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Electron flow in organic chemistry (2nd Ed., 2nd Edition) A decision-based guide to organic mechanisms

Langue : Anglais

Auteur :

Couverture de l’ouvrage Electron flow in organic chemistry

With its acclaimed decision-based approach, Electron Flow in Organic Chemistry enables readers to develop the essential critical thinking skills needed to analyze and solve problems in organic chemistry, from the simple to complex. The author breaks down common mechanistic organic processes into their basic units to explain the core electron flow pathways that underlie these processes. Moreover, the text stresses the use of analytical tools such as flow charts, correlation matrices, and energy surfaces to enable readers new to organic chemistry to grasp the fundamentals at a much deeper level.

This Second Edition of Electron Flow in Organic Chemistry has been thoroughly revised, reorganized, and streamlined in response to feedback from both students and instructors. Readers will find more flowcharts, correlation matrices, and algorithms that illustrate key decision-making processes step by step. There are new examples from the field of biochemistry, making the text more relevant to a broader range of readers in chemistry, biology, and medicine. This edition also offers three new chapters:

  • Proton transfer and the principles of stability
  • Important reaction archetypes
  • Qualitative molecular orbital theory and pericyclic reaction

The text's appendix features a variety of helpful tools, including a general bibliography, quick-reference charts and tables, pathway summaries, and a major decisions guide.

With its emphasis on logical processes rather than memorization to solve mechanistic problems, this text gives readers a solid foundation to approach and solve any problem in organic chemistry.

1 BONDING AND ELECTRON DISTRIBUTION

1.1 The Decision-Based Approach To Organic Chemistry   

1.2 Ionic And Covalent Bonding

1.3 Lewis Structures And Resonance Forms

1.4 Curved-Arrow Notation

1.5 Nomenclature And Abbreviations

1.6 An Orbital View Of Bonding (Supplemental)

1.7 The Shapes Of Molecules

1.8 Molecular Repulsions, Attractions, And Hydrogen Bonding

1.9 Conjugation, Vinylogy, Aromaticity

1.10  Summary

2  THE PROCESS OF BOND FORMATION

2.1 Energetics Control Knowledge

2.2 Orbital Overlap In Covalent Bond Formation

2.3 Orbital Interaction Diagrams

2.4 Polarizability And Hard And Soft Acid?Base Theory

2.5 Thermodynamics, Position Of Equilibrium

2.6 Kinetics, Rate Of Reaction

2.7 Solvent Stabilization Of Ions

2.8 Enzymatic Catalysis - Lessons From Biochemistry

2.9 Summary

3  PROTON TRANSFER AND THE PRINCIPLES OF STABILITY

3.1 Introduction To Proton Transfer

3.2 Ranking Of Acids And Bases, The pKa Chart

3.3 Structural Factors That Influence Acid Strength

3.4 Structural Factors That Influence Base Strength

3.5 Carbon Acids & Ranking Of Electron-Withdrawing Groups

3.6 Calculation Of Keq For Proton Transfer

3.7 Proton Transfer Mechanisms

3.8 Common Errors

3.9 Proton Transfer Product Predictions

3.10  Summary

4  IMPORTANT REACTION ARCHETYPES 

4.1 Introduction To Reaction Archetypes

4.2 Nucleophilic Substitution At A Tetrahedral Center

4.3 Elimination Reactions Create Pi Bonds

4.4 Addition Reactions To Polarized Multiple Bonds

4.5 Nucleophilic Substitution At A Trigonal Planar Center

4.6 Electrophilic Substitution At A Trigonal Planar Center

4.7 Rearrangements To An Electrophilic Carbon

4.8 Reaction Archetype Summary

5  CLASSIFICATION OF ELECTRON SOURCES

5.1 Generalized Ranking Of Electron Sources

5.2 Nonbonding Electrons

5.3 Electron-Rich Sigma Bonds

5.4 Electron-Rich Pi Bonds

5.5 Simple Pi Bonds

5.6 Aromatic Rings

5.7 Summary Of Generic Electron Sources

6  CLASSIFICATION OF ELECTRON SINKS

6.1 Generalized Ranking Of Electron Sinks

6.2 Electron-Deficient Species

6.3 Weak Single Bonds

6.4 Polarized Multiple Bonds Without Leaving Groups

6.5 Polarized Multiple Bonds With Leaving Groups

6.6 Summary Of Generic Electron Sinks

7  THE ELECTRON FLOW PATHWAYS 

7.1 The Dozen Most Common Pathways

7.2 Six Minor Pathways

7.3 Common Path Combinations

7.4 Variations On A Theme

7.5 Twelve Major Paths Summary And Crosschecks

8  INTERACTION OF ELECTRON SOURCES AND SINKS

8.1 Source And Sink Correlation Matrix

8.2 H-A Sinks Reacting With Common Sources

8.3 Y?L Sinks Reacting With Common Sources

8.4 sp3 C?L Sinks Reacting With Common Sources

8.5 C=Y Sinks Reacting With Common Sources

8.6 R?C?Y Sinks Reacting With Common Sources

8.7 C=C?Ewg Sinks Reacting With Common Sources

8.8 L?C=Y Sinks Reacting With Common Sources

8.9 Miscellaneous Reactions

8.10  Metal Ions As Electron Sinks

8.11  Rearrangements To An Electrophilic Center

8.12  Nu-L Reactions

8.13  Product Matrix Summary

9  DECISIONS

9.1 Decision Point Recognition

9.2 Multiple Additions

9.3 Regiochemistry & Stereochemistry Of Enolate Formation

9.4 Ambident Nucleophiles

9.5 Substitution Vs. Elimination

9.6 Ambident Electrophiles

9.7 Intermolecular Vs. Intramolecular

9.8 To Migrate Or Not To An Electrophilic Center

9.8 Summary

10 CHOOSING THE MOST PROBABLE PATH 

10.1  Problem-Solving In General

10.2  General Mechanistic Cross-Checks

10.3  The Path-Selection Process

10.4  Reaction Mechanism Strategies

10.5  Worked Mechanism Examples

10.6  Product Prediction Strategies

10.7  Worked Product Prediction Examples

10.8  Methods For Testing Mechanisms

10.9  Lessons from Biochemical Mechanisms

10.10 Summary

11 ONE-ELECTRON PROCESSES

11.1  Radical Structure And Stability

11.2  Radical Path Initiation

11.3  Major Paths For Radicals Reacting With Neutrals

11.4  Unimolecular Radical Paths

11.5  Termination Radical Paths

11.6  Radical Path Combinations

11.7  Approaches To Radical Mechanisms

11.8  Single Electron Transfer, S.E.T., And Charged Radicals

11.9  Dissolving Metal Reductions

11.10 Electron Transfer Initiated Processes

11.11 One-Electron Path Summary

12 QUALITATIVE M.O. THEORY & PERICYCLIC REACTIONS 

12.1  Review Of Orbitals As Standing Waves

12.2  Molecular Orbital Theory For Linear Pi Systems

12.3  Molecular Orbital Theory For Cyclic Conjugated PI Systems

12.4  Perturbation Of The HOMO And LUMO

12.5  Delocalization Of Sigma Electrons (Supplemental)

12.6  Concerted Pericyclic Cycloaddition Reactions

12.7  Concerted Pericyclic Electrocyclic Reactions

12.8  Concerted Pericyclic Sigmatropic Rearrangements

12.9  Pericyclic Reactions Summary

APPENDIX (A COLLECTION OF IMPORTANT TOOLS) 

General Bibliography

Abbreviations Used in This Text

Functional Group Glossary

Composite pKa Chart

Bond Strength Table

Generic Classification Guide

Flow Charts for the Classification of Electron Sources and Sinks

Pathway Summary

Trends Guide

Major Routes Summary

Major Decisions Guide

Thermodynamics and Kinetics

Generation of Alternate Paths, Reaction Cubes

Organic Structure Elucidation Strategies

Notes on Nomenclature

HINTS TO PROBLEMS FROM CHAPTERS 8, 9, AND 10

INDEX

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