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Organic Chemistry, 4th Edition provides a comprehensive, yet accessible treatment of all the essential organic chemistry concepts covered in a two-semester course. Presented with a skills-based approach that bridges the gap between organic chemistry theory and real-world practice, the book places special emphasis on developing their problem-solving skills through applied exercises and activities. It incorporates Klein's acclaimed SkillBuilder program which contains a solved problem that demonstrates a skill and several practice problems of varying difficulty levels?including conceptual and cumulative problems that challenge students to apply the skill in a slightly different environment. An up-to-date collection of literature-based problems exposes students to the dynamic and evolving nature of organic chemistry and its active role in addressing global challenges. The text is also enriched with numerous hands-on activities and real-world examples that help students understand both the "why" and the "how" behind organic chemistry.
Organic Chemistry, 4th Edition provides a comprehensive, yet accessible treatment of all the essential organic chemistry concepts covered in a two-semester course. Presented with a skills-based approach that bridges the gap between organic chemistry theory and real-world practice, the book places special emphasis on developing their problem-solving skills through applied exercises and activities. It incorporates Klein's acclaimed SkillBuilder program which contains a solved problem that demonstrates a skill and several practice problems of varying difficulty levels?including conceptual and cumulative problems that challenge students to apply the skill in a slightly different environment. An up-to-date collection of literature-based problems exposes students to the dynamic and evolving nature of organic chemistry and its active role in addressing global challenges. The text is also enriched with numerous hands-on activities and real-world examples that help students understand both the "why" and the "how" behind organic chemistry.
Inhaltsverzeichnis
1 A Review of General Chemistry: Electrons, Bonds, and Molecular Properties 1
1.1 Introduction to Organic Chemistry 2
1.2 The Structural Theory of Matter 3
1.3 Electrons, Bonds, and Lewis Structures 4
1.4 Identifying Formal Charges 7
1.5 Induction and Polar Covalent Bonds 8
1.6 Reading Bond- Line Structures 11
1.7 Atomic Orbitals 14
1.8 Valence Bond Theory 17
1.9 Molecular Orbital Theory 18
1.10 Hybridized Atomic Orbitals 20
1.11 Predicting Molecular Geometry: VSEPR Theory 26
1.12 Dipole Moments and Molecular Polarity 30
1.13 Intermolecular Forces and Physical Properties 33
WorldLinks Biomimicry and Gecko Feet 37
BioLinks Drug- Receptor Interactions 38
1.14 Solubility 39
BioLinks Propofol: The Importance of Drug Solubility 40
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
2 Molecular Representations 49
2.1 Molecular Representations 50
2.2 Bond- Line Structures 52
2.3 Identifying Functional Groups 54
BioLinks Marine Natural Products 55
2.4 Carbon Atoms with Formal Charges 57
2.5 Identifying Lone Pairs 57
2.6 Three- Dimensional Bond- Line Structures 60
BioLinks The Opioids 61
2.7 Introduction to Resonance 62
2.8 Curved Arrows 64
2.9 Formal Charges in Resonance Structures 66
2.10 Drawing Resonance Structures via Pattern Recognition 68
2.11 Assessing the Relative Importance of Resonance Structures 73
2.12 The Resonance Hybrid 77
2.13 Delocalized and Localized Lone Pairs 79
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
3 Acids and Bases 91
3.1 Introduction to Brønsted- Lowry Acids and Bases 92
3.2 Flow of Electron Density: Curved- Arrow Notation 92
BioLinks Antacids and Heartburn 94
3.3 Brønsted- Lowry Acidity: Quantitative Perspective 95
BioLinks Drug Distribution and pK a 101
3.4 Brønsted- Lowry Acidity: Qualitative Perspective 102
3.5 Brønsted- Lowry Acidity: Assessing the Relative Acidity of Cationic Acids 113
3.6 Position of Equilibrium and Choice of Reagents 118
3.7 Leveling Effect 121
3.8 Solvating Effects 122
3.9 Counterions 123
WorldLinks Baking Soda versus Baking Powder 123
3.10 Lewis Acids and Bases 124
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
4 Alkanes and Cycloalkanes 137
4.1 Introduction to Alkanes 138
4.2 Nomenclature of Alkanes 138
WorldLinks Pheromones: Chemical Messengers 142
BioLinks Naming Drugs 150
4.3 Constitutional Isomers of Alkanes 151
4.4 Relative Stability of Isomeric Alkanes 152
4.5 Sources and Uses of Alkanes 153
WorldLinks An Introduction to Polymers 155
4.6 Drawing Newman Projections 155
4.7 Conformational Analysis of Ethane and Propane 157
4.8 Conformational Analysis of Butane 159
BioLinks Drugs and Their Conformations 163
4.9 Cycloalkanes 163
BioLinks Cyclopropane as an Inhalation Anesthetic 165
4.10 Conformations of Cyclohexane 166
4.11 Drawing Chair Conformations 167
4.12 Monosubstituted Cyclohexane 169
4.13 Disubstituted Cyclohexane 171
4.14 cis-trans Stereoisomerism 175
4.15 Polycyclic Systems 176
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
5 Stereoisomerism 187
5.1 Overview of Isomerism 188
5.2 Introduction to Stereoisomerism 189
WorldLinks The Sense of Smell 194
5.3 Designating Configuration Using the Cahn-Ingold-Prelog System 194
BioLinks Chiral Drugs 199
5.4 Optical Activity 200
5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers 206
5.6 Symmetry and Chirality 209
5.7 Fischer Projections 213
5.8 Conformationally Mobile Systems 215
5.9 Chirality without a Chiral Center 216
5.10 Resolution of Racemic Mixtures 217
5.11 Asymmetric Synthesis: Stereoselective and Stereospecific Reactions 219
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
6 Chemical Reactivity and Mechanisms 229
6.1 Enthalpy 230
6.2 Entropy 233
6.3 Gibbs Free Energy 235
WorldLinks Explosives 236
WorldLinks Do Living Organisms Violate the Second Law of Thermodynamics? 238
6.4 Equilibria 238
6.5 Kinetics 240
BioLinks Nitroglycerin: An Explosive with Medicinal Properties 243
WorldLinks Beer Making 244
6.6 Energy Diagrams 245
6.7 Nucleophiles and Electrophiles 248
6.8 Mechanisms and Arrow Pushing 252
6.9 Combining the Patterns of Arrow Pushing 257
6.10 Drawing Curved Arrows 259
6.11 Carbocation Rearrangements 262
6.12 Reversible and Irreversible Reaction Arrows 264
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
7 Substitution Reactions 277
7.1 Introduction to Substitution Reactions 278
7.2 Alkyl Halides 279
7.3 Possible Mechanisms for Substitution Reactions 283
7.4 The S N 2 Mechanism 285
BioLinks Pharmacology and Drug Design 291
7.5 Nucleophilic Strength in S N 2 Reactions 293
BioLinks S N 2 Reactions in Biological Systems--Methylation 293
7.6 The S N 1 Mechanism 295
7.7 Solvent Effects in Substitution Reactions 301
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems * Integrated Problems Challenge Problems
8 Alkenes: Structure and Preparation via Elimination Reactions 313
8.1 Introduction to Elimination Reactions 314
8.2 Stereoisomerism in Alkenes 314
BioLinks Phototherapy Treatment for Neonatal Jaundice 317
8.3 Stability of Alkenes and Cycloalkenes 319
8.4 Possible Mechanisms for Elimination Reactions 321
8.5 The E2 Mechanism 323
8.6 Regiochemical and Stereochemical Outcomes for E2 Reactions 325
8.7 The E1 Mechanism 335
8.8 Predicting Products: Substitution vs. Elimination 342
8.9 Substitution and Elimination Reactions with Other Substrates 348
8.10 Synthesis Strategies - Substitution and Elimination 352
BioLinks Radiolabeled Compounds in Diagnostic Medicine 356
SpecialTopic Kinetic Isotope Effects 361
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
9 Addition Reactions of Alkenes 371
9.1 Introduction to Addition Reactions 372
9.2 Alkenes in Nature and in Industry 373
WorldLinks Pheromones to Control Insect Populations 373
9.3 Nomenclature of Alkenes 374
9.4 Addition vs. Elimination: A Thermodynamic Perspective 376
9.5 Hydrohalogenation 377
WorldLinks Cationic Polymerization and Polystyrene 384
9.6 Acid-Catalyzed Hydration 385
9.7 Oxymercuration-Demercuration 389
9.8 Hydroboration-Oxidation 390
9.9 Catalytic Hydrogenation 396
WorldLinks Partially Hydrogenated Fats and Oils 401
9.10 Halogenation and Halohydrin Formation 402
9.11 Anti Dihydroxylation 406
9.12 Syn Dihydroxylation 409
9.13 Oxidative Cleavage 411
9.14 Predicting the Products of an Addition Reaction 413
9.15 Synthesis Strategies 415
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
10 Alkynes 431
10.1 Introduction to Alkynes 432
BioLinks The Role of Molecular Rigidity 434
WorldLinks Conducting Organic Polymers 435
10.2 Nomenclature of Alkynes 435
10.3 Acidity of Acetylene and Terminal Alkynes 437
10.4 Preparation of Alkynes 440
10.5 Reduction of Alkynes 442
10.6 Hydrohalogenation of Alkynes 445
10.7 Hydration of Alkynes 447
10.8 Halogenation of Alkynes 453
10.9 Ozonolysis of Alkynes 453
10.10 Alkylation of Terminal Alkynes 454
10.11 Synthesis Strategies 456
Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
11 Radical Reactions 467
11.1 Radicals 468
11.2 Common Patterns in Radical Mechanisms 473
11.3 Chlorination of Methane 476
11.4 Thermodynamic Considerations for Halogenation Reactions 480
11.5 Selectivity of Halogenation 482
11.6 Stereochemistry of Halogenation 485
11.7 Allylic Bromination 487
11.8 Atmospheric Chemistry and the Ozone Layer 490
WorldLinks Fighting Fires with Chemicals 492
11.9 Autooxidation and Antioxidants 493
BioLinks Why Is an Overdose of Acetaminophen Fatal? 495
11.10 Radical Addition of HBr: Anti-Markovnikov Addition 496
11.11 Radical Polymerization 500
11.12 Radical Processes in the Petrochemical Industry 502
11.13 Halogenation as a Synthetic Technique 502
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
12 Systematic Approach to Synthesis 511
12.1 One-Step Syntheses 512
12.2 Functional Group Transformations 513
12.3 Reactions That Change the Carbon Skeleton 517
BioLinks Vitamins 519
12.4 How to Approach a Synthesis Problem 520
BioLinks The Total Synthesis of Vitamin B 12 524
12.5 Multi- Step Synthesis and Retrosynthetic Analysis 526
WorldLinks Retrosynthetic Analysis 531
12.6 Green Chemistry 531
12.7 Practical Tips for Increasing Proficiency 532
BioLinks Total Synthesis of Taxol 533
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems Review of Reactions * 13 Alcohols and Phenols 541
13.1 Structure and Properties of Alcohols 542
BioLinks Chain Length as a Factor in Drug Design 546
13.2 Acidity of Alcohols and Phenols 547
13.3 Preparation of Alcohols via Substitution or Addition 550
13.4 Preparation of Alcohols via Reduction 551
13.5 Preparation of Diols 558
WorldLinks Antifreeze 559
13.6 Preparation of Alcohols via Grignard Reagents 559
13.7 Protection of Alcohols 564
13.8 Preparation of Phenols 565
13.9 Reactions of Alcohols: Substitution and Elimination 566
BioLinks Drug Metabolism 569
13.10 Reactions of Alcohols: Oxidation 571
13.11 Biological Redox Reactions 575
BioLinks Biological Oxidation of Methanol and Ethanol 577
13.12 Oxidation of Phenol 577
13.13 Synthesis Strategies 579
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder...
1.1 Introduction to Organic Chemistry 2
1.2 The Structural Theory of Matter 3
1.3 Electrons, Bonds, and Lewis Structures 4
1.4 Identifying Formal Charges 7
1.5 Induction and Polar Covalent Bonds 8
1.6 Reading Bond- Line Structures 11
1.7 Atomic Orbitals 14
1.8 Valence Bond Theory 17
1.9 Molecular Orbital Theory 18
1.10 Hybridized Atomic Orbitals 20
1.11 Predicting Molecular Geometry: VSEPR Theory 26
1.12 Dipole Moments and Molecular Polarity 30
1.13 Intermolecular Forces and Physical Properties 33
WorldLinks Biomimicry and Gecko Feet 37
BioLinks Drug- Receptor Interactions 38
1.14 Solubility 39
BioLinks Propofol: The Importance of Drug Solubility 40
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
2 Molecular Representations 49
2.1 Molecular Representations 50
2.2 Bond- Line Structures 52
2.3 Identifying Functional Groups 54
BioLinks Marine Natural Products 55
2.4 Carbon Atoms with Formal Charges 57
2.5 Identifying Lone Pairs 57
2.6 Three- Dimensional Bond- Line Structures 60
BioLinks The Opioids 61
2.7 Introduction to Resonance 62
2.8 Curved Arrows 64
2.9 Formal Charges in Resonance Structures 66
2.10 Drawing Resonance Structures via Pattern Recognition 68
2.11 Assessing the Relative Importance of Resonance Structures 73
2.12 The Resonance Hybrid 77
2.13 Delocalized and Localized Lone Pairs 79
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
3 Acids and Bases 91
3.1 Introduction to Brønsted- Lowry Acids and Bases 92
3.2 Flow of Electron Density: Curved- Arrow Notation 92
BioLinks Antacids and Heartburn 94
3.3 Brønsted- Lowry Acidity: Quantitative Perspective 95
BioLinks Drug Distribution and pK a 101
3.4 Brønsted- Lowry Acidity: Qualitative Perspective 102
3.5 Brønsted- Lowry Acidity: Assessing the Relative Acidity of Cationic Acids 113
3.6 Position of Equilibrium and Choice of Reagents 118
3.7 Leveling Effect 121
3.8 Solvating Effects 122
3.9 Counterions 123
WorldLinks Baking Soda versus Baking Powder 123
3.10 Lewis Acids and Bases 124
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
4 Alkanes and Cycloalkanes 137
4.1 Introduction to Alkanes 138
4.2 Nomenclature of Alkanes 138
WorldLinks Pheromones: Chemical Messengers 142
BioLinks Naming Drugs 150
4.3 Constitutional Isomers of Alkanes 151
4.4 Relative Stability of Isomeric Alkanes 152
4.5 Sources and Uses of Alkanes 153
WorldLinks An Introduction to Polymers 155
4.6 Drawing Newman Projections 155
4.7 Conformational Analysis of Ethane and Propane 157
4.8 Conformational Analysis of Butane 159
BioLinks Drugs and Their Conformations 163
4.9 Cycloalkanes 163
BioLinks Cyclopropane as an Inhalation Anesthetic 165
4.10 Conformations of Cyclohexane 166
4.11 Drawing Chair Conformations 167
4.12 Monosubstituted Cyclohexane 169
4.13 Disubstituted Cyclohexane 171
4.14 cis-trans Stereoisomerism 175
4.15 Polycyclic Systems 176
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
5 Stereoisomerism 187
5.1 Overview of Isomerism 188
5.2 Introduction to Stereoisomerism 189
WorldLinks The Sense of Smell 194
5.3 Designating Configuration Using the Cahn-Ingold-Prelog System 194
BioLinks Chiral Drugs 199
5.4 Optical Activity 200
5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers 206
5.6 Symmetry and Chirality 209
5.7 Fischer Projections 213
5.8 Conformationally Mobile Systems 215
5.9 Chirality without a Chiral Center 216
5.10 Resolution of Racemic Mixtures 217
5.11 Asymmetric Synthesis: Stereoselective and Stereospecific Reactions 219
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
6 Chemical Reactivity and Mechanisms 229
6.1 Enthalpy 230
6.2 Entropy 233
6.3 Gibbs Free Energy 235
WorldLinks Explosives 236
WorldLinks Do Living Organisms Violate the Second Law of Thermodynamics? 238
6.4 Equilibria 238
6.5 Kinetics 240
BioLinks Nitroglycerin: An Explosive with Medicinal Properties 243
WorldLinks Beer Making 244
6.6 Energy Diagrams 245
6.7 Nucleophiles and Electrophiles 248
6.8 Mechanisms and Arrow Pushing 252
6.9 Combining the Patterns of Arrow Pushing 257
6.10 Drawing Curved Arrows 259
6.11 Carbocation Rearrangements 262
6.12 Reversible and Irreversible Reaction Arrows 264
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
7 Substitution Reactions 277
7.1 Introduction to Substitution Reactions 278
7.2 Alkyl Halides 279
7.3 Possible Mechanisms for Substitution Reactions 283
7.4 The S N 2 Mechanism 285
BioLinks Pharmacology and Drug Design 291
7.5 Nucleophilic Strength in S N 2 Reactions 293
BioLinks S N 2 Reactions in Biological Systems--Methylation 293
7.6 The S N 1 Mechanism 295
7.7 Solvent Effects in Substitution Reactions 301
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems * Integrated Problems Challenge Problems
8 Alkenes: Structure and Preparation via Elimination Reactions 313
8.1 Introduction to Elimination Reactions 314
8.2 Stereoisomerism in Alkenes 314
BioLinks Phototherapy Treatment for Neonatal Jaundice 317
8.3 Stability of Alkenes and Cycloalkenes 319
8.4 Possible Mechanisms for Elimination Reactions 321
8.5 The E2 Mechanism 323
8.6 Regiochemical and Stereochemical Outcomes for E2 Reactions 325
8.7 The E1 Mechanism 335
8.8 Predicting Products: Substitution vs. Elimination 342
8.9 Substitution and Elimination Reactions with Other Substrates 348
8.10 Synthesis Strategies - Substitution and Elimination 352
BioLinks Radiolabeled Compounds in Diagnostic Medicine 356
SpecialTopic Kinetic Isotope Effects 361
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
9 Addition Reactions of Alkenes 371
9.1 Introduction to Addition Reactions 372
9.2 Alkenes in Nature and in Industry 373
WorldLinks Pheromones to Control Insect Populations 373
9.3 Nomenclature of Alkenes 374
9.4 Addition vs. Elimination: A Thermodynamic Perspective 376
9.5 Hydrohalogenation 377
WorldLinks Cationic Polymerization and Polystyrene 384
9.6 Acid-Catalyzed Hydration 385
9.7 Oxymercuration-Demercuration 389
9.8 Hydroboration-Oxidation 390
9.9 Catalytic Hydrogenation 396
WorldLinks Partially Hydrogenated Fats and Oils 401
9.10 Halogenation and Halohydrin Formation 402
9.11 Anti Dihydroxylation 406
9.12 Syn Dihydroxylation 409
9.13 Oxidative Cleavage 411
9.14 Predicting the Products of an Addition Reaction 413
9.15 Synthesis Strategies 415
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
10 Alkynes 431
10.1 Introduction to Alkynes 432
BioLinks The Role of Molecular Rigidity 434
WorldLinks Conducting Organic Polymers 435
10.2 Nomenclature of Alkynes 435
10.3 Acidity of Acetylene and Terminal Alkynes 437
10.4 Preparation of Alkynes 440
10.5 Reduction of Alkynes 442
10.6 Hydrohalogenation of Alkynes 445
10.7 Hydration of Alkynes 447
10.8 Halogenation of Alkynes 453
10.9 Ozonolysis of Alkynes 453
10.10 Alkylation of Terminal Alkynes 454
10.11 Synthesis Strategies 456
Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
11 Radical Reactions 467
11.1 Radicals 468
11.2 Common Patterns in Radical Mechanisms 473
11.3 Chlorination of Methane 476
11.4 Thermodynamic Considerations for Halogenation Reactions 480
11.5 Selectivity of Halogenation 482
11.6 Stereochemistry of Halogenation 485
11.7 Allylic Bromination 487
11.8 Atmospheric Chemistry and the Ozone Layer 490
WorldLinks Fighting Fires with Chemicals 492
11.9 Autooxidation and Antioxidants 493
BioLinks Why Is an Overdose of Acetaminophen Fatal? 495
11.10 Radical Addition of HBr: Anti-Markovnikov Addition 496
11.11 Radical Polymerization 500
11.12 Radical Processes in the Petrochemical Industry 502
11.13 Halogenation as a Synthetic Technique 502
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
12 Systematic Approach to Synthesis 511
12.1 One-Step Syntheses 512
12.2 Functional Group Transformations 513
12.3 Reactions That Change the Carbon Skeleton 517
BioLinks Vitamins 519
12.4 How to Approach a Synthesis Problem 520
BioLinks The Total Synthesis of Vitamin B 12 524
12.5 Multi- Step Synthesis and Retrosynthetic Analysis 526
WorldLinks Retrosynthetic Analysis 531
12.6 Green Chemistry 531
12.7 Practical Tips for Increasing Proficiency 532
BioLinks Total Synthesis of Taxol 533
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems Review of Reactions * 13 Alcohols and Phenols 541
13.1 Structure and Properties of Alcohols 542
BioLinks Chain Length as a Factor in Drug Design 546
13.2 Acidity of Alcohols and Phenols 547
13.3 Preparation of Alcohols via Substitution or Addition 550
13.4 Preparation of Alcohols via Reduction 551
13.5 Preparation of Diols 558
WorldLinks Antifreeze 559
13.6 Preparation of Alcohols via Grignard Reagents 559
13.7 Protection of Alcohols 564
13.8 Preparation of Phenols 565
13.9 Reactions of Alcohols: Substitution and Elimination 566
BioLinks Drug Metabolism 569
13.10 Reactions of Alcohols: Oxidation 571
13.11 Biological Redox Reactions 575
BioLinks Biological Oxidation of Methanol and Ethanol 577
13.12 Oxidation of Phenol 577
13.13 Synthesis Strategies 579
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder...
Details
| Erscheinungsjahr: | 2022 |
|---|---|
| Fachbereich: | Organische Chemie |
| Genre: | Chemie |
| Rubrik: | Naturwissenschaften & Technik |
| Medium: | Taschenbuch |
| Seiten: | 1296 |
| Inhalt: | 1392 S. |
| ISBN-13: | 9781119820833 |
| ISBN-10: | 1119820839 |
| Sprache: | Englisch |
| Herstellernummer: | 1W119820830 |
| Einband: | Kartoniert / Broschiert |
| Autor: | Klein, David R. |
| Auflage: | 4. Auflage |
| Hersteller: | Wiley John + Sons |
| Maße: | 276 x 216 x 52 mm |
| Von/Mit: | David R. Klein |
| Erscheinungsdatum: | 22.09.2022 |
| Gewicht: | 2,939 kg |
Inhaltsverzeichnis
1 A Review of General Chemistry: Electrons, Bonds, and Molecular Properties 1
1.1 Introduction to Organic Chemistry 2
1.2 The Structural Theory of Matter 3
1.3 Electrons, Bonds, and Lewis Structures 4
1.4 Identifying Formal Charges 7
1.5 Induction and Polar Covalent Bonds 8
1.6 Reading Bond- Line Structures 11
1.7 Atomic Orbitals 14
1.8 Valence Bond Theory 17
1.9 Molecular Orbital Theory 18
1.10 Hybridized Atomic Orbitals 20
1.11 Predicting Molecular Geometry: VSEPR Theory 26
1.12 Dipole Moments and Molecular Polarity 30
1.13 Intermolecular Forces and Physical Properties 33
WorldLinks Biomimicry and Gecko Feet 37
BioLinks Drug- Receptor Interactions 38
1.14 Solubility 39
BioLinks Propofol: The Importance of Drug Solubility 40
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
2 Molecular Representations 49
2.1 Molecular Representations 50
2.2 Bond- Line Structures 52
2.3 Identifying Functional Groups 54
BioLinks Marine Natural Products 55
2.4 Carbon Atoms with Formal Charges 57
2.5 Identifying Lone Pairs 57
2.6 Three- Dimensional Bond- Line Structures 60
BioLinks The Opioids 61
2.7 Introduction to Resonance 62
2.8 Curved Arrows 64
2.9 Formal Charges in Resonance Structures 66
2.10 Drawing Resonance Structures via Pattern Recognition 68
2.11 Assessing the Relative Importance of Resonance Structures 73
2.12 The Resonance Hybrid 77
2.13 Delocalized and Localized Lone Pairs 79
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
3 Acids and Bases 91
3.1 Introduction to Brønsted- Lowry Acids and Bases 92
3.2 Flow of Electron Density: Curved- Arrow Notation 92
BioLinks Antacids and Heartburn 94
3.3 Brønsted- Lowry Acidity: Quantitative Perspective 95
BioLinks Drug Distribution and pK a 101
3.4 Brønsted- Lowry Acidity: Qualitative Perspective 102
3.5 Brønsted- Lowry Acidity: Assessing the Relative Acidity of Cationic Acids 113
3.6 Position of Equilibrium and Choice of Reagents 118
3.7 Leveling Effect 121
3.8 Solvating Effects 122
3.9 Counterions 123
WorldLinks Baking Soda versus Baking Powder 123
3.10 Lewis Acids and Bases 124
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
4 Alkanes and Cycloalkanes 137
4.1 Introduction to Alkanes 138
4.2 Nomenclature of Alkanes 138
WorldLinks Pheromones: Chemical Messengers 142
BioLinks Naming Drugs 150
4.3 Constitutional Isomers of Alkanes 151
4.4 Relative Stability of Isomeric Alkanes 152
4.5 Sources and Uses of Alkanes 153
WorldLinks An Introduction to Polymers 155
4.6 Drawing Newman Projections 155
4.7 Conformational Analysis of Ethane and Propane 157
4.8 Conformational Analysis of Butane 159
BioLinks Drugs and Their Conformations 163
4.9 Cycloalkanes 163
BioLinks Cyclopropane as an Inhalation Anesthetic 165
4.10 Conformations of Cyclohexane 166
4.11 Drawing Chair Conformations 167
4.12 Monosubstituted Cyclohexane 169
4.13 Disubstituted Cyclohexane 171
4.14 cis-trans Stereoisomerism 175
4.15 Polycyclic Systems 176
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
5 Stereoisomerism 187
5.1 Overview of Isomerism 188
5.2 Introduction to Stereoisomerism 189
WorldLinks The Sense of Smell 194
5.3 Designating Configuration Using the Cahn-Ingold-Prelog System 194
BioLinks Chiral Drugs 199
5.4 Optical Activity 200
5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers 206
5.6 Symmetry and Chirality 209
5.7 Fischer Projections 213
5.8 Conformationally Mobile Systems 215
5.9 Chirality without a Chiral Center 216
5.10 Resolution of Racemic Mixtures 217
5.11 Asymmetric Synthesis: Stereoselective and Stereospecific Reactions 219
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
6 Chemical Reactivity and Mechanisms 229
6.1 Enthalpy 230
6.2 Entropy 233
6.3 Gibbs Free Energy 235
WorldLinks Explosives 236
WorldLinks Do Living Organisms Violate the Second Law of Thermodynamics? 238
6.4 Equilibria 238
6.5 Kinetics 240
BioLinks Nitroglycerin: An Explosive with Medicinal Properties 243
WorldLinks Beer Making 244
6.6 Energy Diagrams 245
6.7 Nucleophiles and Electrophiles 248
6.8 Mechanisms and Arrow Pushing 252
6.9 Combining the Patterns of Arrow Pushing 257
6.10 Drawing Curved Arrows 259
6.11 Carbocation Rearrangements 262
6.12 Reversible and Irreversible Reaction Arrows 264
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
7 Substitution Reactions 277
7.1 Introduction to Substitution Reactions 278
7.2 Alkyl Halides 279
7.3 Possible Mechanisms for Substitution Reactions 283
7.4 The S N 2 Mechanism 285
BioLinks Pharmacology and Drug Design 291
7.5 Nucleophilic Strength in S N 2 Reactions 293
BioLinks S N 2 Reactions in Biological Systems--Methylation 293
7.6 The S N 1 Mechanism 295
7.7 Solvent Effects in Substitution Reactions 301
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems * Integrated Problems Challenge Problems
8 Alkenes: Structure and Preparation via Elimination Reactions 313
8.1 Introduction to Elimination Reactions 314
8.2 Stereoisomerism in Alkenes 314
BioLinks Phototherapy Treatment for Neonatal Jaundice 317
8.3 Stability of Alkenes and Cycloalkenes 319
8.4 Possible Mechanisms for Elimination Reactions 321
8.5 The E2 Mechanism 323
8.6 Regiochemical and Stereochemical Outcomes for E2 Reactions 325
8.7 The E1 Mechanism 335
8.8 Predicting Products: Substitution vs. Elimination 342
8.9 Substitution and Elimination Reactions with Other Substrates 348
8.10 Synthesis Strategies - Substitution and Elimination 352
BioLinks Radiolabeled Compounds in Diagnostic Medicine 356
SpecialTopic Kinetic Isotope Effects 361
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
9 Addition Reactions of Alkenes 371
9.1 Introduction to Addition Reactions 372
9.2 Alkenes in Nature and in Industry 373
WorldLinks Pheromones to Control Insect Populations 373
9.3 Nomenclature of Alkenes 374
9.4 Addition vs. Elimination: A Thermodynamic Perspective 376
9.5 Hydrohalogenation 377
WorldLinks Cationic Polymerization and Polystyrene 384
9.6 Acid-Catalyzed Hydration 385
9.7 Oxymercuration-Demercuration 389
9.8 Hydroboration-Oxidation 390
9.9 Catalytic Hydrogenation 396
WorldLinks Partially Hydrogenated Fats and Oils 401
9.10 Halogenation and Halohydrin Formation 402
9.11 Anti Dihydroxylation 406
9.12 Syn Dihydroxylation 409
9.13 Oxidative Cleavage 411
9.14 Predicting the Products of an Addition Reaction 413
9.15 Synthesis Strategies 415
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
10 Alkynes 431
10.1 Introduction to Alkynes 432
BioLinks The Role of Molecular Rigidity 434
WorldLinks Conducting Organic Polymers 435
10.2 Nomenclature of Alkynes 435
10.3 Acidity of Acetylene and Terminal Alkynes 437
10.4 Preparation of Alkynes 440
10.5 Reduction of Alkynes 442
10.6 Hydrohalogenation of Alkynes 445
10.7 Hydration of Alkynes 447
10.8 Halogenation of Alkynes 453
10.9 Ozonolysis of Alkynes 453
10.10 Alkylation of Terminal Alkynes 454
10.11 Synthesis Strategies 456
Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
11 Radical Reactions 467
11.1 Radicals 468
11.2 Common Patterns in Radical Mechanisms 473
11.3 Chlorination of Methane 476
11.4 Thermodynamic Considerations for Halogenation Reactions 480
11.5 Selectivity of Halogenation 482
11.6 Stereochemistry of Halogenation 485
11.7 Allylic Bromination 487
11.8 Atmospheric Chemistry and the Ozone Layer 490
WorldLinks Fighting Fires with Chemicals 492
11.9 Autooxidation and Antioxidants 493
BioLinks Why Is an Overdose of Acetaminophen Fatal? 495
11.10 Radical Addition of HBr: Anti-Markovnikov Addition 496
11.11 Radical Polymerization 500
11.12 Radical Processes in the Petrochemical Industry 502
11.13 Halogenation as a Synthetic Technique 502
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
12 Systematic Approach to Synthesis 511
12.1 One-Step Syntheses 512
12.2 Functional Group Transformations 513
12.3 Reactions That Change the Carbon Skeleton 517
BioLinks Vitamins 519
12.4 How to Approach a Synthesis Problem 520
BioLinks The Total Synthesis of Vitamin B 12 524
12.5 Multi- Step Synthesis and Retrosynthetic Analysis 526
WorldLinks Retrosynthetic Analysis 531
12.6 Green Chemistry 531
12.7 Practical Tips for Increasing Proficiency 532
BioLinks Total Synthesis of Taxol 533
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems Review of Reactions * 13 Alcohols and Phenols 541
13.1 Structure and Properties of Alcohols 542
BioLinks Chain Length as a Factor in Drug Design 546
13.2 Acidity of Alcohols and Phenols 547
13.3 Preparation of Alcohols via Substitution or Addition 550
13.4 Preparation of Alcohols via Reduction 551
13.5 Preparation of Diols 558
WorldLinks Antifreeze 559
13.6 Preparation of Alcohols via Grignard Reagents 559
13.7 Protection of Alcohols 564
13.8 Preparation of Phenols 565
13.9 Reactions of Alcohols: Substitution and Elimination 566
BioLinks Drug Metabolism 569
13.10 Reactions of Alcohols: Oxidation 571
13.11 Biological Redox Reactions 575
BioLinks Biological Oxidation of Methanol and Ethanol 577
13.12 Oxidation of Phenol 577
13.13 Synthesis Strategies 579
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder...
1.1 Introduction to Organic Chemistry 2
1.2 The Structural Theory of Matter 3
1.3 Electrons, Bonds, and Lewis Structures 4
1.4 Identifying Formal Charges 7
1.5 Induction and Polar Covalent Bonds 8
1.6 Reading Bond- Line Structures 11
1.7 Atomic Orbitals 14
1.8 Valence Bond Theory 17
1.9 Molecular Orbital Theory 18
1.10 Hybridized Atomic Orbitals 20
1.11 Predicting Molecular Geometry: VSEPR Theory 26
1.12 Dipole Moments and Molecular Polarity 30
1.13 Intermolecular Forces and Physical Properties 33
WorldLinks Biomimicry and Gecko Feet 37
BioLinks Drug- Receptor Interactions 38
1.14 Solubility 39
BioLinks Propofol: The Importance of Drug Solubility 40
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
2 Molecular Representations 49
2.1 Molecular Representations 50
2.2 Bond- Line Structures 52
2.3 Identifying Functional Groups 54
BioLinks Marine Natural Products 55
2.4 Carbon Atoms with Formal Charges 57
2.5 Identifying Lone Pairs 57
2.6 Three- Dimensional Bond- Line Structures 60
BioLinks The Opioids 61
2.7 Introduction to Resonance 62
2.8 Curved Arrows 64
2.9 Formal Charges in Resonance Structures 66
2.10 Drawing Resonance Structures via Pattern Recognition 68
2.11 Assessing the Relative Importance of Resonance Structures 73
2.12 The Resonance Hybrid 77
2.13 Delocalized and Localized Lone Pairs 79
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
3 Acids and Bases 91
3.1 Introduction to Brønsted- Lowry Acids and Bases 92
3.2 Flow of Electron Density: Curved- Arrow Notation 92
BioLinks Antacids and Heartburn 94
3.3 Brønsted- Lowry Acidity: Quantitative Perspective 95
BioLinks Drug Distribution and pK a 101
3.4 Brønsted- Lowry Acidity: Qualitative Perspective 102
3.5 Brønsted- Lowry Acidity: Assessing the Relative Acidity of Cationic Acids 113
3.6 Position of Equilibrium and Choice of Reagents 118
3.7 Leveling Effect 121
3.8 Solvating Effects 122
3.9 Counterions 123
WorldLinks Baking Soda versus Baking Powder 123
3.10 Lewis Acids and Bases 124
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
4 Alkanes and Cycloalkanes 137
4.1 Introduction to Alkanes 138
4.2 Nomenclature of Alkanes 138
WorldLinks Pheromones: Chemical Messengers 142
BioLinks Naming Drugs 150
4.3 Constitutional Isomers of Alkanes 151
4.4 Relative Stability of Isomeric Alkanes 152
4.5 Sources and Uses of Alkanes 153
WorldLinks An Introduction to Polymers 155
4.6 Drawing Newman Projections 155
4.7 Conformational Analysis of Ethane and Propane 157
4.8 Conformational Analysis of Butane 159
BioLinks Drugs and Their Conformations 163
4.9 Cycloalkanes 163
BioLinks Cyclopropane as an Inhalation Anesthetic 165
4.10 Conformations of Cyclohexane 166
4.11 Drawing Chair Conformations 167
4.12 Monosubstituted Cyclohexane 169
4.13 Disubstituted Cyclohexane 171
4.14 cis-trans Stereoisomerism 175
4.15 Polycyclic Systems 176
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
5 Stereoisomerism 187
5.1 Overview of Isomerism 188
5.2 Introduction to Stereoisomerism 189
WorldLinks The Sense of Smell 194
5.3 Designating Configuration Using the Cahn-Ingold-Prelog System 194
BioLinks Chiral Drugs 199
5.4 Optical Activity 200
5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers 206
5.6 Symmetry and Chirality 209
5.7 Fischer Projections 213
5.8 Conformationally Mobile Systems 215
5.9 Chirality without a Chiral Center 216
5.10 Resolution of Racemic Mixtures 217
5.11 Asymmetric Synthesis: Stereoselective and Stereospecific Reactions 219
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
6 Chemical Reactivity and Mechanisms 229
6.1 Enthalpy 230
6.2 Entropy 233
6.3 Gibbs Free Energy 235
WorldLinks Explosives 236
WorldLinks Do Living Organisms Violate the Second Law of Thermodynamics? 238
6.4 Equilibria 238
6.5 Kinetics 240
BioLinks Nitroglycerin: An Explosive with Medicinal Properties 243
WorldLinks Beer Making 244
6.6 Energy Diagrams 245
6.7 Nucleophiles and Electrophiles 248
6.8 Mechanisms and Arrow Pushing 252
6.9 Combining the Patterns of Arrow Pushing 257
6.10 Drawing Curved Arrows 259
6.11 Carbocation Rearrangements 262
6.12 Reversible and Irreversible Reaction Arrows 264
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
7 Substitution Reactions 277
7.1 Introduction to Substitution Reactions 278
7.2 Alkyl Halides 279
7.3 Possible Mechanisms for Substitution Reactions 283
7.4 The S N 2 Mechanism 285
BioLinks Pharmacology and Drug Design 291
7.5 Nucleophilic Strength in S N 2 Reactions 293
BioLinks S N 2 Reactions in Biological Systems--Methylation 293
7.6 The S N 1 Mechanism 295
7.7 Solvent Effects in Substitution Reactions 301
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems * Integrated Problems Challenge Problems
8 Alkenes: Structure and Preparation via Elimination Reactions 313
8.1 Introduction to Elimination Reactions 314
8.2 Stereoisomerism in Alkenes 314
BioLinks Phototherapy Treatment for Neonatal Jaundice 317
8.3 Stability of Alkenes and Cycloalkenes 319
8.4 Possible Mechanisms for Elimination Reactions 321
8.5 The E2 Mechanism 323
8.6 Regiochemical and Stereochemical Outcomes for E2 Reactions 325
8.7 The E1 Mechanism 335
8.8 Predicting Products: Substitution vs. Elimination 342
8.9 Substitution and Elimination Reactions with Other Substrates 348
8.10 Synthesis Strategies - Substitution and Elimination 352
BioLinks Radiolabeled Compounds in Diagnostic Medicine 356
SpecialTopic Kinetic Isotope Effects 361
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
9 Addition Reactions of Alkenes 371
9.1 Introduction to Addition Reactions 372
9.2 Alkenes in Nature and in Industry 373
WorldLinks Pheromones to Control Insect Populations 373
9.3 Nomenclature of Alkenes 374
9.4 Addition vs. Elimination: A Thermodynamic Perspective 376
9.5 Hydrohalogenation 377
WorldLinks Cationic Polymerization and Polystyrene 384
9.6 Acid-Catalyzed Hydration 385
9.7 Oxymercuration-Demercuration 389
9.8 Hydroboration-Oxidation 390
9.9 Catalytic Hydrogenation 396
WorldLinks Partially Hydrogenated Fats and Oils 401
9.10 Halogenation and Halohydrin Formation 402
9.11 Anti Dihydroxylation 406
9.12 Syn Dihydroxylation 409
9.13 Oxidative Cleavage 411
9.14 Predicting the Products of an Addition Reaction 413
9.15 Synthesis Strategies 415
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
10 Alkynes 431
10.1 Introduction to Alkynes 432
BioLinks The Role of Molecular Rigidity 434
WorldLinks Conducting Organic Polymers 435
10.2 Nomenclature of Alkynes 435
10.3 Acidity of Acetylene and Terminal Alkynes 437
10.4 Preparation of Alkynes 440
10.5 Reduction of Alkynes 442
10.6 Hydrohalogenation of Alkynes 445
10.7 Hydration of Alkynes 447
10.8 Halogenation of Alkynes 453
10.9 Ozonolysis of Alkynes 453
10.10 Alkylation of Terminal Alkynes 454
10.11 Synthesis Strategies 456
Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
11 Radical Reactions 467
11.1 Radicals 468
11.2 Common Patterns in Radical Mechanisms 473
11.3 Chlorination of Methane 476
11.4 Thermodynamic Considerations for Halogenation Reactions 480
11.5 Selectivity of Halogenation 482
11.6 Stereochemistry of Halogenation 485
11.7 Allylic Bromination 487
11.8 Atmospheric Chemistry and the Ozone Layer 490
WorldLinks Fighting Fires with Chemicals 492
11.9 Autooxidation and Antioxidants 493
BioLinks Why Is an Overdose of Acetaminophen Fatal? 495
11.10 Radical Addition of HBr: Anti-Markovnikov Addition 496
11.11 Radical Polymerization 500
11.12 Radical Processes in the Petrochemical Industry 502
11.13 Halogenation as a Synthetic Technique 502
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
12 Systematic Approach to Synthesis 511
12.1 One-Step Syntheses 512
12.2 Functional Group Transformations 513
12.3 Reactions That Change the Carbon Skeleton 517
BioLinks Vitamins 519
12.4 How to Approach a Synthesis Problem 520
BioLinks The Total Synthesis of Vitamin B 12 524
12.5 Multi- Step Synthesis and Retrosynthetic Analysis 526
WorldLinks Retrosynthetic Analysis 531
12.6 Green Chemistry 531
12.7 Practical Tips for Increasing Proficiency 532
BioLinks Total Synthesis of Taxol 533
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems Review of Reactions * 13 Alcohols and Phenols 541
13.1 Structure and Properties of Alcohols 542
BioLinks Chain Length as a Factor in Drug Design 546
13.2 Acidity of Alcohols and Phenols 547
13.3 Preparation of Alcohols via Substitution or Addition 550
13.4 Preparation of Alcohols via Reduction 551
13.5 Preparation of Diols 558
WorldLinks Antifreeze 559
13.6 Preparation of Alcohols via Grignard Reagents 559
13.7 Protection of Alcohols 564
13.8 Preparation of Phenols 565
13.9 Reactions of Alcohols: Substitution and Elimination 566
BioLinks Drug Metabolism 569
13.10 Reactions of Alcohols: Oxidation 571
13.11 Biological Redox Reactions 575
BioLinks Biological Oxidation of Methanol and Ethanol 577
13.12 Oxidation of Phenol 577
13.13 Synthesis Strategies 579
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder...
Details
| Erscheinungsjahr: | 2022 |
|---|---|
| Fachbereich: | Organische Chemie |
| Genre: | Chemie |
| Rubrik: | Naturwissenschaften & Technik |
| Medium: | Taschenbuch |
| Seiten: | 1296 |
| Inhalt: | 1392 S. |
| ISBN-13: | 9781119820833 |
| ISBN-10: | 1119820839 |
| Sprache: | Englisch |
| Herstellernummer: | 1W119820830 |
| Einband: | Kartoniert / Broschiert |
| Autor: | Klein, David R. |
| Auflage: | 4. Auflage |
| Hersteller: | Wiley John + Sons |
| Maße: | 276 x 216 x 52 mm |
| Von/Mit: | David R. Klein |
| Erscheinungsdatum: | 22.09.2022 |
| Gewicht: | 2,939 kg |
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