Properties and reactions of bonds in organic molecules:
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
London
Longmans
1968
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XIII,556 S.m.Abb.u.Tab. |
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| 245 | 1 | 0 | |a Properties and reactions of bonds in organic molecules |
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Record in the Search Index
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| adam_text | Properties and reactions of bonds
in organic molecules
K F Reid B Sc Ph D
{
•
Longmans
Contents
• Preface xi
1 Introduction and nomenclature of organic compounds 1
1 The scope, of organic chemistry 1
2 Empirical, molecular and structural formulae 3
3 Classification and nomenclature of organic compounds 6
4 Sources of organic compounds „ 20
Problems 21
2 Atomic structures, dimensions and electronegativities 22
1 Some elements of quantum mechanics 22
2 Covalent atomic radii and bond lengths 28
3 Bond polarity and electronegativities 30
3 Chemical bonding in hydrocarbons 35
1 Introduction 35
2 The molecular orbital model 35
3 Directional nature of covalent bonds 39
4 Delocalized orbital s and conjugated systems 47
5 Hybridization and electronegativities 50
4 Stereoisomerism of organic molecules 52
1 Introduction 52
2 Free rotation about carbon—carbon single bonds 53
3 Geometrical isomerism 57
4 Stereoisomerism of cyclic compounds 60
5 Optical isomerism 69
A Introduction 69
B Optical activity in saturated compounds 71
C Relative and absolute configurations 76
D Optical activity in unsaturated and aromatic compounds 79
E Hetero atoms and optical activity « 82
F Racemic forms: resolution and racemization 83
Problems 87
vi Contents
5 Electronic movements in molecules and ions 89
1 Introduction 89
2 Polarization of charge within molecules 89
A The inductive effect 89
B The hydrogen bond 91
C The mesomeric effect 92
D Hyperconjugation 96
3 Polarizability of charge within molecules 97
A The inductomeric effect 98
B The electromeric effect 98
6 Physical properties of organic compounds 1 100
1 Dipole moments 100
2 Melting points and boiling points 105
3 -Solubility 111
7 Physical properties of organic compounds 2 114
1 Introduction 114
2 Nuclear magnetic resonance spectra 115
3 Infrared spectra 126
4 Electronic absorption spectra 133
5 Molecular refractions 143
Problems 148
8 General principles of organic reaction mechanisms 1 149
1 Introduction 149
2 Some concepts and terms of thermodynamics and kinetics 149
3 Homolytic fission and free radicals 152
9 General principles of organic reaction mechanisms 2 162
1 Heterolysis versus homolysis 162
2 Types of reagents 164
3 Carbonium ions 166
4 Carbanions 170
5 Racemization, epimerization and cis-trans isomerization 176
10 General principles of organic reaction mechanisms 3 179
1 Types of reactions 179
2 Addition reactions 179
A Electrophilic addition 180
B Nucleophilic addition 182
C Free radical addition 183
3 Elimination reactions 185
4 Substitution reactions 194
A Nucleophilic substitution at saturated carbon 194
B Nucleophilic substitution at unsaturated carbon and in aromatic molecules 200
C Electrophilic substitution in aromatic molecules 204
D Free radical substitutions i 215
Problems 217
vii
11 Mass spectra
1 Origin of mass spectra
2 General features of mass spectra
3 Fragmentation patterns
12 Hydrocarbons
1 Summary of basic structural features
2 Saturated hydrocarbons: the C—C and C—H bonds
A Alkanes
B Cycloalkanes
3 Unsaturated hydrocarbons: the C=C and C=C bonds
A Alkenes and cycloalkenes
(i) Electrophilic addition reactions
(ii) Free radical reactions
(iii) Reduction and oxidation reactions
B Conjugated dienes
C Alkynes
(i) Addition reactions
(ii) Reduction and oxidation reactions
(iii) Substitution reactions
4 Aromatic hydrocarbons
A The concept of aromatic character
B Orientation of substituents
C Electrophilic substitution reactions
D Miscellaneous reactions of benzene
5 Alkylbenzenes and alkenylbenzenes
6 Summary of important methods of synthesis
Problems
13 Compounds containing halogens
1 Summary of basic structural features
2 Monohalogen compounds: the C—X bond
A Nucleophilic substitution reactions
B Elimination reactions
C Reactions involving metals
(i) Metal as catalyst
(ii) Metal as electron donor
(iii) Formation of organometallic compounds
D Electrophilic addition and substitution reactions
3 Di- and polyhalogen compounds
4 Fluorine compounds
5 Summary of important methods of synthesis
Problems
14 Ethers and hydroxy compounds
1 Summary of basic structural features
2 Ethers and monohydroxy compounds: the C—O bond
A Nucleophilic substitution reactions
viii Contents
B Nucleophilic addition reactions
C Elimination reactions
D Electrophilic addition and substitution reactions
3 Monohydroxy compounds: the O—H bond
A Reactions involving only the O—H bond
B Oxidation and reduction reactions
4 Dihydroxy compounds
5 Polyhydroxy compounds
6 Summary of important methods of synthesis
Problems
15 Carbonyl compounds 1 349
1 Summary of basic structural features 349
2 Reactions of carbonyl compounds: the C=0 bond 350
• A Nucleophilic addition reactions 350
B Reactions of the hydrocarbon moiety 359
C Oxidation and reduction reactions 365
3 Summary of important methods of synthesis 369
Problems 370
16 Carbonyl compounds 2 373
1 Summary of basic structural features 373
2 Carboxylic acids and their derivatives 375
A Nucleophilic substitution reactions 376
B Reduction of acids and acid derivatives 383
C Reactions of the hydrocarbon moiety 385
D Miscellaneous reactions of acids and acid derivatives 388
(/) Acids 388
(ii) Acid chlorides 394
(iii) Acid amides 394
(iv) Acid salts 396
3 Ketene 397
4 a,^-Unsaturated carbonyl compounds 399
A Electrophilic addition reactions 400
B Nucleophilic addition reactions 401
C Oxidation and reduction 405
5 Summary of important methods of synthesis 406
Problems 407
17 Compounds containing sulphur 411
1 Discussion of basic structural features 411
2 Thioethers and thiols: the C—S bond 415
3 Thiols: the S—H bond 419
4 Thiocarbonyl compounds: the C=S bond 421
5 Sulphonic acids and their derivatives 423
Problems 427
18 Compounds containing nitrogen 1 429
1 Summary of basic structural features 429
Contents ix
2 Amines: the N—H bond 431
3 Amines: the C—N bond 436
A C—N bond rupture by nucleophiles or electrophiles 437
B Electrophilic substitution reactions 441
C Oxidation of amines 443
4 Quaternary compounds and jV-oxides 444
5 Diazonium, azo and hydrazo compounds 446
A Reactions of diazonium compounds: the C=N bond is ruptured 446
B Reactions of diazonium compounds: the C=N bond remains intact 449
C Azo compounds 451
D Hydrazo compounds 452
6 Compounds containing phosphorus: the C—P bond 453
7 Summary of important methods of synthesis 455
Problems 456
19 Compounds containing nitrogen 2 459
1 Summary of basic structural features 459
2 Nitriles: the C=N bond 462
A Nucleophilic addition reactions 463
B Miscellaneous reactions of nitriles * 465
+ —
3 Isonitriles: the N=C bond 466
4 Imines and oximes: the C=N bond 468
5 C-nitroso compounds: the N=0 bond 471
6 Nitro compounds 472
A Nitroalkanes 473
B a,^-Unsaturated nitro compounds 475
C Aromatic nitro compounds 476
7 Summary of important methods of synthesis 477
Problems 478
20 Heterocyclic compounds 480
1 Discussion of basic structural features 480
2 Pyridine 487
A Electrophilic reactions at the nitrogen atom 487
B Electrophilic substitution reactions 488
C Nucleophilic substitution reactions 489
D Reduction and oxidation 491
E Reactions of substituents • 492
3 Pyrrole, furan and thiophene 493
A Electrophilic substitution reactions 494
B Reduction and oxidation 495
C Miscellaneous reactions 496
4 Summary of important methods of synthesis 497
Problems 497
21 Intramolecular group interactions
1 Acid-base interactions
2 Tautomeric interactions
1^5
x Contents
3 Neighbouring group participation: intramolecular catalysis 510
4 Transannular interactions 518
5 Syntheses of ring compounds 519
Problems 525
Miscellaneous syntheses 528
Important sources of further information 530
Index 533
|
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| author | Reid, K. F. |
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| discipline | Chemie / Pharmazie |
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| illustrated | Not Illustrated |
| indexdate | 2024-07-09T16:57:38Z |
| institution | BVB |
| language | English |
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| physical | XIII,556 S.m.Abb.u.Tab. |
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| publishDate | 1968 |
| publishDateSearch | 1968 |
| publishDateSort | 1968 |
| publisher | Longmans |
| record_format | marc |
| spelling | Reid, K. F. Verfasser aut Properties and reactions of bonds in organic molecules London Longmans 1968 XIII,556 S.m.Abb.u.Tab. txt rdacontent n rdamedia nc rdacarrier Chemical bonds Chemistry, Organic Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Chemische Bindung (DE-588)4009843-6 gnd rswk-swf Theoretische organische Chemie (DE-588)4185101-8 gnd rswk-swf Theoretische organische Chemie (DE-588)4185101-8 s DE-604 Chemische Bindung (DE-588)4009843-6 s Organische Verbindungen (DE-588)4043816-8 s HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=004612489&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Reid, K. F. Properties and reactions of bonds in organic molecules Chemical bonds Chemistry, Organic Organische Verbindungen (DE-588)4043816-8 gnd Chemische Bindung (DE-588)4009843-6 gnd Theoretische organische Chemie (DE-588)4185101-8 gnd |
| subject_GND | (DE-588)4043816-8 (DE-588)4009843-6 (DE-588)4185101-8 |
| title | Properties and reactions of bonds in organic molecules |
| title_auth | Properties and reactions of bonds in organic molecules |
| title_exact_search | Properties and reactions of bonds in organic molecules |
| title_full | Properties and reactions of bonds in organic molecules |
| title_fullStr | Properties and reactions of bonds in organic molecules |
| title_full_unstemmed | Properties and reactions of bonds in organic molecules |
| title_short | Properties and reactions of bonds in organic molecules |
| title_sort | properties and reactions of bonds in organic molecules |
| topic | Chemical bonds Chemistry, Organic Organische Verbindungen (DE-588)4043816-8 gnd Chemische Bindung (DE-588)4009843-6 gnd Theoretische organische Chemie (DE-588)4185101-8 gnd |
| topic_facet | Chemical bonds Chemistry, Organic Organische Verbindungen Chemische Bindung Theoretische organische Chemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=004612489&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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