Free Download Writing Reaction Mechanisms in Organic Chemistry by Audrey Miller 2nd Ed

2nd Ed

Authors of: Writing Reaction Mechanisms in Organic Chemistry by Audrey Miller 2nd Ed

Audrey Miller

Philippa H. Solomon

Table of Contents in Writing Reaction Mechanisms in Organic Chemistry by Audrey Miller 2nd Ed

Preface to the Second Edition

Preface to First Edition

1  Introduction: Molecular Structure and Reactivity

1. How to Write Lewis Structures and Calculate Formal Charges

A. Determining the Number of Bonds

B. Determining the Number of Rings and/or [pi] Bonds

(Degree of Unsaturation

C. Drawing the Lewis Structure

D. Formal Charge  

2. Representations of Organic Compounds

3. Geometry and Hybridization

4. Electronegativities and Dipoles

5. Resonance Structures

A. Drawing Resonance Structures

B. Rules for Resonance Structures

6. Aromaticity and Antiaromaticity

A. Aromatic Carbocycles

B. Aromatic Heterocycles

C. Antiaromaticity

7. Tautomers and Equilibrium

8. Acidity and Basicity

9. Nucleophiles and Electrophiles

A. Nucleophilicity

B. Substrate

C. Solvent

2 General Principles for Writing Reaction Mechanisms

1. Balancing Equations

2. Using Arrows to Show Moving Electrons

3. Mechanisms in Acidic and Basic Media

4. Electron-Rich Species: Bases or Nucleophiles?

5. Trimolecular Steps

6. Stability of Intermediates

7. Driving Forces for Reactions

A. Leaving Groups 83

B. Formation of a Small Stable Molecule

8.Structural Relationships between Starting Materials and Products

9. Solvent Effects

10. A Last Word

3 Reactions of Nucleophiles and Bases

1. Nucleophilic Substitution

2. Eliminations at Saturated Carbon

3. Nucleophilic Addition to Carbonyl Compounds

4. Base-Promoted Rearrangements

A. The Favorskii Rearrangement

B. The Benzilic Acid Rearrangement

5. Additional Mechanisms in Basic Media

4 Reactions Involving Acids and Other Electrophiles

1. Stability of Carbocations

2. Formation of Carbocations  

3. The Fate of Carbocations

4. Rearrangement of Carbocations

A. The Dienone-Phenol Rearrangement

B. The Pinacol Rearrangement

5. Electrophilic Addition

A. Regiospecificity

B. Stereochemistry

6. Acid-Catalyzed Reactions of Carbonyl Compounds

A. Hydrolysis of Carboxylic Acid Derivatives

B. Hydrolysis and Formation of Acetals and Orthoesters

C. 1,4-Addition

7. Electrophilic Aromatic Substitution

8. Carbenes

A. Singlet and Triplet Carbenes

B. Formation of Carbenes

C. Reactions of Carbenes

9. Electrophilic Heteroatoms

A. Electron-Deficient Nitrogen

B. Rearrangements Involving Electrophilic Nitrogen

C. Rearrangement Involving Electron-Deficient Oxygen

5 Radicals and Radical Anions

1. Introduction

2. Formation of Radicals

A. Homolytic Bond Cleavage

B. Hydrogen Abstraction from Organic Molecules

C. Organic Radicals Derived from Functional Groups

3. Radical Chain Processes

4. Radical Inhibitors

5. Determining the Thermodynamic Feasibility of Radical Reactions

6. Addition of Radicals

A. Intermolecular Radical Addition

B. Intramolecular Radical Addition: Radical Cyclization Reactions

7. Fragmentation Reactions

A. Loss of CO[subscript 2]

B. Loss of a Ketone

C. Loss of N[subscript 2]

D. Loss of CO

8. Rearrangement of Radicals

9. The S[subscript RN] 1 Reaction

10. The Birch Reduction

11. A Radical Mechanism for the Rearrangement of Some Anions

6 Pericyclic Reactions

1. Introduction

A. Types of Pericyclic Reactions

B. Theories of Pericyclic Reactions

2. Electrocyclic Reactions

A. Selection Rules for Electrocyclic Reactions

B. Stereochemistry of Electrocyclic Reactions (Conrotatory and Disrotatory Processes)

C. Electrocyclic Reactions of Charged Species (Cyclopropyl Cations)

3. Cycloadditions

A. Terminology of Cycloadditions

B. Selection Rules for Cycloadditions

C. Secondary Interactions

D. Cycloadditions of Charged Species

4. Sigmatropic Rearrangements

5. The Ene Reaction

6. A Molecular Orbital View of Pericyclic Processes  

7. Additional Problems

Appendix A Lewis Structures of Common Functional Groups

Appendix B Symbols and Abbreviations Used in Chemical Notation

Appendix C

Relative Acidities of Common Organic and Inorganic Substances

Index

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