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WorldCat.org

1 BONDING AND ELECTRON DISTRIBUTION 1     1.1 The Decision-Based Approach To Organic Chemistry 2       1.2 Ionic And Covalent Bonding 6     1.3 Lewis Structures And Resonance Forms 8     1.4 Curved-Arrow Notation 11     1.5 Nomenclature And Abbreviations 16     1.6 An Orbital View Of Bonding (Supplemental) 18     1.7 The Shapes Of Molecules 21     1.8 Molecular Repulsions, Attractions, And Hydrogen Bonding 25     1.9 Conjugation, Vinylogy, Aromaticity 27     1.10  Summary 30     2  THE PROCESS OF BOND FORMATION 34     2.1 Energetics Control Knowledge 35     2.2 Orbital Overlap In Covalent Bond Formation 35     2.3 Orbital Interaction Diagrams 38     2.4 Polarizability And Hard And Soft Acid-Base Theory 41     2.5 Thermodynamics, Position Of Equilibrium 43     2.6 Kinetics, Rate Of Reaction 47     2.7 Solvent Stabilization Of Ions 53     2.8 Enzymatic Catalysis - Lessons From Biochemistry 55     2.9 Summary 57     3  PROTON TRANSFER AND THE PRINCIPLES OF STABILITY 61     3.1 Introduction To Proton Transfer 62     3.2 Ranking Of Acids And Bases, The pKa Chart 63     3.3 Structural Factors That Influence Acid Strength 66     3.4 Structural Factors That Influence Base Strength 70     3.5 Carbon Acids & Ranking Of Electron-Withdrawing Groups 71     3.6 Calculation Of Keq For Proton Transfer 76     3.7 Proton Transfer Mechanisms 77     3.8 Common Errors 81     3.9 Proton Transfer Product Predictions 82     3.10  Summary 83     4  IMPORTANT REACTION ARCHETYPES  88     4.1 Introduction To Reaction Archetypes 89     4.2 Nucleophilic Substitution At A Tetrahedral Center 89     4.3 Elimination Reactions Create Pi Bonds 110     4.4 Addition Reactions To Polarized Multiple Bonds 124     4.5 Nucleophilic Substitution At A Trigonal Planar Center 133      4.6 Electrophilic Substitution At A Trigonal Planar Center 140     4.7 Rearrangements To An Electrophilic Carbon 144     4.8 Reaction Archetype Summary 146     5  CLASSIFICATION OF ELECTRON SOURCES 151      5.1 Generalized Ranking Of Electron Sources 151     5.2 Nonbonding Electrons 152     5.3 Electron-Rich Sigma Bonds 154     5.4 Electron-Rich Pi Bonds 155     5.5 Simple Pi Bonds 156     5.6 Aromatic Rings 159     5.7 Summary Of Generic Electron Sources 160     6  CLASSIFICATION OF ELECTRON SINKS 166     6.1 Generalized Ranking Of Electron Sinks 166     6.2 Electron-Deficient Species 167     6.3 Weak Single Bonds 168     6.4 Polarized Multiple Bonds Without Leaving Groups 170     6.5 Polarized Multiple Bonds With Leaving Groups 172     6.6 Summary Of Generic Electron Sinks 173     7  THE ELECTRON FLOW PATHWAYS 179      7.1 The Dozen Most Common Pathways 180     7.2 Six Minor Pathways 191     7.3 Common Path Combinations 197     7.4 Variations On A Theme 201     7.5 Twelve Major Paths Summary And Crosschecks 208     8  INTERACTION OF ELECTRON SOURCES AND SINKS 213     8.1 Source And Sink Correlation Matrix 214     8.2 H-A Sinks Reacting With Common Sources 214     8.3 Y-L Sinks Reacting With Common Sources 218     8.4 sp3 C-L Sinks Reacting With Common Sources 222     8.5 C=Y Sinks Reacting With Common Sources 227     8.6 R-C   Y Sinks Reacting With Common Sources 233     8.7 C=C?Ewg Sinks Reacting With Common Sources 235     8.8 L-C=Y Sinks Reacting With Common Sources 237     8.9 Miscellaneous Reactions 240     8.10  Metal Ions As Electron Sinks 242     8.11  Rearrangements To An Electrophilic Center 243     8.12  Nu-L Reactions 244     8.13  Product Matrix Summary 248     9  DECISIONS, DECISIONS 251      9.1 Decision Point Recognition 252     9.2 Multiple Additions 252     9.3 Regiochemistry & Stereochemistry Of Enolate Formation 254     9.4 Ambident Nucleophiles 255     9.5 Substitution Vs. Elimination 258     9.6 Ambident Electrophiles 262     9.7 Intermolecular Vs. Intramolecular 263     9.8 To Migrate Or Not To An Electrophilic Center 264     9.8 Summary 266     10 CHOOSING THE MOST PROBABLE PATH  269      10.1  Problem-Solving In General 270     10.2  General Mechanistic Cross-Checks 274     10.3  The Path-Selection Process 276     10.4  Reaction Mechanism Strategies 278     10.5  Worked Mechanism Examples 279     10.6  Product Prediction Strategies 297     10.7  Worked Product Prediction Examples 297     10.8  Methods For Testing Mechanisms 313     10.9  Lessons from Biochemical Mechanisms 319     10.10 Summary 321     11 ONE-ELECTRON PROCESSES 326      11.1  Radical Structure And Stability 326     11.2  Radical Path Initiation 329     11.3  Major Paths For Radicals Reacting With Neutrals 330     11.4  Unimolecular Radical Paths 332     11.5  Termination Radical Paths 333     11.6  Radical Path Combinations 333     11.7  Approaches To Radical Mechanisms 336     11.8  Single Electron Transfer, S.E.T., And Charged Radicals 338     11.9  Dissolving Metal Reductions 339     11.10 Electron Transfer Initiated Processes 340     11.11 One-Electron Path Summary 340     12 QUALITATIVE M.O. THEORY & PERICYCLIC REACTIONS  343      12.1  Review Of Orbitals As Standing Waves 344     12.2  Molecular Orbital Theory For Linear Pi Systems 344     12.3  Molecular Orbital Theory For Cyclic Conjugated PI Systems 348     12.4  Perturbation Of The HOMO And LUMO 351     12.5  Delocalization Of Sigma Electrons (Supplemental) 352     12.6  Concerted Pericyclic Cycloaddition Reactions 353     12.7  Concerted Pericyclic Electrocyclic Reactions 357     12.8  Concerted Pericyclic Sigmatropic Rearrangements 359     12.9  Pericyclic Reactions Summary 361      APPENDIX (A COLLECTION OF IMPORTANT TOOLS)  364      General Bibliography 364     Abbreviations Used in This Text 365     Functional Group Glossary 366     Composite pKa Chart 369     Bond Strength Table 372     Generic Classification Guide 373     Flow Charts for the Classification of Electron Sources and Sinks 375     Pathway Summary 375     Trends Guide 380     Major Routes Summary 384     Major Decisions Guide 388     Thermodynamics and Kinetics 390     Generation of Alternate Paths, Reaction Cubes 390     Organic Structure Elucidation Strategies 393     Notes on Nomenclature 399     HINTS TO PROBLEMS FROM CHAPTERS 8, 9, AND 10 404      INDEX 407

"The revised 2nd edition builds on and improves this legacy, continuing the rigorous mechanistic approach to organic chemistry. Each mechanistic process is divided into its basic units, the dozen common electron flow pathways that become the building blocks of all the common mechanistic processes"-- Provided by publisher

Electron flow in organic chemistry : a decision-based guide to organic mechanisms