Organic Chemistry, International Adaptation
4. Auflage September 2022
1392 Seiten, Softcover
Lehrbuch
ISBN:
978-1-119-82083-3
John Wiley & Sons
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.
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 Review * Practice Problems Integrated Problems * Challenge Problems
14 Ethers and Epoxides; Thiols and Sulfides 597
14.1 Introduction to Ethers 598
14.2 Nomenclature of Ethers 598
14.3 Structure and Properties of Ethers 600
BioLinks Ethers as Inhalation Anesthetics 601
14.4 Crown Ethers 602
WorldLinks Chelating Agents in the Food Industry and in Medicine 604
14.5 Preparation of Ethers 605
14.6 Reactions of Ethers 608
14.7 Nomenclature of Epoxides 611
BioLinks Epothilones as Novel Anticancer Agents 612
14.8 Preparation of Epoxides 612
BioLinks Active Metabolites and Drug Interactions 615
14.9 Enantioselective Epoxidation 615
14.10 Ring- Opening Reactions of Epoxides 617
WorldLinks Ethylene Oxide as a Sterilizing Agent for Sensitive Medical Equipment 620
BioLinks Cigarette Smoke and Carcinogenic Epoxides 624
14.11 Thiols and Sulfides 625
14.12 Synthesis Strategies Involving Epoxides 629
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
15 Infrared Spectroscopy and Mass Spectrometry 647
15.1 Introduction to Spectroscopy 648
WorldLinks Microwave Ovens 650
15.2 IR Spectroscopy 650
BioLinks IR Thermal Imaging for Cancer Detection 651
15.3 Signal Characteristics: Wavenumber 652
15.4 Signal Characteristics: Intensity 657
WorldLinks IR Spectroscopy for Testing Blood Alcohol Levels 659
15.5 Signal Characteristics: Shape 659
15.6 Analyzing an IR Spectrum 663
15.7 Using IR Spectroscopy to Distinguish between Two Compounds 668
15.8 Introduction to Mass Spectrometry 669
WorldLinks Mass Spectrometry for Detecting Explosives 671
15.9 Analyzing the (M) +* Peak 672
15.10 Analyzing the (M+1) +* Peak 673
15.11 Analyzing the (M+2) +* Peak 675
15.12 Analyzing the Fragments 677
15.13 High- Resolution Mass Spectrometry 680
15.14 Gas Chromatography- Mass Spectrometry 682
15.15 Liquid Chromatography-Mass Spectrometry 682
15.16 Mass Spectrometry of Large Biomolecules 683
WorldLinks Medical Applications of Mass Spectrometry 683
15.17 Hydrogen Deficiency Index: Degrees of Unsaturation 684
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
16 Nuclear Magnetic Resonance Spectroscopy 695
16.1 Introduction to NMR Spectroscopy 696
16.2 Acquiring a 1 H NMR Spectrum 698
16.3 Characteristics of a 1 H NMR Spectrum 699
16.4 Number of Signals 700
16.5 Chemical Shift 706
16.6 Integration 713
16.7 Multiplicity 716
16.8 Drawing the Expected 1 H NMR Spectrum of a Compound 724
16.9 Using 1 H NMR Spectroscopy to Distinguish between Compounds 726
BioLinks Detection of Impurities in Heparin Sodium Using 1 H NMR Spectroscopy 728
16.10 Analyzing a 1 H NMR Spectrum 729
16.11 Acquiring a 13 C NMR Spectrum 732
16.12 Chemical Shifts in 13 C NMR Spectroscopy 732
16.13 DEPT 13 C NMR Spectroscopy 735
BioLinks Magnetic Resonance Imaging (MRI) 738
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
17 Conjugated Pi Systems and Pericyclic Reactions 749
17.1 Classes of Dienes 750
17.2 Conjugated Dienes 751
17.3 Molecular Orbital Theory 753
17.4 Electrophilic Addition 757
17.5 Thermodynamic Control vs. Kinetic Control 760
WorldLinks Natural and Synthetic Rubbers 763
17.6 An Introduction to Pericyclic Reactions 764
17.7 Diels-Alder Reactions 765
17.8 MO Description of Cycloadditions 771
17.9 Electrocyclic Reactions 774
17.10 Sigmatropic Rearrangements 779
BioLinks The Photoinduced Biosynthesis of Vitamin D 781
17.11 Other Pericyclic Reactions 782
17.12 UV-Vis Spectroscopy 784
WorldLinks Sunscreens 788
17.13 Photoreductions and Photorearrangements 788
17.14 Color 792
WorldLinks Bleach 792
17.15 Chemistry of Vision 793
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
18 Aromatic Compounds 803
18.1 Introduction to Aromatic Compounds 804
WorldLinks What Is Coal? 805
18.2 Nomenclature of Benzene Derivatives 805
18.3 Structure of Benzene 808
18.4 Stability of Benzene 809
WorldLinks Molecular Cages 813
18.5 Aromatic Compounds Other Than Benzene 816
BioLinks The Development of Nonsedating Antihistamines 821
18.6 Reactions at the Benzylic Position 823
18.7 Reduction of Benzene and Its Derivatives 828
18.8 Spectroscopy of Aromatic Compounds 830
WorldLinks Buckyballs and Nanotubes 833
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
19 Aromatic Substitution Reactions 843
19.1 Introduction to Electrophilic Aromatic Substitution 844
19.2 Halogenation 844
BioLinks Halogenation in Drug Design 847
19.3 Sulfonation 848
WorldLinks What Are Those Colors in Fruity Pebbles? 849
19.4 Nitration 850
BioLinks The Discovery of Prodrugs 851
19.5 Friedel-Crafts Alkylation 852
19.6 Friedel-Crafts Acylation 855
19.7 Activating Groups 856
19.8 Deactivating Groups 860
19.9 Halogens: The Exception 862
19.10 Determining the Directing Effects of a Substituent 863
19.11 Multiple Substituents 867
19.12 Synthesis Strategies 872
19.13 Nucleophilic Aromatic Substitution 878
19.14 Elimination-Addition 880
19.15 Identifying the Mechanism of an Aromatic Substitution Reaction 882
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
20 Aldehydes and Ketones 895
20.1 Introduction to Aldehydes and Ketones 896
20.2 Nomenclature 897
20.3 Preparation of Aldehydes and Ketones: A Review 899
20.4 Introduction to Nucleophilic Addition Reactions 900
20.5 Oxygen Nucleophiles 903
BioLinks Acetals as Prodrugs 909
20.6 Nitrogen Nucleophiles 911
WorldLinks Beta- Carotene and Vision 915
20.7 Hydrolysis of Acetals, Imines, and Enamines 919
BioLinks Prodrugs 922
20.8 Sulfur Nucleophiles 922
20.9 Hydrogen Nucleophiles 923
20.10 Carbon Nucleophiles 924
WorldLinks Organic Cyanide Compounds in Nature 927
20.11 Baeyer- Villiger Oxidation of Aldehydes and Ketones 933
20.12 Synthesis Strategies 935
20.13 Spectroscopic Analysis of Aldehydes and Ketones 938
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
21 Carboxylic Acids and Their Derivatives 951
21.1 Introduction to Carboxylic Acids 952
21.2 Nomenclature of Carboxylic Acids 952
21.3 Structure and Properties of Carboxylic Acids 954
21.4 Preparation of Carboxylic Acids 957
21.5 Reactions of Carboxylic Acids 958
21.6 Introduction to Carboxylic Acid Derivatives 959
BioLinks Sedatives 961
21.7 Reactivity of Carboxylic Acid Derivatives 963
21.8 Preparation and Reactions of Acid Chlorides 970
21.9 Preparation and Reactions of Acid Anhydrides 975
BioLinks How Does Aspirin Work? 977
21.10 Preparation of Esters 978
21.11 Reactions of Esters 979
WorldLinks How Soap Is Made 980
BioLinks Esters as Prodrugs 981
21.12 Preparation and Reactions of Amides 984
WorldLinks Polyesters and Polyamides 985
BioLinks Beta-Lactam Antibiotics 988
21.13 Preparation and Reactions of Nitriles 989
21.14 Synthesis Strategies 992
21.15 Spectroscopy of Carboxylic Acids and Their Derivatives 997
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
22 Alpha Carbon Chemistry: Enols and Enolates 1009
22.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates 1010
22.2 Alpha Halogenation of Enols and Enolates 1017
22.3 Aldol Reactions 1022
WorldLinks Muscle Power 1025
22.4 Claisen Condensations 1033
22.5 Alkylation of the Alpha Position 1035
22.6 Conjugate Addition Reactions 1044
BioLinks Glutathione Conjugation and Biochemical Michael Reactions 1046
22.7 Synthesis Strategies 1050
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
23 Amines 1067
23.1 Introduction to Amines 1068
BioLinks Drug Metabolism Studies 1069
23.2 Nomenclature of Amines 1069
23.3 Properties of Amines 1072
BioLinks Fortunate Side Effects 1073
WorldLinks Chemical Warfare Among Ants 1077
23.4 Preparation of Amines: A Review 1078
23.5 Preparation of Amines via Substitution Reactions 1079
23.6 Preparation of Amines via Reductive Amination 1082
23.7 Synthesis Strategies 1084
23.8 Acylation of Amines 1087
23.9 Hofmann Elimination 1088
23.10 Reactions of Amines with Nitrous Acid 1091
23.11 Reactions of Aryl Diazonium Ions 1093
23.12 Nitrogen Heterocycles 1097
BioLinks H 2 -Receptor Antagonists and the Development of Cimetidine 1098
23.13 Spectroscopy of Amines 1100
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
24 Introduction to Organometallic Compounds 1113
24.1 General Properties of Organometallic Compounds 1114
24.2 Organolithium and Organomagnesium Compounds 1115
24.3 Lithium Dialkyl Cuprates (Gilman Reagents) 1118
24.4 The Simmons-Smith Reaction and Carbenoids 1122
24.5 Stille Coupling 1125
24.6 Suzuki Coupling 1131
24.7 Negishi Coupling 1136
24.8 The Heck Reaction 1141
24.9 Sonogashira Coupling 1146
24.10 Hiyama Coupling 1151
24.11 Alkene Metathesis 1154
WorldLinks Improving Biodiesel via Alkene Metathesis 1159
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
25 Carbohydrates 1175
25.1 Introduction to Carbohydrates 1176
25.2 Classification of Monosaccharides 1176
25.3 Configuration of Aldoses 1179
25.4 Configuration of Ketoses 1180
25.5 Cyclic Structures of Monosaccharides 1182
25.6 Reactions of Monosaccharides 1189
25.7 Disaccharides 1196
BioLinks Lactose Intolerance 1199
WorldLinks Artificial Sweeteners 1200
25.8 Polysaccharides 1201
25.9 Amino Sugars 1202
25.10 N-Glycosides 1203
BioLinks Aminoglycoside Antibiotics 1204
BioLinks Erythromycin Biosynthesis 1208
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
26 Amino Acids, Peptides, and Proteins 1217
26.1 Introduction to Amino Acids, Peptides, and Proteins 1218
26.2 Structure and Properties of Amino Acids 1219
WorldLinks Nutrition and Sources of Amino Acids 1221
WorldLinks Forensic Chemistry and Fingerprint Detection 1225
26.3 Amino Acid Synthesis 1226
26.4 Structure of Peptides 1230
BioLinks Polypeptide Antibiotics 1235
26.5 Sequencing a Peptide 1236
26.6 Peptide Synthesis 1239
26.7 Protein Structure 1247
BioLinks Diseases Caused by Misfolded Proteins 1250
26.8 Protein Function 1250
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
27 Lipids 1261
27.1 Introduction to Lipids 1262
27.2 Waxes 1263
27.3 Triglycerides 1263
27.4 Reactions of Triglycerides 1267
WorldLinks Soaps Versus Synthetic Detergents 1271
27.5 Phospholipids 1275
BioLinks Polyether Antibiotics 1278
27.6 Steroids 1279
BioLinks Cholesterol and Heart Disease 1282
BioLinks Anabolic Steroids and Competitive Sports 1284
27.7 Prostaglandins 1285
BioLinks NSAIDs and COX-2 Inhibitors 1286
27.8 Terpenes 1287
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
28 Synthetic Polymers* 28.1 Introduction to Synthetic Polymers
28.2 Nomenclature of Synthetic Polymers
28.3 Copolymers
28.4 Polymer Classification by Reaction Type
28.5 Polymer Classification by Mode of Assembly
28.6 Polymer Classification by Structure
28.7 Polymer Classification by Properties
WorldLinks Safety Glass and Car Windshields
28.8 Polymer Recycling
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
Appendix A: Nomenclature of Polyfunctional Compounds A1
Appendix B: Multiple Choice Questions A5
Glossary G1
Index I1
Selected Answers*
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 Review * Practice Problems Integrated Problems * Challenge Problems
14 Ethers and Epoxides; Thiols and Sulfides 597
14.1 Introduction to Ethers 598
14.2 Nomenclature of Ethers 598
14.3 Structure and Properties of Ethers 600
BioLinks Ethers as Inhalation Anesthetics 601
14.4 Crown Ethers 602
WorldLinks Chelating Agents in the Food Industry and in Medicine 604
14.5 Preparation of Ethers 605
14.6 Reactions of Ethers 608
14.7 Nomenclature of Epoxides 611
BioLinks Epothilones as Novel Anticancer Agents 612
14.8 Preparation of Epoxides 612
BioLinks Active Metabolites and Drug Interactions 615
14.9 Enantioselective Epoxidation 615
14.10 Ring- Opening Reactions of Epoxides 617
WorldLinks Ethylene Oxide as a Sterilizing Agent for Sensitive Medical Equipment 620
BioLinks Cigarette Smoke and Carcinogenic Epoxides 624
14.11 Thiols and Sulfides 625
14.12 Synthesis Strategies Involving Epoxides 629
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
15 Infrared Spectroscopy and Mass Spectrometry 647
15.1 Introduction to Spectroscopy 648
WorldLinks Microwave Ovens 650
15.2 IR Spectroscopy 650
BioLinks IR Thermal Imaging for Cancer Detection 651
15.3 Signal Characteristics: Wavenumber 652
15.4 Signal Characteristics: Intensity 657
WorldLinks IR Spectroscopy for Testing Blood Alcohol Levels 659
15.5 Signal Characteristics: Shape 659
15.6 Analyzing an IR Spectrum 663
15.7 Using IR Spectroscopy to Distinguish between Two Compounds 668
15.8 Introduction to Mass Spectrometry 669
WorldLinks Mass Spectrometry for Detecting Explosives 671
15.9 Analyzing the (M) +* Peak 672
15.10 Analyzing the (M+1) +* Peak 673
15.11 Analyzing the (M+2) +* Peak 675
15.12 Analyzing the Fragments 677
15.13 High- Resolution Mass Spectrometry 680
15.14 Gas Chromatography- Mass Spectrometry 682
15.15 Liquid Chromatography-Mass Spectrometry 682
15.16 Mass Spectrometry of Large Biomolecules 683
WorldLinks Medical Applications of Mass Spectrometry 683
15.17 Hydrogen Deficiency Index: Degrees of Unsaturation 684
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
16 Nuclear Magnetic Resonance Spectroscopy 695
16.1 Introduction to NMR Spectroscopy 696
16.2 Acquiring a 1 H NMR Spectrum 698
16.3 Characteristics of a 1 H NMR Spectrum 699
16.4 Number of Signals 700
16.5 Chemical Shift 706
16.6 Integration 713
16.7 Multiplicity 716
16.8 Drawing the Expected 1 H NMR Spectrum of a Compound 724
16.9 Using 1 H NMR Spectroscopy to Distinguish between Compounds 726
BioLinks Detection of Impurities in Heparin Sodium Using 1 H NMR Spectroscopy 728
16.10 Analyzing a 1 H NMR Spectrum 729
16.11 Acquiring a 13 C NMR Spectrum 732
16.12 Chemical Shifts in 13 C NMR Spectroscopy 732
16.13 DEPT 13 C NMR Spectroscopy 735
BioLinks Magnetic Resonance Imaging (MRI) 738
Review of Concepts and Vocabulary * SkillBuilder Review Practice Problems * Integrated Problems * Challenge Problems
17 Conjugated Pi Systems and Pericyclic Reactions 749
17.1 Classes of Dienes 750
17.2 Conjugated Dienes 751
17.3 Molecular Orbital Theory 753
17.4 Electrophilic Addition 757
17.5 Thermodynamic Control vs. Kinetic Control 760
WorldLinks Natural and Synthetic Rubbers 763
17.6 An Introduction to Pericyclic Reactions 764
17.7 Diels-Alder Reactions 765
17.8 MO Description of Cycloadditions 771
17.9 Electrocyclic Reactions 774
17.10 Sigmatropic Rearrangements 779
BioLinks The Photoinduced Biosynthesis of Vitamin D 781
17.11 Other Pericyclic Reactions 782
17.12 UV-Vis Spectroscopy 784
WorldLinks Sunscreens 788
17.13 Photoreductions and Photorearrangements 788
17.14 Color 792
WorldLinks Bleach 792
17.15 Chemistry of Vision 793
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
18 Aromatic Compounds 803
18.1 Introduction to Aromatic Compounds 804
WorldLinks What Is Coal? 805
18.2 Nomenclature of Benzene Derivatives 805
18.3 Structure of Benzene 808
18.4 Stability of Benzene 809
WorldLinks Molecular Cages 813
18.5 Aromatic Compounds Other Than Benzene 816
BioLinks The Development of Nonsedating Antihistamines 821
18.6 Reactions at the Benzylic Position 823
18.7 Reduction of Benzene and Its Derivatives 828
18.8 Spectroscopy of Aromatic Compounds 830
WorldLinks Buckyballs and Nanotubes 833
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
19 Aromatic Substitution Reactions 843
19.1 Introduction to Electrophilic Aromatic Substitution 844
19.2 Halogenation 844
BioLinks Halogenation in Drug Design 847
19.3 Sulfonation 848
WorldLinks What Are Those Colors in Fruity Pebbles? 849
19.4 Nitration 850
BioLinks The Discovery of Prodrugs 851
19.5 Friedel-Crafts Alkylation 852
19.6 Friedel-Crafts Acylation 855
19.7 Activating Groups 856
19.8 Deactivating Groups 860
19.9 Halogens: The Exception 862
19.10 Determining the Directing Effects of a Substituent 863
19.11 Multiple Substituents 867
19.12 Synthesis Strategies 872
19.13 Nucleophilic Aromatic Substitution 878
19.14 Elimination-Addition 880
19.15 Identifying the Mechanism of an Aromatic Substitution Reaction 882
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
20 Aldehydes and Ketones 895
20.1 Introduction to Aldehydes and Ketones 896
20.2 Nomenclature 897
20.3 Preparation of Aldehydes and Ketones: A Review 899
20.4 Introduction to Nucleophilic Addition Reactions 900
20.5 Oxygen Nucleophiles 903
BioLinks Acetals as Prodrugs 909
20.6 Nitrogen Nucleophiles 911
WorldLinks Beta- Carotene and Vision 915
20.7 Hydrolysis of Acetals, Imines, and Enamines 919
BioLinks Prodrugs 922
20.8 Sulfur Nucleophiles 922
20.9 Hydrogen Nucleophiles 923
20.10 Carbon Nucleophiles 924
WorldLinks Organic Cyanide Compounds in Nature 927
20.11 Baeyer- Villiger Oxidation of Aldehydes and Ketones 933
20.12 Synthesis Strategies 935
20.13 Spectroscopic Analysis of Aldehydes and Ketones 938
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
21 Carboxylic Acids and Their Derivatives 951
21.1 Introduction to Carboxylic Acids 952
21.2 Nomenclature of Carboxylic Acids 952
21.3 Structure and Properties of Carboxylic Acids 954
21.4 Preparation of Carboxylic Acids 957
21.5 Reactions of Carboxylic Acids 958
21.6 Introduction to Carboxylic Acid Derivatives 959
BioLinks Sedatives 961
21.7 Reactivity of Carboxylic Acid Derivatives 963
21.8 Preparation and Reactions of Acid Chlorides 970
21.9 Preparation and Reactions of Acid Anhydrides 975
BioLinks How Does Aspirin Work? 977
21.10 Preparation of Esters 978
21.11 Reactions of Esters 979
WorldLinks How Soap Is Made 980
BioLinks Esters as Prodrugs 981
21.12 Preparation and Reactions of Amides 984
WorldLinks Polyesters and Polyamides 985
BioLinks Beta-Lactam Antibiotics 988
21.13 Preparation and Reactions of Nitriles 989
21.14 Synthesis Strategies 992
21.15 Spectroscopy of Carboxylic Acids and Their Derivatives 997
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
22 Alpha Carbon Chemistry: Enols and Enolates 1009
22.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates 1010
22.2 Alpha Halogenation of Enols and Enolates 1017
22.3 Aldol Reactions 1022
WorldLinks Muscle Power 1025
22.4 Claisen Condensations 1033
22.5 Alkylation of the Alpha Position 1035
22.6 Conjugate Addition Reactions 1044
BioLinks Glutathione Conjugation and Biochemical Michael Reactions 1046
22.7 Synthesis Strategies 1050
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
23 Amines 1067
23.1 Introduction to Amines 1068
BioLinks Drug Metabolism Studies 1069
23.2 Nomenclature of Amines 1069
23.3 Properties of Amines 1072
BioLinks Fortunate Side Effects 1073
WorldLinks Chemical Warfare Among Ants 1077
23.4 Preparation of Amines: A Review 1078
23.5 Preparation of Amines via Substitution Reactions 1079
23.6 Preparation of Amines via Reductive Amination 1082
23.7 Synthesis Strategies 1084
23.8 Acylation of Amines 1087
23.9 Hofmann Elimination 1088
23.10 Reactions of Amines with Nitrous Acid 1091
23.11 Reactions of Aryl Diazonium Ions 1093
23.12 Nitrogen Heterocycles 1097
BioLinks H 2 -Receptor Antagonists and the Development of Cimetidine 1098
23.13 Spectroscopy of Amines 1100
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
24 Introduction to Organometallic Compounds 1113
24.1 General Properties of Organometallic Compounds 1114
24.2 Organolithium and Organomagnesium Compounds 1115
24.3 Lithium Dialkyl Cuprates (Gilman Reagents) 1118
24.4 The Simmons-Smith Reaction and Carbenoids 1122
24.5 Stille Coupling 1125
24.6 Suzuki Coupling 1131
24.7 Negishi Coupling 1136
24.8 The Heck Reaction 1141
24.9 Sonogashira Coupling 1146
24.10 Hiyama Coupling 1151
24.11 Alkene Metathesis 1154
WorldLinks Improving Biodiesel via Alkene Metathesis 1159
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
25 Carbohydrates 1175
25.1 Introduction to Carbohydrates 1176
25.2 Classification of Monosaccharides 1176
25.3 Configuration of Aldoses 1179
25.4 Configuration of Ketoses 1180
25.5 Cyclic Structures of Monosaccharides 1182
25.6 Reactions of Monosaccharides 1189
25.7 Disaccharides 1196
BioLinks Lactose Intolerance 1199
WorldLinks Artificial Sweeteners 1200
25.8 Polysaccharides 1201
25.9 Amino Sugars 1202
25.10 N-Glycosides 1203
BioLinks Aminoglycoside Antibiotics 1204
BioLinks Erythromycin Biosynthesis 1208
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
26 Amino Acids, Peptides, and Proteins 1217
26.1 Introduction to Amino Acids, Peptides, and Proteins 1218
26.2 Structure and Properties of Amino Acids 1219
WorldLinks Nutrition and Sources of Amino Acids 1221
WorldLinks Forensic Chemistry and Fingerprint Detection 1225
26.3 Amino Acid Synthesis 1226
26.4 Structure of Peptides 1230
BioLinks Polypeptide Antibiotics 1235
26.5 Sequencing a Peptide 1236
26.6 Peptide Synthesis 1239
26.7 Protein Structure 1247
BioLinks Diseases Caused by Misfolded Proteins 1250
26.8 Protein Function 1250
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
27 Lipids 1261
27.1 Introduction to Lipids 1262
27.2 Waxes 1263
27.3 Triglycerides 1263
27.4 Reactions of Triglycerides 1267
WorldLinks Soaps Versus Synthetic Detergents 1271
27.5 Phospholipids 1275
BioLinks Polyether Antibiotics 1278
27.6 Steroids 1279
BioLinks Cholesterol and Heart Disease 1282
BioLinks Anabolic Steroids and Competitive Sports 1284
27.7 Prostaglandins 1285
BioLinks NSAIDs and COX-2 Inhibitors 1286
27.8 Terpenes 1287
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
28 Synthetic Polymers* 28.1 Introduction to Synthetic Polymers
28.2 Nomenclature of Synthetic Polymers
28.3 Copolymers
28.4 Polymer Classification by Reaction Type
28.5 Polymer Classification by Mode of Assembly
28.6 Polymer Classification by Structure
28.7 Polymer Classification by Properties
WorldLinks Safety Glass and Car Windshields
28.8 Polymer Recycling
Review of Reactions * Review of Concepts and Vocabulary SkillBuilder Review * Practice Problems Integrated Problems * Challenge Problems
Appendix A: Nomenclature of Polyfunctional Compounds A1
Appendix B: Multiple Choice Questions A5
Glossary G1
Index I1
Selected Answers*
