Writing organic reaction mechanisms: a practical guide
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
London
Taylor & Francis
1994
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | 2. Aufl. u.d.T.: Edenborough, Michael: Organic reaction mechanisms |
| Beschreibung: | XI, 420 S. graph. Darst. |
| ISBN: | 0748401717 |
Internformat
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Datensatz im Suchindex
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| adam_text | WRITING ORGANIC REACTION MECHANISMS: A PRACTICAL GUIDE BY MICHAEL
EDENBOROUGH TAYLOR &FRANCIS PTTBLISHEVS SINCE 1798 CONTENTS CONTENTS V
PREFACE XI PART I: BASIC PRINCIPLES 1 INTRODUCTION 1 1.1 THE AIM OF THIS
BOOK 1 1.2 WHAT IS ORGANIC CHEMISTRY? 2 1.3 ORGANIC SYNTHESIS 3 1.4 THE
NEED FOR MECHANISMS 3 1.5 EXAMPLES 4 1.6 HOW TO USE THIS BOOK 7 2
ELECTRON COUNTING 9 2.1 INTRODUCTION 9 2.2 ATOMS 9 2.3 UNCHARGED
MOLECULES 14 2.4 MOLECULES WITH WHOLE CHARGES 17 3 COVALENT BONDING AND
POLARIZATION 27 3.1 INTRODUCTION 27 3.2 PARTIALLY CHARGED SPECIES 27 3.3
BOND FISSION 31 3.4 ISOLATED MULTIPLE BONDS 33 3.5 CONJUGATED MULTIPLE
BONDS 37 4 SHAPE OF MOLECULES 41 4.1 INTRODUCTION 41 4.2 TYPES OF
BONDING 41 4.3 TETRAHEDRAL GEOMETRY 44 4.4 TRIGONAL PLANAR GEOMETRY 49
4.5 LINEAR GEOMETRY 54 4.6 FURTHER EXAMPLES 56 5 STABILIZATION OF
CHARGED SPECIES 63 5.1 INTRODUCTION 63 V 5.2 INDUCTIVE EFFECTS 64 5.2.1
CHARGED HYDROCARBON SPECIES 64 5.2.2 CHARGED NON-HYDROCARBON SPECIES 68
5.3 MESOMERIC EFFECTS 69 5.3.1 CHARGED HYDROCARBON SPECIES 69 5.3.2
CHARGED NON-HYDROCARBON SPECIES 71 5.4 DEGREE OF S ORBITAL CHARACTER 75
5.5 D ORBITAL INVOLVEMENT 76 5.6 AROMATIC CHARACTER 77 5.7 HYDROGEN
BONDING 80 5.8 STERIC EFFECTS 82 6 THERMODYNAMIC AND KINETIC EFFECTS 85
6.1 INTRODUCTION 85 6.2 THERMODYNAMIC CONSIDERATIONS 87 6.3 KINETIC
CONSIDERATIONS 91 6.4 CATALYSIS 96 6.4.1 GENERAL CONSIDERATIONS 96 6.4.2
ACID/BASE CATALYSIS 97 7 ACID/BASE CHARACTERISTICS 99 7.1 INTRODUCTION
99 7.2 DEFINITIONS OF ACIDS AND BASES 99 7.2.1 ARRHENIUS 100 7.2.2
BROENSTED-LOWRY 100 7.2.3 LEWIS 106 7.2.4 CADY-ELSEY 107 7.3
ELECTROPHILIC AND NUCLEOPHILIC PROPERTIES 108 7.4 EXTERNAL EFFECTS 112
PART II: MECHANISMS 8 INTRODUCTION 117 9 NUCLEOPHILIC SUBSTITUTION
REACTIONS 119 9.1 INTRODUCTION 119 9.2 SUBSTITUTION AT A SATURATED
CARBON 120 9.2.1 INTRODUCTION 120 9.2.2 UNIMOLECULAR SUBSTITUTION 121
9.2.3 BIMOLECULAR SUBSTITUTION 126 9.2.4 INTRAMOLECULAR SUBSTITUTION 131
9.2.5 FORMATION AND CLEAVAGE OF THREE MEMBERED RINGS 134 9.3
SUBSTITUTION AT AN UNSATURATED CARBON 136 9.3.1 SNI AND SN2 MECHANISMS
136 VI 9.3.2 TETRAHEDRAL MECHANISM 138 9.3.3 ESTER HYDROLYSIS 139 9.4
TRIGONAL BIPYRAMIDAL SUBSTITUTION 142 10 ELECTROPHILIC SUBSTITUTION
REACTIONS 145 10.1 INTRODUCTION 145 10.2 AROMATIC SUBSTITUTION 146
10.2.1 ARENIUM ION MECHANISM 146 10.2.2 ORIENTATION AND REACTIVITY 150
10.2.3 ORTHOJPARA RATIO 153 10.2.4 MULTIPLE SUBSTITUTIONS 154 10.3
ALIPHATIC SUBSTITUTION 156 11 RADICAL SUBSTITUTION REACTIONS 161 11.1
INTRODUCTION 161 11.2 PHOTOCHLORINATION OF METHANE 161 11.3 REACTIVITY
AND STRUCTURE 165 11.4 NEIGHBOURING GROUP ASSISTANCE 168 11.5 FURTHER
EXAMPLES OF RADICAL REACTIONS 170 12 ADDITION REACTIONS TO CARBON/CARBON
MULTIPLE BONDS 177 12.1 INTRODUCTION 177 12.2 CYCLIC ADDITION 179 12.2.1
HETEROGENEOUS CATALYTIC HYDROGENATION 179 12.2.2 OTHER SYN-ADDITIONS 180
12.2.3 PERICYCLIC REACTIONS 182 12.3 ELECTROPHILIC ADDITION 185 12.3.1
THE ADDITION OF A SYMMETRICAL MOLECULE 185 12.3.2 THE RATE OF ADDITION
192 12.3.3 ORIENTATION OF ADDITION 193 12.3.4 SOME OTHER ELECTROPHILIC
ADDITIONS 196 12.4 RADICAL ADDITION 199 12.5 NUCLEOPHILIC ADDITION 200
12.6 CONJUGATED ADDITION 201 13 ADDITION REACTIONS TO CARBON/OXYGEN
DOUBLE BONDS 205 13.1 INTRODUCTION 205 13.2 STRUCTURE AND REACTIVITY 205
13.3 HYDRATION 208 13.4 OTHER ADDITION REACTIONS 211 13.5 ADDITION OF
CARBON ANIONS 213 13.5.1 CYANIDE, ACETYLENE AND ALKYL ANIONS 213 13.5.2
CARBONYL STABILIZED ANIONS 216 13.6 STEREOCHEMICAL CONSEQUENCES 223 13.7
CONJ UGATED ADDITION 224 VLL 14 ELIMINATION REACTIONS 227 14.1
INTRODUCTION 227 14.2 BIMOLECULAR 1,2-ELIMINATION REACTIONS 228 14.2.1
ANTI- ELIMINATION 228 14.2.2 SYRT-ELIMINATION 236 14.3 UNIMOLECULAR
1,2-ELIMINATION REACTIONS 237 14.4 1,1-ELIMINATION REACTIONS 242 14.5
PYROLYTIC ELIMINATION REACTIONS 243 15 SEQUENTIAL ADDITIONIELIMINATION
REACTIONS 249 15.1 INTRODUCTION 249 15.2 ADDITION/ELIMINATION REACTIONS
249 15.3 ELIMINATION/ADDITION REACTIONS 255 16 REARRANGEMENT AND
FRAGMENTATION REACTIONS 259 16.1 INTRODUCTION 259 16.2 CARBON/CARBON
REARRANGEMENTS 259 16.3 CARBON/NITROGEN REARRANGEMENTS 266 16.4
CARBON/OXYGEN REARRANGEMENTS 269 16.5 FRAGMENTATION REACTIONS 270 17
REDOX REACTIONS 273 17.1 INTRODUCTION 273 17.2 REDUCTION REACTIONS 274
17.2.1 ELECTRON DONORS 274 17.2.2 HYDRIDE ION DONORS 278 17.3 OXIDATION
REACTIONS 280 17.4 DISPROPORTIONATION REACTIONS 284 PART III: APPENDICES
18 GLOSSARY 289 19 ABBREVIATIONS 353 19.1 ATOMIC, GROUP AND MOLECULAR
ABBREVIATION 353 19.2 MECHANISTIC ABBREVIATIONS 355 19.3 REACTION TYPE
ABBREVIATIONS 356 20 MOLECULAR NOTATIONS 359 20.1 NON-STRUCTURAL
NOTATIONS 359 20.1.1 EMPIRICAL FORMULAE 359 20.1.2 MOLECULAR FORMULAE
359 20.2 TWO DIMENSIONAL STRUCTURAL NOTATIONS 360 20.2.1 DOT AND CROSS
360 20.2.2 LINE NOTATION 361 VM 20.2.3 EXPANDED LINE NOTATION 362 20.2.4
STICK NOTATION 362 20.2.5 TWO DIMENSIONAL SKELETAL NOTATION 363 20.3
THREE DIMENSIONAL STRUCTURAL NOTATIONS 365 20.3.1 HAWORTH NOTATION 365
20.3.2 THREE DIMENSIONAL SKELETAL NOTATION 366 20.3.3 STEREO PROJECTION
366 20.3.4 SAWHORSE PROJECTION 367 20.3.5 NEWMANN PROJECTION 368 20.3.6
FISCHER PROJECTION 368 21 STEREOCHEMICAL TERMINOLOGY 369 21.1
INTRODUCTION 369 21.2 STRUCTURAL ISOMERISM 370 21.2.1 SKELETAL ISOMERISM
371 21.2.2 POSITIONAL ISOMERISM 372 21.2.3 FUNCTIONAL ISOMERISM 374
21.2.4 TAUTOMERIC ISOMERISM 375 21.2.5 META ISOMERISM 375 21.3
STEREOISOMERISM 376 21.3.1 OPTICAL ISOMERISM 378 21.3.2 GEOMETRICAL
ISOMERISM 383 21.3.3 CONFORMERS 386 22 OXIDATION NUMBERS 391 22.1
INTRODUCTION 391 22.2 OXIDATION NUMBERS IN IONIC SPECIES 391 22.3
OXIDATION NUMBERS IN COVALENT SPECIES 393 23 SKELETAL INDEX 397 23.1
HYDROCARBON COMPOUNDS 397 23.2 OXYGEN CONTAINING COMPOUNDS 402 23.3
NITROGEN CONTAINING COMPOUNDS 408 23.4 NITROGEN AND OXYGEN CONTAINING
COMPOUNDS 413 23.5 SULFUR CONTAINING COMPOUNDS 417 23.6 PHOSPHORUS
CONTAINING COMPOUNDS 419
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| spelling | Edenborough, Michael Verfasser aut Writing organic reaction mechanisms a practical guide by Michael Edenborough London Taylor & Francis 1994 XI, 420 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier 2. Aufl. u.d.T.: Edenborough, Michael: Organic reaction mechanisms Chemistry, Organic Organic reaction mechanisms Reaktionsmechanismus (DE-588)4177123-0 gnd rswk-swf Organische Chemie (DE-588)4043793-0 gnd rswk-swf Reaktionsmechanismus (DE-588)4177123-0 s Organische Chemie (DE-588)4043793-0 s DE-604 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006448166&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Edenborough, Michael Writing organic reaction mechanisms a practical guide Chemistry, Organic Organic reaction mechanisms Reaktionsmechanismus (DE-588)4177123-0 gnd Organische Chemie (DE-588)4043793-0 gnd |
| subject_GND | (DE-588)4177123-0 (DE-588)4043793-0 |
| title | Writing organic reaction mechanisms a practical guide |
| title_auth | Writing organic reaction mechanisms a practical guide |
| title_exact_search | Writing organic reaction mechanisms a practical guide |
| title_full | Writing organic reaction mechanisms a practical guide by Michael Edenborough |
| title_fullStr | Writing organic reaction mechanisms a practical guide by Michael Edenborough |
| title_full_unstemmed | Writing organic reaction mechanisms a practical guide by Michael Edenborough |
| title_short | Writing organic reaction mechanisms |
| title_sort | writing organic reaction mechanisms a practical guide |
| title_sub | a practical guide |
| topic | Chemistry, Organic Organic reaction mechanisms Reaktionsmechanismus (DE-588)4177123-0 gnd Organische Chemie (DE-588)4043793-0 gnd |
| topic_facet | Chemistry, Organic Organic reaction mechanisms Reaktionsmechanismus Organische Chemie |
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