Writing Reaction Mechanisms in Organic Chemistry -  Philippa H. Solomon

Writing Reaction Mechanisms in Organic Chemistry (eBook)

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1999 | 2. Auflage
471 Seiten
Elsevier Science (Verlag)
978-0-08-052133-6 (ISBN)
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Writing Reaction Mechanisms in Organic Chemistry, Second Edition, is an invaluable guide to charting the movements of atoms and electrons in the reactions of organic molecules. Miller and Solomon illustrate that understanding organic reactions is based on applying general principles rather than the rote memorization of unrelated processes, and, in turn, emphasize that writing mechanisms is a practical method of applying knowledge of previously encountered reactions and reaction conditions to new reactions. Students and research chemists alike will find this book useful in providing a method of organizing and synthesizing an oftentimes overwhelming quantity of information into a set of general principles and guidelines for determining and describing organic reaction mechanisms.


* Essential for those students who need to have mechanisms explained in greater detail than most organic chemistry textbooks provide.
* Illustrated with hundreds of chemical structures
* Extensively rewritten and reorganized to make the presentation and format even easier for students to use
* Contains many problem sets and answers to all problems to help students work through general principles and applications
* Appendixes have been added to this edition that contain easily referenced information on Lewis structures, symbols for chemical notation, and the relative acidities of common substances
Writing Reaction Mechanisms in Organic Chemistry, Second Edition, is an invaluable guide to charting the movements of atoms and electrons in the reactions of organic molecules. Miller and Solomon illustrate that understanding organic reactions is based on applying general principles rather than the rote memorization of unrelated processes, and, in turn, emphasize that writing mechanisms is a practical method of applying knowledge of previously encountered reactions and reaction conditions to new reactions. Students and research chemists alike will find this book useful in providing a method of organizing and synthesizing an oftentimes overwhelming quantity of information into a set of general principles and guidelines for determining and describing organic reaction mechanisms. - llustrated with hundreds of chemical structures, all redrawn from the first edition, with addedemphasis on three-dimensional structures and stereochemical aspects of reaction mechanisms- Extensively rewritten and reorganized to make the presentation and format more accessible to first-year organic chemistry students, as well as advanced undergraduate and graduate students- Chapter 6 is completely revised to streamline the treatment of pericyclic reactions, while introducing the principles underlying the symmetry operations and orbital correlation diagrams- New appendixes in this edition contain easily referenced information on Lewis structures, chemical symbols and notation, and relative acidities of common functional groups

Cover 1
Writing Reaction Mechanisms in Organic Chemistry 4
Copyright Page 5
Contents 6
Preface to the Second Edition 12
Preface to First Edition 14
Chapter 1. Introduction–Molecular Structure and Reactivity 16
1. How to Write Lewis Structures and Calculate Formal Charges 17
2. Representations of Organic Compounds 27
3. Geometry and Hybridization 29
4. Electronegativities and Dipoles 31
5. Resonance Structures 33
6. Aromaticity and Antiaromaticity 41
7. Tautomers and Equilibrium 44
8. Acidity and Basicity 47
9. Nucleophiles and Electrophiles 52
Chapter 2. General Principles for Writing Reaction Mechanisms 78
1. Balancing Equations 79
2. Using Arrows to Show Moving Electrons 81
3. Mechanisms in Acidic and Basic Media 84
4. Electron-Rich Species: Bases or Nucleophiles? 91
5. Trimolecular Steps 93
6. Stability of Intermediates 94
7. Driving Forces for Reactions 97
8. Structural Relationships between Starting Materials and Products 100
9. Solvent Effects 101
10. A Last Word 103
Chapter 3. Reactions of Nucleophiles and Bases 120
1. Nucleophilic Substitution 121
2. Eliminations at Saturated Carbon 135
3. Nucleophilic Addition to Carbonyl Compounds 138
4. Base-Promoted Rearrangements 156
5. Additional Mechanisms in Basic Media 159
Chapter 4. Reactions Involving Acids and Other Electrophiles 210
1. Stability of Carbocations 210
2. Formation of Carbocations 211
3. The Fate of Carbocations 214
4. Rearrangement of Carbocations 215
5. Electrophilic Addition 223
6. Acid-Catalyzed Reactions of Carbonyl Compounds 228
7. Electrophilic Aromatic Substitution 235
8. Carbenes 239
9. Electrophilic Heteroatoms 246
Chapter 5. Radicals and Radical Anions 298
1. Introduction 298
2. Formation of Radicals 299
3. Radical Chain Processes 302
4. Radical Inhibitors 305
5. Determining the Thermodynamic Feasibility of Radical Reactions 307
6. Addition of Radicals 309
7. Fragmentation Reactions 314
8. Rearrangement of Radicals 318
9. The Srnl Reaction 322
10. The Birch Reduction 325
11. A Radical Mechanism for the Rearrangement of Some Anions 327
Chapter 6. Pericyclic Reactions 358
1. Introduction 358
2. Electrocyclic Reactions 361
3. Cycloadditions 370
4. Sigmatropic Rearrangements 381
5. The Ene Reaction 388
6. A Molecular Orbital View of Pericyclic Processes 394
Chapter 7. Additional Problems 432
Appendix A: Lewis Structures of Common Functional Groups 468
Appendix B: Symbols and Abbreviations Used in Chemical Notation 470
Appendix C: Relative Acidities of Common Organic and Inorganic Substances 472
Index 480

Erscheint lt. Verlag 17.11.1999
Sprache englisch
Themenwelt Naturwissenschaften Chemie Organische Chemie
Naturwissenschaften Chemie Technische Chemie
Technik Umwelttechnik / Biotechnologie
ISBN-10 0-08-052133-9 / 0080521339
ISBN-13 978-0-08-052133-6 / 9780080521336
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