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March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th Edition

ISBN: 978-0-470-46259-1
2080 pages
April 2013


The new, revised and updated 7th edition of March’s Advanced Organic Chemistry 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.

The 7th edition proves again it is a must-have desktop reference and textbook for every student and professional working in organic chemistry or related fields.

Key features of the 7th edition:

  • Every chapter has been updated with the most recent reaction information with references to both the primary and review literature
  • New to the 7th edition: 5,500 references since the last edition, updates / rewrites of the retained sections, and an updated index in Appendix B
  • Contains more than 1650 reactions and 20,000 valuable references to the primary literature
  • Includes appendices on the literature of organic chemistry and the classification of reactions according to the compounds synthesized
  • Guides the reader on planning and execution of multi-step synthetic reactions, with detailed descriptions of all the reactions. 

Reviews of the previous edition:

"...a favorite general organic chemistry text and an easy-to-use one-volume reference. We are confident that this book will remain a dominant reference and that it will reside on many chemists' personal bookshelves." –Journal of Medicinal Chemistry

"Who can hope to be seriously accepted as a member of the organic chemistry community without being in possession of at least one edition of 'March'?" –Chemistry and Industry

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Table of Contents





1. Localized Chemical Bonding 3

1.A. Covalent Bonding 3

1.B. Multiple Valence 6

1.C. Hybridization 7

1.D. Multiple Bonds 9

1.E. Photoelectron Spectroscopy 11

1.F. Electronic Structures of Molecules 14

1.G. Electronegativity 15

1.H. Dipole Moment 18

1.I. Inductive and Field Effects 19

1.J. Bond Distances 21

1.K. Bond Angles 25

1.L. Bond Energies 27

2. Delocalized Chemical Bonding 31

2.A. Molecular Orbitals 32

2.B. Bond Energies and Distances in Compounds Containing Delocalized Bonds 35

2.C. Molecules that have Delocalized Bonds 37

2.D. Cross-Conjugation 42

2.E. The Rules of Resonance 43

2.F. The Resonance Effect 45

2.G. Steric Inhibition of Resonance and the Influences of Strain 46

2.H. pp-dp Bonding. Ylids 49

2.I. Aromaticity 50

2.J. Alternant and Nonalternant Hydrocarbons 63

2.K. Aromatic Systems with Electron Numbers other than Six 65

2.L. Other Aromatic Compounds 82

2.M. Hyperconjugation 85

2.N. Tautomerism 89

3. Bonding Weaker Than Covalent 96

3.A. Hydrogen Bonding 96

3.B. p-p Interactions 103

3.C. Addition Compounds 104

3.D. Catenanes and Rotaxanes 118

3.E. Cucurbit[n]Uril-Based Gyroscane 121

4. Stereochemistry and Conformation 122

4.A. Optical Activity and Chirality 122

4.B. What Kinds of Molecules Display Optical Activity? 125

4.C. The Fischer Projection 136

4.D. Absolute Configuration 137

4.E. The Cause of Optical Activity 145

4.F. Molecules with more than One Stereogenic Center 146

4.G. Asymmetric Synthesis 149

4.H. Methods of Resolution 154

4.I. Optical Purity 160

4.J. cis–trans Isomerism 162

4.K. Out-In Isomerism 168

4.L. Enantiotopic and Diastereotopic Atoms, Groups, and Faces 170

4.M. Stereospecific and Stereoselective Syntheses 173

4.N. Conformational Analysis 173

4.O. Molecular Mechanics 190

4.P. STRAIN 192

5. Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes 208

5.A. Carbocations 208

5.B. Carbanions 221

5.C. Free Radicals 234

5.D. Carbenes 249

5.E. Nitrenes 257

6. Mechanisms and Methods of Determining them 261

6.A. Types of Mechanism 261

6.B. Types of Reaction 262

6.C. Thermodynamic Requirements for Reaction 264

6.D. Kinetic Requirements for Reaction 266

6.E. The Baldwin Rules for Ring Closure 270

6.F. Kinetic and Thermodynamic Control 271

6.G. The Hammond Postulate 272

6.H. Microscopic Reversibility 273

6.I. Marcus Theory 273

6.J. Methods of Determining Mechanisms 275

7. Irradiation Processes in Organic Chemistry 289

7.A. Photochemistry 289

7.B. Sonochemistry 307

7.C. Microwave Chemistry 309

8. Acids and Bases 312

8.A. Brønsted Theory 312

8.B. The Mechanism of Proton-Transfer Reactions 323

8.C. Measurements of Solvent Acidity 324

8.D. Acid and Base Catalysis 327

8.E. Lewis Acids and Bases 330

8.F. The Effects of Structure on the Strengths of Acids and Bases 334

8.G. The Effects of the Medium on Acid and Base Strength 343

9. Effects of Structure and Medium on Reactivity 347

9.A. Resonance and Field Effects 347

9.B. Steric Effects 349

9.C. Quantitative Treatments of the Effect of Structure on Reactivity 352

9.D. Effect of Medium on Reactivity and Rate 361


10. Aliphatic Substitution, Nucleophilic and Organometallic 373

10.A. Mechanisms 373

10.B. SET Mechanisms 389

10.C. The Neighboring-Group Mechanism 391

10.D. The SNi Mechanism 408

10.E. Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements 409

10.F. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 413

10.G. Reactivity 417

10.H. Reactions 451

11. Aromatic Substitution, Electrophilic 569

11.A. Mechanisms 569

11.B. Orientation and Reactivity 576

11.C. Quantitative Treatments of Reactivity in the Substrate 586

11.D.A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship 588

11.E. The Effect of the Leaving Group 591

11.F. Reactions 591

12. Aliphatic, Alkenyl, and Alkynyl Substitution, Electrophilic and Organometallic 649

12.A. Mechanisms 650

12.B. Reactivity 658

12.C. Reactions 660

13. Aromatic Substitution: Nucleophilic and Organometallic 732

13.A. Mechanisms 732

13.B. Reactivity 741

13.C. Reactions 745

14. Substitution Reactions: Radical 803

14.A. Mechanisms 803

14.B. Reactivity 812

14.C. Reactions 821

15. Addition to Carbon-Carbon Multiple Bonds 859

15.A. Mechanisms 859

15.B. Orientation and Reactivity 871

15.C. Reactions 881

16. Addition to Carbon-Hetero Multiple Bonds 1067

16.A. Mechanism and Reactivity 1067

16.B. Reactions 1075

17. Eliminations 1253

17.A. Mechanisms and Orientation 1253

17.B. Regiochemistry of the Double Bond 1269

17.C. Stereochemistry of the Double Bond 1273

17.D. Reactivity 1274

17.E. Mechanisms and Orientation in Pyrolytic Eliminations 1278

17.F. Reactions 1282

18. Rearrangements 1321

18.A. Mechanisms 1322

18.B. Longer Nucleophilic Rearrangements 1331

18.C. Free Radical Rearrangements 1333

18.D. Carbene Rearrangements 1337

18.E. Electrophilic Rearrangements 1337

18.F. Reactions 1337

19. Oxidations and Reductions 1433

19.A. Mechanisms 1434

19.B. Reactions 1436






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Author Information

MICHAEL B. SMITH, PhD, is Professor in the Department of Chemistry at the University of Connecticut. He is a coauthor of the fifth and sixth editions of March's Advanced Organic Chemistry and the author of Volumes 6 - 12 of the Compendium of Organic Synthetic Methods (Wiley) as well as several other monographs.
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I recommend this book for students of ecology and plant physiology, although it would be a crime to exclude other disciplines because the authors explanations of how biochemistry makes ecology work are fascinating. (Ecology, 1 December 2015)
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