Beruflich Dokumente
Kultur Dokumente
Preface
xxv
INTRODUCTION
CHAPTER 1
CHEMICAL BONDING
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9
1.10
27
1.11
1.12
1.13
1.14
1.15
1.16
1.17
1.18
1.19
1.20
SUMMARY
43
PROBLEMS
47
CHAPTER 2
ALKANES
53
2.1
2.2
2.3
2.4
2.5
Classes of Hydrocarbons 53
Reactive Sites in Hydrocarbons 54
The Key Functional Groups 55
Introduction to Alkanes: Methane, Ethane, and Propane
Isomeric Alkanes: The Butanes 57
56
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xii
CONTENTS
2.6
2.7
2.8
2.9
Higher n-Alkanes 59
The C5H12 Isomers 59
IUPAC Nomenclature of Unbranched Alkanes 61
Applying the IUPAC Rules: The Names of the C6H14 Isomers
62
Alkyl Groups 65
IUPAC Names of Highly Branched Alkanes 66
Cycloalkane Nomenclature 68
Sources of Alkanes and Cycloalkanes 69
Physical Properties of Alkanes and Cycloalkanes 71
Chemical Properties. Combustion of Alkanes 74
Thermochemistry 77
2.16
2.17
78
80
83
CHAPTER 3
CONFORMATIONS OF ALKANES AND CYCLOALKANES
3.1
3.2
89
3.3
3.4
3.5
3.6
3.7
3.8
3.16
SUMMARY
PROBLEMS
Forward
110
117
120
CHAPTER 4
ALCOHOLS AND ALKYL HALIDES
Back
106
3.9
3.10
3.11
3.12
3.13
3.14
3.15
4.1
4.2
4.3
4.4
4.5
4.6
4.7
4.8
4.9
4.10
96
126
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4.11
4.12
4.13
4.14
4.15
4.16
4.17
4.18
xiii
4.19
4.20
SUMMARY
155
156
159
PROBLEMS
163
CHAPTER 5
STRUCTURE AND PREPARATION OF ALKENES: ELIMINATION
REACTIONS
167
5.1
5.2
5.3
5.4
5.5
5.6
5.7
5.8
5.9
5.10
5.11
5.12
5.13
5.14
5.15
5.16
5.17
5.18
168
198
202
CHAPTER 6
REACTIONS OF ALKENES: ADDITION REACTIONS
6.1
6.2
6.3
6.4
6.5
6.6
6.7
6.8
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208
214
217
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219
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xiv
CONTENTS
6.9
6.10
6.11
6.12
6.13
6.14
6.15
6.16
6.17
6.18
6.19
6.20
6.21
234
SUMMARY
PROBLEMS
249
252
CHAPTER 7
STEREOCHEMISTRY
7.1
7.2
7.3
7.4
7.5
7.6
7.7
7.8
7.9
7.10
7.11
259
273
281
7.12
7.13
7.14
7.15
7.16
7.17
SUMMARY
PROBLEMS
290
293
CHAPTER 8
NUCLEOPHILIC SUBSTITUTION
8.1
8.2
8.3
8.4
8.5
8.6
8.7
302
302
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8.8
8.9
8.10
8.11
8.12
8.13
8.14
8.15
8.16
xv
330
332
CHAPTER 9
ALKYNES
339
9.1
9.2
9.3
9.4
9.5
9.6
341
344
9.7
9.8
9.9
9.10
9.11
9.12
9.13
9.14
9.15
SUMMARY
PROBLEMS
357
358
CHAPTER 10
CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS
10.1
10.2
10.3
10.4
10.5
10.6
10.7
10.8
10.9
10.10
10.11
10.12
365
379
383
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390
393
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xvi
CONTENTS
CHAPTER 11
ARENES AND AROMATICITY
11.1
11.2
398
Benzene 399
Kekul and the Structure of Benzene
399
401
11.9
11.10
11.11
11.12
11.13
11.14
11.15
11.16
11.17
11.18
11.19
11.20
11.21
11.22
410
11.23 SUMMARY
PROBLEMS
432
433
437
CHAPTER 12
REACTIONS OF ARENES: ELECTROPHILIC AROMATIC
SUBSTITUTION
443
12.1
12.2
12.3
12.4
12.5
12.6
12.7
12.8
12.9
12.10
12.11
12.12
12.13
12.14
12.15
12.16
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12.17 Substitution in Naphthalene 474
12.18 Substitution in Heterocyclic Aromatic Compounds
12.19 SUMMARY
PROBLEMS
475
477
480
CHAPTER 13
SPECTROSCOPY
13.1
13.2
13.3
13.4
13.5
13.6
13.7
13.8
13.9
13.10
13.11
13.12
13.13
13.14
13.15
13.16
13.17
13.18
xvii
487
517
522
530
533
536
CHAPTER 14
ORGANOMETALLIC COMPOUNDS
14.1
14.2
14.3
14.4
14.5
14.6
14.7
14.8
14.9
14.10
14.11
14.12
14.13
14.14
14.15
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546
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xviii
CONTENTS
An Organometallic Compound That Occurs Naturally:
Coenzyme B12 568
14.16 SUMMARY
PROBLEMS
570
573
CHAPTER 15
ALCOHOLS, DIOLS, AND THIOLS
15.1
15.2
15.3
15.4
15.5
15.6
15.7
15.8
15.9
15.10
579
15.11
15.12
15.13
15.14
15.15
15.16 SUMMARY
PROBLEMS
607
611
CHAPTER 16
ETHERS, EPOXIDES, AND SULFIDES
16.1
16.2
16.3
16.4
PROBLEMS
Forward
624
16.19 SUMMARY
Back
619
16.5
16.6
16.7
16.8
16.9
16.10
16.11
16.12
16.13
16.14
16.15
16.16
16.17
16.18
598
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643
647
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xix
CHAPTER 17
ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL
GROUP
654
17.1
17.2
17.3
17.4
17.5
17.6
Nomenclature 654
Structure and Bonding: The Carbonyl Group 657
Physical Properties 658
Sources of Aldehydes and Ketones 659
Reactions of Aldehydes and Ketones: A Review and a Preview 661
Principles of Nucleophilic Addition: Hydration of Aldehydes and
Ketones 663
17.7 Cyanohydrin Formation 667
17.8 Acetal Formation 668
17.9 Acetals as Protecting Groups 671
17.10 Reaction with Primary Amines: Imines 672
17.11 Reaction with Secondary Amines: Enamines 674
Imines in Biological Chemistry 675
17.12
17.13
17.14
17.15
17.16
17.17
17.18 SUMMARY
PROBLEMS
688
691
CHAPTER 18
ENOLS AND ENOLATES
18.1
18.2
18.3
18.4
18.5
18.6
18.7
701
703
713
18.8
18.9
18.10
18.11
18.12
18.13
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726
726
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xx
CONTENTS
CHAPTER 19
CARBOXYLIC ACIDS
19.1
19.2
19.3
19.4
19.5
736
19.6
19.7
19.8
19.9
19.10
19.11
19.12
19.13
19.14
19.15
19.16
19.17
19.18
743
19.19 SUMMARY
PROBLEMS
765
768
CHAPTER 20
CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL
SUBSTITUTION
774
20.1
20.2
20.3
20.4
20.5
20.6
20.7
20.8
20.9
20.10
20.11
20.12
20.13
20.14
20.15
20.16
20.17
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809
816
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20.21 Spectroscopic Analysis of Carboxylic Acid Derivatives
20.22 SUMMARY
PROBLEMS
817
819
822
CHAPTER 21
ESTER ENOLATES
21.1
21.2
21.3
21.4
21.5
21.6
21.7
21.8
21.9
21.10
xxi
831
21.11 SUMMARY
PROBLEMS
850
853
CHAPTER 22
AMINES
858
22.1
22.2
22.3
22.4
22.5
22.6
22.7
22.8
22.9
22.10
22.11
22.12
22.13
22.14
22.15
22.16
22.17
22.18
22.19
869
896
CHAPTER 23
ARYL HALIDES
23.1
23.2
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897
900
907
917
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xxii
CONTENTS
23.3
23.4
23.5
23.6
23.7
23.8
23.9
23.10 SUMMARY
PROBLEMS
932
934
CHAPTER 24
PHENOLS
939
24.1
24.2
24.3
24.4
24.5
24.6
24.7
24.8
24.9
24.10
24.11
Nomenclature 939
Structure and Bonding 940
Physical Properties 941
Acidity of Phenols 942
Substituent Effects on the Acidity of Phenols 944
Sources of Phenols 946
Naturally Occurring Phenols 946
Reactions of Phenols: Electrophilic Aromatic Substitution 948
Acylation of Phenols 949
Carboxylation of Phenols: Aspirin and the KolbeSchmitt Reaction
Preparation of Aryl Ethers 954
Agent Orange and Dioxin
24.12
24.13
24.14
24.15
PROBLEMS
962
965
CHAPTER 25
CARBOHYDRATES
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955
24.16 SUMMARY
25.1
25.2
25.3
25.4
25.5
25.6
25.7
25.8
25.9
25.10
25.11
25.12
25.13
25.14
25.15
25.16
25.17
25.18
952
972
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How Sweet It Is!
xxiii
997
1006
1008
CHAPTER 26
LIPIDS
1015
26.1
26.2
26.3
26.4
26.5
26.6
26.7
26.8
26.9
26.10
26.11
26.12
26.13
26.14
26.15
Vitamin D 1038
Bile Acids 1039
Corticosteroids 1040
Sex Hormones 1040
Anabolic Steroids
26.16 Carotenoids
26.17 SUMMARY
PROBLEMS
1041
1042
1042
1045
CHAPTER 27
AMINO ACIDS, PEPTIDES, AND PROTEINS. NUCLEIC ACIDS
27.1
27.2
27.3
Electrophoresis
27.4
27.5
27.6
27.7
27.8
27.9
27.10
27.11
27.12
27.13
27.14
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1051
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1074
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xxiv
CONTENTS
27.15
27.16
27.17
27.18
27.19
27.20
27.21
27.22
27.23
27.24
27.25
27.26
27.27
27.28
1098
1103
1106
APPENDIX 1
PHYSICAL PROPERTIES
A-1
APPENDIX 2
APPENDIX 3
A-9
GLOSSARY G-1
CREDITS C-1
INDEX I-1
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