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March'S Advanced Organic Chemistry : Reactions, Mechanisms, And Structure

March'S Advanced Organic Chemistry : Reactions, Mechanisms, And Structure

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About the Book

The new, revised and updated edition clearly explains the theories and examples of organic chemistry, providing the most comprehensive resource about organic chemistry available. Readers are guided on planning and execution of multi-step synthetic reactions, with detailed descriptions of all the reactions. The first five chapters deal with the structure of organic compounds and discuss important organic chemistry bonds, fundamental principles of conformation, and stereochemistry of organic molecules and reactive intermediates in organic chemistry. Chapters 6 to 9 are concerned with general principles of mechanism in organic chemistry, including acids and bases, photochemistry, sonochemistry and microwave irradiation and finally the relationship between structure and reactivity. The last 10 chapters cover the nature and the scope of organic reactions and their mechanisms.

·Localized Chemical Bonding
·Delocalized Chemical Bonding
·Bonding Weaker Than Covalent
·Stereochemistry and Conformation
·Carbocations, Carbanions, Free Radicals, Carbenes and Nitrenes
·Mechanisms and Methods of Determining them
·Irradiation Processes in Organic Chemistry
·Acids and Bases
·Effects of Structure and Medium on Reactivity
·Aliphatic Substitution, Nucleophilic and Organometallic
·Aromatic Substitution, Electrophilic
·Aliphatic, Alkenyl and Alkynyl Substitution, Electrophilic and Organometallic
·Aromatic Substitution: Nucleophilic and Organometallic
·Substitution Reactions: Radical
·Addition to Carbon-Carbon Multiple Bonds
·Addition to Carbon-Hetero Multiple Bonds
·Eliminations
·Rearrangements
·Oxidations and Reductions

About the Author

Michael B. Smith is a professor in the Department of Chemistry at the University of Connecticut, Storrs, Connecticut.



Table of Contents:
Preface Common Abbreviations Biographical Statement Part I Introduction 1. Localized Chemical Bonding 1.A. Covalent Bonding 1.B. Multiple Valence 1.C. Hybridization 1.D. Multiple Bonds 1.E. Photoelectron Spectroscopy 1.F. Electronic Structures of Molecules 1.G. Electronegativity 1.H. Dipole Moment 1.I. Inductive and Field Effects 1.J. Bond Distances 1.K. Bond Angles 1.L. Bond Energies 2. Delocalized Chemical Bonding 2.A. Molecular Orbitals 2.B. Bond Energies and Distances in Compounds Containing Delocalized Bonds 2.C. Molecules that have Delocalized Bonds 2.D. Cross-Conjugation 2.E. The Rules of Resonance 2.F. The Resonance Effect 2.G. Steric Inhibition of Resonance and the Influences of Strain 2.H. pp-dp Bonding. Ylids 2.I. Aromaticity 2.J. Alternant and Nonalternant Hydrocarbons 2.K. Aromatic Systems with Electron Numbers other than Six 2.L. Other Aromatic Compounds 2.M. Hyperconjugation 2.N. Tautomerism 3. Bonding Weaker Than Covalent 3.A. Hydrogen Bonding 3.B. p-p Interactions 3.C. Addition Compounds 3.D. Catenanes and Rotaxanes 3.E. Cucurbit[n]Uril-Based Gyroscane 4. Stereochemistry and Conformation 4.A. Optical Activity and Chirality 4.B. What Kinds of Molecules Display Optical Activity? 4.C. The Fischer Projection 4.D. Absolute Configuration 4.E. The Cause of Optical Activity 4.F. Molecules with more than One Stereogenic Center 4.G. Asymmetric Synthesis 4.H. Methods of Resolution 4.I. Optical Purity 4.J. cis--trans Isomerism 4.K. Out-In Isomerism 4.L. Enantiotopic and Diastereotopic Atoms, Groups and Faces 4.M. Stereospecific and Stereoselective Syntheses 4.N. Conformational Analysis 4.O. Molecular Mechanics 4.P. Strain 5. Carbocations, Carbanions, Free Radicals, Carbenes and Nitrenes 5.A. Carbocations 5.B. Carbanions 5.C. Free Radicals 5.D. Carbenes 5.E. Nitrenes 6. Mechanisms and Methods of Determining them 6.A. Types of Mechanism 6.B. Types of Reaction 6.C. Thermodynamic Requirements for Reaction 6.D. Kinetic Requirements for Reaction 6.E. The Baldwin Rules for Ring Closure 6.F. Kinetic and Thermodynamic Control 6.G. The Hammond Postulate 6.H. Microscopic Reversibility 6.I. Marcus Theory 6.J. Methods of Determining Mechanisms 7. Irradiation Processes in Organic Chemistry 7.A. Photochemistry 7.B. Sonochemistry 7.C. Microwave Chemistry 8. Acids and Bases 8.A. Brønsted Theory 8.B. The Mechanism of Proton-Transfer Reactions 8.C. Measurements of Solvent Acidity 8.D. Acid and Base Catalysis 8.E. Lewis Acids and Bases 8.F. The Effects of Structure on the Strengths of Acids and Bases 8.G. The Effects of the Medium on Acid and Base Strength 9. Effects of Structure and Medium on Reactivity 9.A. Resonance and Field Effects 9.B. Steric Effects 9.C. Quantitative Treatments of the Effect of Structure on Reactivity 9.D. Effect of Medium on Reactivity and Rate Part II Introduction 10. Aliphatic Substitution, Nucleophilic and Organometallic 10.A. Mechanisms 10.B. SET Mechanisms 10.C. The Neighboring-Group Mechanism 10.D. The SNi Mechanism 10.E. Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements 10.F. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 10.G. Reactivity 10.H. Reactions 11. Aromatic Substitution, Electrophilic 11.A. Mechanisms 11.B. Orientation and Reactivity 11.C. Quantitative Treatments of Reactivity in the Substrate 11.D.A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship 11.E. The Effect of the Leaving Group 11.F. Reactions 12. Aliphatic, Alkenyl and Alkynyl Substitution, Electrophilic and Organometallic 12.A. Mechanisms 12.B. Reactivity 12.C. Reactions 13. Aromatic Substitution: Nucleophilic and Organometallic 13.A. Mechanisms 13.B. Reactivity 13.C. Reactions 14. Substitution Reactions: Radical 14.A. Mechanisms 14.B. Reactivity 14.C. Reactions 15. Addition to Carbon-Carbon Multiple Bonds 15.A. Mechanisms 15.B. Orientation and Reactivity 15.C. Reactions 16. Addition to Carbon-Hetero Multiple Bonds 16.A. Mechanism and Reactivity 16.B. Reactions 17. Eliminations 17.A. Mechanisms and Orientation 17.B. Regiochemistry of the Double Bond 17.C. Stereochemistry of the Double Bond 17.D. Reactivity 17.E. Mechanisms and Orientation in Pyrolytic Eliminations 17.F. Reactions 18. Rearrangements 18.A. Mechanisms 18.B. Longer Nucleophilic Rearrangements 18.C. Free Radical Rearrangements 18.D. Carbene Rearrangements 18.E. Electrophilic Rearrangements 18.F. Reactions 19. Oxidations and Reductions 19.A. Mechanisms 19.B. Reactions Appendix A: The Literature of Organic Chemistry Appendix B: Classification of Reactions by Type of Compounds Synthesized Indexes Author Index Subject Index


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Product Details
  • ISBN-13: 9788126556588
  • Publisher: Wiley India Pvt Ltd
  • Binding: Paperback
  • Language: English
  • ISBN-10: 8126556587
  • Publisher Date: 2015
  • Edition: 7
  • No of Pages: 2076

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