Organic Chemistry, 4th Edition
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
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2 Molecular Representations 50
2.1 Molecular Representations 51
2.2 Drawing Bond-Line Structures 53
2.3 Identifying Functional Groups 55
BioLinks Marine Natural Products 56
2.4 Carbon Atoms with Formal Charges 58
2.5 Identifying Lone Pairs 58
2.6 Three-Dimensional Bond-Line Structures 61
BioLinks The Opioids 62
2.7 Introduction to Resonance 63
2.8 Curved Arrows 65
2.9 Formal Charges in Resonance Structures 68
2.10 Drawing Resonance Structures via Pattern Recognition 70
2.11 Assessing the Relative Importance of Resonance Structures 75
2.12 The Resonance Hybrid 79
2.13 Delocalized and Localized Lone Pairs 81
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3 Acids and Bases 93
3.1 Introduction to Brønsted-Lowry Acids and Bases 94
3.2 Flow of Electron Density: Curved-Arrow Notation 94
BioLinks Antacids and Heartburn 96
3.3 Brønsted-Lowry Acidity: Comparing pKa values 97
BioLinks Drug Distribution and pKa 103
3.4 Brønsted-Lowry Acidity: Factors Affecting the Stability of Anions 104
3.5 Brønsted-Lowry Acidity: Assessing the Relative Acidity of Cationic Acids 115
3.6 Position of Equilibrium and Choice of Reagents 120
3.7 Leveling Effect 123
3.8 Solvating Effects 124
3.9 Counterions 125
WorldLinks Baking Soda versus Baking Powder 125
3.10 Lewis Acids and Bases 126
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4 Alkanes and Cycloalkanes 138
4.1 Introduction to Alkanes 139
4.2 Nomenclature of Alkanes 139
WorldLinks Pheromones: Chemical Messengers 143
BioLinks Naming Drugs 151
4.3 Constitutional Isomers of Alkanes 152
4.4 Relative Stability of Isomeric Alkanes 153
4.5 Sources and Uses of Alkanes 154
WorldLinks An Introduction to Polymers 156
4.6 Drawing Newman Projections 156
4.7 Conformational Analysis of Ethane and Propane 158
4.8 Conformational Analysis of Butane 160
BioLinks Drugs and Their Conformations 164
4.9 Cycloalkanes 164
BioLinks Cyclopropane as an Inhalation Anesthetic 166
4.10 Conformations of Cyclohexane 167
4.11 Drawing Chair Conformations 168
4.12 Monosubstituted Cyclohexane 170
4.13 Disubstituted Cyclohexane 172
4.14 cis-trans Stereoisomerism 176
4.15 Polycyclic Systems 177
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5 Stereoisomerism 188
5.1 Overview of Isomerism 189
5.2 Introduction to Stereoisomerism 190
WorldLinks The Sense of Smell 195
5.3 Designating Configuration Using the Cahn-Ingold-Prelog System 195
BioLinks Chiral Drugs 200
5.4 Optical Activity 201
5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers 207
5.6 Symmetry and Chirality 210
5.7 Fischer Projections 214
5.8 Conformationally Mobile Systems 216
5.9 Chiral Compounds that Lack a Chiral Center 217
5.10 Resolution of Enantiomers 218
5.11 E and Z Designations for Diastereomeric Alkenes 220
BioLinks Phototherapy Treatment for Neonatal Jaundice 222
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6 Chemical Reactivity and Mechanisms 233
6.1 Enthalpy 234
6.2 Entropy 237
6.3 Gibbs Free Energy 239
WorldLinks Explosives 240
WorldLinks Do Living Organisms Violate the Second Law of Thermodynamics? 242
6.4 Equilibria 242
6.5 Kinetics 244
BioLinks Nitroglycerin: An Explosive with Medicinal Properties 247
WorldLinks Beer Making 248
6.6 Reading Energy Diagrams 249
6.7 Nucleophiles and Electrophiles 252
6.8 Mechanisms and Arrow Pushing 256
6.9 Combining the Patterns of Arrow Pushing 261
6.10 Drawing Curved Arrows 263
6.11 Carbocation Rearrangements 266
6.12 Reversible and Irreversible Reaction Arrows 268
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7 Alkyl Halides: Nucleophilic Substitution and Elimination Reactions 280
7.1 Introduction to Substitution and Elimination Reactions 281
7.2 Nomenclature and Uses of Alkyl Halides 282
7.3 SN2 Reactions 286
BioLinks Pharmacology and Drug Design 292
7.4 Nucleophilic Strength in SN2 Reactions 294
BioLinks SN2 Reactions in Biological Systems—Methylation 295
7.5 Introduction to E2 Reactions 296
7.6 Stability of Alkenes and Cycloalkenes 299
7.7 Regiochemical and Stereochemical Outcomes for E2 Reactions 301
7.8 Unimolecular Reactions (SN1 and E1) 311
7.9 Predicting Products: Substitution vs. Elimination 320
7.10 Substitution and Elimination Reactions with Other Substrates 327
7.11 Synthesis Strategies 331
BioLinks Radiolabeled Compounds in Diagnostic Medicine 338
7.12 Solvent Effects in Substitution Reactions 339
SpecialTopic Kinetic Isotope Effects 343
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8 Addition Reactions of Alkenes 356
8.1 Introduction to Addition Reactions 357
8.2 Alkenes in Nature and in Industry 358
WorldLinks Pheromones to Control Insect Populations 358
8.3 Nomenclature of Alkenes 359
8.4 Addition vs. Elimination: A Thermodynamic Perspective 361
8.5 Hydrohalogenation 363
WorldLinks Cationic Polymerization and Polystyrene 370
8.6 Acid-Catalyzed Hydration 371
8.7 Oxymercuration-Demercuration 375
8.8 Hydroboration-Oxidation 376
8.9 Catalytic Hydrogenation 382
WorldLinks Partially Hydrogenated Fats and Oils 387
8.10 Halogenation and Halohydrin Formation 388
8.11 Anti Dihydroxylation 392
8.12 Syn Dihydroxylation 395
8.13 Oxidative Cleavage 396
8.14 Predicting the Products of an Addition Reaction 398
8.15 Synthesis Strategies 400
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9 Alkynes 417
9.1 Introduction to Alkynes 418
BioLinks The Role of Molecular Rigidity 420
WorldLinks Conducting Organic Polymers 421
9.2 Nomenclature of Alkynes 421
9.3 Acidity of Acetylene and Terminal Alkynes 423
9.4 Preparation of Alkynes 426
9.5 Reduction of Alkynes 428
9.6 Hydrohalogenation of Alkynes 431
9.7 Hydration of Alkynes 433
9.8 Halogenation of Alkynes 439
9.9 Ozonolysis of Alkynes 439
9.10 Alkylation of Terminal Alkynes 440
9.11 Synthesis Strategies 442
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10 Radical Reactions 454
10.1 Radicals 455
10.2 Common Patterns in Radical Mechanisms 460
10.3 Chlorination of Methane 463
10.4 Thermodynamic Considerations for Halogenation Reactions 467
10.5 Selectivity of Halogenation 469
10.6 Stereochemistry of Halogenation 472
10.7 Allylic Bromination 474
10.8 Atmospheric Chemistry and the Ozone Layer 477
WorldLinks Fighting Fires with Chemicals 479
10.9 Autooxidation and Antioxidants 480
BioLinks Why is an Overdose of Acetaminophen Fatal? 482
10.10 Radical Addition of HBr: Anti-Markovnikov Addition 483
10.11 Radical Polymerization 487
10.12 Radical Processes in the Petrochemical Industry 489
10.13 Halogenation as a Synthetic Technique 489
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11 Synthesis 499
11.1 One-Step Syntheses 500
11.2 Functional Group Transformations 501
11.3 Reactions That Change the Carbon Skeleton 505
BioLinks Vitamins 507
11.4 How to Approach a Synthesis Problem 508
BioLinks The Total Synthesis of Vitamin B12 512
11.5 Multi-step Synthesis and Retrosynthetic Analysis 514
WorldLinks Retrosynthetic Analysis 519
11.6 Green Chemistry 519
11.7 Practical Tips for Increasing Proficiency 520
BioLinks Total Synthesis of Taxol 521
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12 Alcohols and Phenols 529
12.1 Structure and Properties of Alcohols 530
BioLinks Chain Length as a Factor in Drug Design 534
12.2 Acidity of Alcohols and Phenols 535
12.3 Preparation of Alcohols via Substitution or Addition 538
12.4 Preparation of Alcohols via Reduction 539
12.5 Preparation of Diols 546
WorldLinks Antifreeze 547
12.6 Preparation of Alcohols via Grignard Reagents 547
12.7 Protection of Alcohols 552
12.8 Preparation of Phenols 553
12.9 Reactions of Alcohols: Substitution and Elimination 554
BioLinks Drug Metabolism 557
12.10 Reactions of Alcohols: Oxidation 559
12.11 Biological Redox Reactions 563
BioLinks Biological Oxidation of Methanol and Ethanol 565
12.12 Oxidation of Phenol 565
12.13 Synthesis Strategies 567
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13 Ethers and Epoxides; Thiols and Sulfides 585
13.1 Introduction to Ethers 586
13.2 Nomenclature of Ethers 586
13.3 Structure and Properties of Ethers 588
BioLinks Ethers as Inhalation Anesthetics 589
13.4 Crown Ethers 590
WorldLinks Chelating Agents in the Food Industry and in Medicine 592
13.5 Preparation of Ethers 593
13.6 Reactions of Ethers 596
13.7 Nomenclature of Epoxides 599
BioLinks Epothilones as Novel Anticancer Agents 600
13.8 Preparation of Epoxides 600
BioLinks Active Metabolites and Drug Interactions 603
13.9 Enantioselective Epoxidation 603
13.10 Ring-Opening Reactions of Epoxides 605
WorldLinks Ethylene Oxide as a Sterilizing Agent for Sensitive Medical Equipment 608
BioLinks Cigarette Smoke and Carcinogenic Epoxides 612
13.11 Thiols and Sulfides 613
13.12 Synthesis Strategies Involving Epoxides 617
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14 Infrared Spectroscopy and Mass Spectrometry 636
14.1 Introduction to Spectroscopy 637
WorldLinks Microwave Ovens 639
14.2 IR Spectroscopy 639
BioLinks IR Thermal Imaging for Cancer Detection 640
14.3 Signal Characteristics: Wavenumber 641
14.4 Signal Characteristics: Intensity 646
WorldLinks IR Spectroscopy for Testing Blood Alcohol Levels 648
14.5 Signal Characteristics: Shape 648
14.6 Analyzing an IR Spectrum 652
14.7 Using IR Spectroscopy to Distinguish between Two Compounds 657
14.8 Introduction to Mass Spectrometry 658
WorldLinks Mass Spectrometry for Detecting Explosives 660
14.9 Analyzing the (M)+• Peak 661
14.10 Analyzing the (M+1)+• Peak 662
14.11 Analyzing the (M+2)+• Peak 664
14.12 Analyzing the Fragments 665
14.13 High-Resolution Mass Spectrometry 668
14.14 Gas Chromatography–Mass Spectrometry 670
14.15 Mass Spectrometry of Large Biomolecules 671
BioLinks Medical Applications of Mass Spectrometry 671
14.16 Hydrogen Deficiency Index: Degrees of Unsaturation 672
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15 Nuclear Magnetic Resonance Spectroscopy 684
15.1 Introduction to NMR Spectroscopy 685
15.2 Acquiring a 1H NMR Spectrum 687
15.3 Characteristics of a 1H NMR Spectrum 688
15.4 Number of Signals 689
15.5 Chemical Shift 695
15.6 Integration 702
15.7 Multiplicity 705
15.8 Drawing the Expected 1H NMR Spectrum of a Compound 713
15.9 Using 1H NMR Spectroscopy to Distinguish between Compounds 715
BioLinks Detection of Impurities in Heparin Sodium Using 1H NMR Spectroscopy 717
15.10 Analyzing a 1H NMR Spectrum 718
15.11 Acquiring a 13C NMR Spectrum 721
15.12 Chemical Shifts in 13C NMR Spectroscopy 721
15.13 DEPT 13C NMR Spectroscopy 724
BioLinks Magnetic Resonance Imaging (MRI) 727
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16 Conjugated Pi Systems and Pericyclic Reactions 738
16.1 Classes of Dienes 739
16.2 Conjugated Dienes 740
16.3 Molecular Orbital Theory 742
16.4 Electrophilic Addition 746
16.5 Thermodynamic Control vs. Kinetic Control 749
WorldLinks Natural and Synthetic Rubbers 752
16.6 An Introduction to Pericyclic Reactions 753
16.7 Diels–Alder Reactions 754
16.8 MO Description of Cycloadditions 760
16.9 Electrocyclic Reactions 763
16.10 Sigmatropic Rearrangements 768
BioLinks The Photoinduced Biosynthesis of Vitamin D 770
16.11 UV-Vis Spectroscopy 771
WorldLinks Sunscreens 775
16.12 Color 776
WorldLinks Bleach 777
16.13 Chemistry of Vision 777
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17 Aromatic Compounds 788
17.1 Introduction to Aromatic Compounds 789
WorldLinks What is Coal? 790
17.2 Nomenclature of Benzene Derivatives 790
17.3 Structure of Benzene 793
17.4 Stability of Benzene 794
WorldLinks Molecular Cages 798
17.5 Aromatic Compounds Other Than Benzene 801
BioLinks The Development of Nonsedating Antihistamines 806
17.6 Reactions at the Benzylic Position 808
17.7 Reduction of Benzene and Its Derivatives 813
17.8 Spectroscopy of Aromatic Compounds 815
WorldLinks Buckyballs and Nanotubes 818
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18 Aromatic Substitution Reactions 828
18.1 Introduction to Electrophilic Aromatic Substitution 829
18.2 Halogenation 829
BioLinks Halogenation in Drug Design 832
18.3 Sulfonation 833
WorldLinks What Are Those Colors in Fruity Pebbles? 834
18.4 Nitration 835
BioLinks The Discovery of Prodrugs 837
18.5 Friedel–Crafts Alkylation 838
18.6 Friedel–Crafts Acylation 840
18.7 Activating Groups 842
18.8 Deactivating Groups 846
18.9 Halogens: The Exception 848
18.10 Determining the Directing Effects of a Substituent 850
18.11 Multiple Substituents 853
18.12 Synthesis Strategies 859
18.13 Nucleophilic Aromatic Substitution 866
18.14 Elimination-Addition 868
18.15 Identifying the Mechanism of an Aromatic Substitution Reaction 870
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19 Aldehydes and Ketones 884
19.1 Introduction to Aldehydes and Ketones 885
19.2 Nomenclature 886
19.3 Preparing Aldehydes and Ketones: A Review 888
19.4 Introduction to Nucleophilic Addition Reactions 889
19.5 Oxygen Nucleophiles 892
BioLinks Acetals as Prodrugs 898
19.6 Nitrogen Nucleophiles 900
WorldLinks Beta-Carotene and Vision 904
19.7 Hydrolysis of Acetals, Imines, and Enamines 908
BioLinks Prodrugs 911
19.8 Sulfur Nucleophiles 911
19.9 Hydrogen Nucleophiles 912
19.10 Carbon Nucleophiles 913
WorldLinks Organic Cyanide Compounds in Nature 916
19.11 Baeyer–Villiger Oxidation of Aldehydes and Ketones 921
19.12 Synthesis Strategies 922
19.13 Spectroscopic Analysis of Aldehydes and Ketones 925
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20 Carboxylic Acids and Their Derivatives 938
20.1 Introduction to Carboxylic Acids 939
20.2 Nomenclature of Carboxylic Acids 939
20.3 Structure and Properties of Carboxylic Acids 941
20.4 Preparation of Carboxylic Acids 944
20.5 Reactions of Carboxylic Acids 945
20.6 Introduction to Carboxylic Acid Derivatives 946
BioLinks Sedatives 948
20.7 Reactivity of Carboxylic Acid Derivatives 950
20.8 Preparation and Reactions of Acid Chlorides 957
20.9 Preparation and Reactions of Acid Anhydrides 962
BioLinks How Does Aspirin Work? 964
20.10 Preparation of Esters 965
20.11 Reactions of Esters 966
WorldLinks How Soap is Made 967
BioLinks Esters as Prodrugs 968
20.12 Preparation and Reactions of Amides 971
WorldLinks Polyesters and Polyamides 972
BioLinks Beta-Lactam Antibiotics 975
20.13 Preparation and Reactions of Nitriles 976
20.14 Synthesis Strategies 979
20.15 Spectroscopy of Carboxylic Acids and Their Derivatives 984
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21 Alpha Carbon Chemistry: Enols and Enolates 996
21.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates 997
21.2 Alpha Halogenation of Enols and Enolates 1004
21.3 Aldol Reactions 1009
WorldLinks Muscle Power 1012
21.4 Claisen Condensations 1020
21.5 Alkylation of the Alpha Position 1022
21.6 Conjugate Addition Reactions 1031
BioLinks Glutathione Conjugation and Biological Michael Reactions 1033
21.7 Synthesis Strategies 1037
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22 Amines 1054
22.1 Introduction to Amines 1055
BioLinks Drug Metabolism Studies 1056
22.2 Nomenclature of Amines 1056
22.3 Properties of Amines 1059
BioLinks Fortunate Side Effects 1060
WorldLinks Chemical Warfare Among Ants 1064
22.4 Preparation of Amines: A Review 1065
22.5 Preparation of Amines via Substitution Reactions 1066
22.6 Preparation of Amines via Reductive Amination 1069
22.7 Synthesis Strategies 1071
22.8 Acylation of Amines 1074
22.9 Hofmann Elimination 1075
22.10 Reactions of Amines with Nitrous Acid 1078
22.11 Reactions of Aryl Diazonium Ions 1080
22.12 Nitrogen Heterocycles 1084
BioLinks H2-Receptor Antagonists and the Development of Cimetidine 1085
22.13 Spectroscopy of Amines 1087
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23 Introduction to Organometallic Compounds 1100
23.1 General Properties of Organometallic Compounds 1101
23.2 Organolithium and Organomagnesium Compounds 1102
23.3 Lithium Dialkyl Cuprates (Gilman Reagents) 1105
23.4 The Simmons–Smith Reaction and Carbenoids 1109
23.5 Stille Coupling 1112
23.6 Suzuki Coupling 1117
23.7 Negishi Coupling 1123
23.8 The Heck Reaction 1128
23.9 Alkene Metathesis 1133
WorldLinks Improving Biodiesel via Alkene Metathesis 1138
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24 Carbohydrates 1153
24.1 Introduction to Carbohydrates 1154
24.2 Classification of Monosaccharides 1154
24.3 Configuration of Aldoses 1157
24.4 Configuration of Ketoses 1158
24.5 Cyclic Structures of Monosaccharides 1160
24.6 Reactions of Monosaccharides 1167
24.7 Disaccharides 1174
BioLinks Lactose Intolerance 1177
WorldLinks Artificial Sweeteners 1178
24.8 Polysaccharides 1179
24.9 Amino Sugars 1180
24.10 N-Glycosides 1181
BioLinks Aminoglycoside Antibiotics 1182
BioLinks Erythromycin Biosynthesis 1186
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25 Amino Acids, Peptides, and Proteins 1194
25.1 Introduction to Amino Acids, Peptides, and Proteins 1195
25.2 Structure and Properties of Amino Acids 1196
WorldLinks Nutrition and Sources of Amino Acids 1198
WorldLinks Forensic Chemistry and Fingerprint Detection 1202
25.3 Amino Acid Synthesis 1203
25.4 Structure of Peptides 1207
BioLinks Polypeptide Antibiotics 1212
25.5 Sequencing a Peptide 1213
25.6 Peptide Synthesis 1216
25.7 Protein Structure 1224
BioLinks Diseases Caused by Misfolded Proteins 1227
25.8 Protein Function 1227
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26 Lipids 1238
26.1 Introduction to Lipids 1239
26.2 Waxes 1240
26.3 Triglycerides 1241
26.4 Reactions of Triglycerides 1244
WorldLinks Soaps Versus Synthetic Detergents 1249
26.5 Phospholipids 1253
BioLinks Polyether Antibiotics 1256
26.6 Steroids 1257
BioLinks Cholesterol and Heart Disease 1260
BioLinks Anabolic Steroids and Competitive Sports 1263
26.7 Prostaglandins 1263
BioLinks NSAIDs and COX-2 Inhibitors 1265
26.8 Terpenes 1266
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27 Synthetic Polymers 1277
27.1 Introduction to Synthetic Polymers 1278
27.2 Nomenclature of Synthetic Polymers 1279
27.3 Copolymers 1280
27.4 Polymer Classification by Reaction Type 1281
27.5 Polymer Classification by Mode of Assembly 1289
27.6 Polymer Classification by Structure 1291
27.7 Polymer Classification by Properties 1294
WorldLinks Safety Glass and Car Windshields 1295
27.8 Polymer Recycling 1296
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Appendix: Nomenclature of Polyfunctional Compounds A–1
Selected Answers ANS–1
Glossary G–1
Index I–1
