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Diese überarbeitete und aktualisierte Ausgabe von March's Advanced Organic Chemistry erklärt die Theorien der organischen Chemie anhand von Beispielen und Reaktionen. Planung und Ausführung von mehrstufigen synthetischen Reaktionen werden ausführlich erläutert. Auch die 8. Auflage ist ein Muss für Studenten und Praktiker der organischen Chemie und verwandter Disziplinen.
List of contents
New Reaction Sections Correlation: 7th Edition --> 8th Edition xv
Preface xxi
Common Abbreviations xxv
Biographical Statement xxxi
New Features of the 8th Edition xxxiii
Part I Introduction 1
1. Localized Chemical Bonding 3
1.A. Covalent Bonding 3
1.B. Multiple Valence 7
1.C. Hybridization 7
1.D. Multiple Bonds 9
1.E. Photoelectron Spectroscopy 12
1.F. Electronic Structures of Molecules 15
1.G. Electronegativity 17
1.H. Dipole Moment 19
1.I. Inductive and Field Effects 20
1.J. Bond Distances 23
1.K. Bond Angles 27
1.L. Bond Energies 29
2. Delocalized Chemical Bonding 33
2.A. Molecular Orbitals 34
2.B. Bond Energies and Distances in Compounds Containing Delocalized Bonds 37
2.C. Molecules that have Delocalized Bonds 39
2.D. Cross Conjugation 44
2.E. The Rules of Resonance 46
2.F. The Resonance Effect 48
2.G. Steric Inhibition of Resonance and the Influences of Strain 48
2.H. ppi-dpi Bonding: Ylids 52
2.I. Aromaticity 54
2.I.i. Six-Membered Rings 58
2.I.ii. Five-, Seven-, and Eight-Membered Rings 62
2.I.iii. Other Systems Containing Aromatic Sextets 67
2.J. Alternant and Nonalternant Hydrocarbons 68
2.K. Aromatic Systems with Electron Numbers Other Than Six 70
2.K.i. Systems of Two Electrons 72
2.K.ii. Systems of Four Electrons: Antiaromaticity 73
2.K.iii. Systems of Eight Electrons 76
2.K.iv. Systems of Ten Electrons 77
2.K.v. Systems of More than Ten Electrons: 4n + 2 Electrons 80
2.K.vi. Systems of More Than Ten Electrons: 4n Electrons 85
2.L. Other Aromatic Compounds 89
2.M. Hyperconjugation 92
2.N. Tautomerism 96
2.N.i. Keto-Enol Tautomerism 97
2.N.ii. Other Proton-Shift Tautomerism 100
3. Bonding Weaker Than Covalent 105
3.A. Hydrogen Bonding 105
3.B. pi-pi Interactions 113
3.C. Addition Compounds 114
3.C.i. Electron Donor-Acceptor (EDA) Complexes 114
3.C.ii. Crown Ether Complexes and Cryptates 117
3.C.iii. Inclusion Compounds 122
3.C.iv. Cyclodextrins 125
3.D. Catenanes and Rotaxanes 127
3.E. Cucurbit[n]Uril-Based Gyroscane 131
4. Stereochemistry and Conformation 133
4.A. Optical Activity and Chirality 133
4.B. Dependence of Rotation on Conditions of Measurement 135
4.C. What Kinds of Molecules Display Optical Activity? 136
4.D. The Fischer Projection 147
4.E. Absolute Configuration 148
4.E.i. The Cahn-Ingold-Prelog System 150
4.E.ii. Methods of Determining Configuration 152
4.F. The Cause of Optical Activity 156
4.G. Molecules with More Than One Stereogenic Center 157
4.H. Asymmetric Synthesis 161
4.I. Methods of Resolution 166
4.J. Optical Purity 173
4.K. Cis-Trans Isomerism 175
4.K.i. Cis-Trans Isomerism Resulting from Double Bonds 175
4.K.ii. Cis-Trans Isomerism of Monocyclic Compounds 179
4.K.iii. Cis-Trans Isomerism of Fused and Bridged Ring Systems 180
4.L. Out-In Isomerism 181
4.M. Enantiotopic and Diastereotopic Atoms, Groups, and Faces 183
4.N. Stereospecific and Stereoselective Syntheses 186
4.O. Conformational Analysis 187
4.O.i. Conformation in Open-Chain Systems 188
4.O.ii. Conformation in Six-Membered Rings 194
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About the author
MICHAEL B. SMITH, PHD, is Professor Emeritus in the Department of Chemistry at the University of Connecticut. He is a coauthor of the fifth through seventh editions of
March's Advanced Organic Chemistry and the author of Volumes 6 - 13 of the
Compendium of Organic Synthetic Methods, as well as several other monographs and textbooks.
Summary
Diese überarbeitete und aktualisierte Ausgabe von March's Advanced Organic Chemistry erklärt die Theorien der organischen Chemie anhand von Beispielen und Reaktionen. Planung und Ausführung von mehrstufigen synthetischen Reaktionen werden ausführlich erläutert. Auch die 8. Auflage ist ein Muss für Studenten und Praktiker der organischen Chemie und verwandter Disziplinen.
