis 488(21)

General References 495(1)

Problems 496(13)

Aromaticity 509(42)

The Concept of Aromaticity 509(5)

The Annulenes 514(10)

Aromaticity in Charged Rings 524(5)

Homoaromaticity 529(1)

Fused-Ring Systems 530(10)

Heterocyclic Rings 540(11)

General References 543(1)

Problems 543(8)

Aromatic Substitution 551(54)

Electrophilic Aromatic Substitution Reactions 551(6)

Structure--Reactivity Relationships 557(11)

Reactivity of Polycyclic and Heteroaromatic Compounds 568(3)

Specific Substitution Mechanisms 571(18)

Nitration 571(4)

Halogenation 575(4)

Protonation and Hydrogen Exchange 579(1)

Friedel--Crafts Alkylation and Related Reactions 580(3)

Friedel--Crafts Acylation and Related Reactions 583(4)

Coupling with Diazonium Compounds 587(1)

Substitution of Groups Other Than Hydrogen 588(1)

Nucleophilic Aromatic Substitution by the Addition--Elimination Mechanism 589(4)

Nucleophilic Aromatic Substitution by the Elimination--Addition Mechanism 593(12)

General References 597(1)

Problems 597(8)

Concerted Pericyclic Reactions 605(58)

Electrocyclic Reactions 606(13)

Sigmatropic Rearrangements 619(17)

Cycloaddition Reactions 636(27)

General References 651(1)

Problems 651(12)

Free-Radical Reactions 663(80)

Generation and Characterization of Free Radicals 663(20)

Background 663(1)

Stable and Persistent Free Radicals 664(3)

Direct Detection of Radical Intermediates 667(5)

Sources of Free Radicals 672(3)

Structural and Stereochemical Properties of Radical Intermediates 675(5)

Charged Radical Species 680(3)

Characteristics of Reaction Mechanisms Involving Radical Intermediates 683(20)

Kinetic Characteristics of Chain Reactions 683(2)

Structure--Reactivity Relationships 685(18)

Free-Radical Substitution Reactions 703(5)

Halogenation 703(3)

Oxidation 706(2)

Free-Radical Addition Reactions 708(6)

Addition of Hydrogen Halides 708(4)

Addition of Halomethanes 712(1)

Addition of Other Carbon Radicals 713(1)

Addition of Thiols and Thiocarboxylic Acids 714(1)

Halogen, Sulfur, and Selenium Group Transfer Reactions 714(4)

Intramolecular Free-Radical Reactions 718(1)

Rearrangement and Fragmentation Reactions of Free Radicals 719(5)

Rearrangement Reactions 719(3)

Fragmentation 722(2)

Electron-Transfer Reactions Involving Transition-Metal Ions 724(3)

SRN1 Substitution Processes 727(16)

General References 733(1)

Problems 734(9)

Photochemistry 743(48)

General Principles 743(4)

Orbital Symmetry Considerations Related to Photochemical Reactions 747(6)

Photochemistry of Carbonyl Compounds 753(13)

Photochemistry of Alkenes and Dienes 766(13)

Photochemistry of Aromatic Compounds 779(12)

General References 781(1)

Problems 781(10)
References to Problems 791(16)
Index 807

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