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简介
With a reputation for outstanding scientific quality, Organic Chemistry by G. Marc Loudon is a textbook that students will actually want to read. This much-anticipated fourth edition continues its predecessors' popular and unique mechanistic approach within a functional group framework. Enhanced biological and biochemical material makes it ideal for chemistry majors as well as pre-medical and pre-pharmacy students taking a full-year, sophomore- level course. Loudon's excellent use of language and reader-friendly style transform organic chemistry into a logical, understandable, and exciting subject for students.In use at undergraduate and graduate schools of all levels, this authoritative yet accessible volume is packed with effective analogies that enliven and clarify rigorous discussions of important concepts. For example, Loudon uses a flute player jumping between musical octaves to explain transitions between quantum levels. An engaging detective with combined characteristics from Sherlock Holmes and James Bond depicts resonance structures. Thanks to humorous characters like Flick Flaskflinger and Professor Havno Scentz, problem-solving becomes simultaneously challenging and entertaining. Varying from the routine to the complex, Loudon's problems are renowned for their originality, their range of difficulty levels, and their ability to teach students to understand and predict organic reactivity rather than just memorize facts. In addition, Loudon blends biological, environmental, and industrial applications of organic chemistry into the body of the text-rather than separating them as "special topics"-giving students an integrated sense of the subject in its real-life context.Other FeaturesDT Uses a high-resolution 300 MHz spectra run specifically for this text in an easy-to-read format that makes splitting patterns very clear.DT Includes new sections on transition-metal organometallic chemistry, reactions of pyridoxal phosphate, combinatorial synthesis, and drug design.DT Emphasizes both Bronsted and Lewis acid-base chemistry and their associated curved-arrow notations.DT Provides more than 1,500 excellent in-text problems that challenge students to think and analyze rather than just memorize.DT Presents "boxed asides" with interesting historical vignettes and analogies that enrich the text.DT Utilizes extensive cross-references between important concepts, thus saving students trips to the index.DT Supplemented by a CD-ROM--"Dynamic Organic Chemistry"--containing original animations (Mac and Windows compatible).DT Accompanied by a comprehensive Study Guide and Solutions Manual, acclaimed as one of the best in the field. This combination guide/manual supplies not only answers but also detailed solutions to all text problems. Its "Study Guide Links" show students how to solve problems, provide shortcuts to mastering particular topics, and offer detailed discussions of concepts that students often find difficult. Full chapter outlines, a glossary of terms, and reaction reviews are provided.
目录
Preface p. xxv
About the Author p. xxxiii
Chemical Bonding and Chemical Structure p. 1
Introduction p. 1
Classical Theories of Chemical Bonding p. 3
Structures of Covalent Compounds p. 11
Resonance Structures p. 18
Wave Nature of the Electron p. 20
Electronic Structure of the Hydrogen Atom p. 21
Electronic Structures of More Complex Atoms p. 27
Another Look at the Covalent Bond: Molecular Orbitals p. 30
Hybrid Orbitals p. 35
Key Ideas in Chapter 1 p. 38
Additional Problems p. 39
Alkanes p. 43
Hydrocarbons p. 43
Unbranched Alkanes p. 45
Conformations of Alkanes p. 47
Constitutional Isomers and Nomenclature p. 53
Cycloalkanes and Skeletal Structures p. 62
Physical Properties of Alkanes p. 65
Combustion and Elemental Analysis p. 70
Occurrence and Use of Alkanes p. 73
Functional Groups, Compound Classes, and the "R" Notation p. 76
Key Ideas in Chapter 2 p. 78
Additional Problems p. 78
Acids and Bases: The Curved-Arrow Notation p. 82
Lewis Acid-Base Association Reactions p. 82
Electron-Pair Displacement Reactions p. 85
Review of the Curved-Arrow Notation p. 89
Bronsted-Lowry Acids and Bases p. 91
Free Energy and Chemical Equilibrium p. 96
Relationship of Structure to Acidity p. 99
Key Ideas in Chapter 3 p. 105
Additional Problems p. 106
Introduction to Alkenes: Structure and Reactivity p. 111
Structure and Bonding in Alkenes p. 111
Nomenclature of Alkenes p. 119
Unsaturation Number p. 126
Physical Properties of Alkenes p. 127
Relative Stabilities of Alkene Isomers p. 128
Addition Reactions of Alkenes p. 133
Addition of Hydrogen Halides to Alkenes p. 134
Reaction Rates p. 142
Catalysis p. 150
Key Ideas in Chapter 4 p. 155
Additional Problems p. 156
Addition Reactions of Alkenes p. 160
Reactions of Alkenes with Halogens p. 160
Writing Organic Reactions p. 164
Conversion of Alkenes Into Alcohols p. 165
Ozonolysis of Alkenes p. 173
Free-Radical Addition of Hydrogen Bromide to Alkenes p. 177
Polymers: Free-Radical Polymerization of Alkenes p. 190
Alkenes in the Chemical Industry p. 192
Key Ideas in Chapter 5 p. 195
Additional Problems p. 195
Principles of Stereochemistry p. 201
Enantiomers, Chirality, and Symmetry p. 201
Nomenclature of Enantiomers: The R,S System p. 206
Physical Properties of Enantiomers: Optical Activity p. 209
Racemates p. 213
Stereochemical Correlation p. 215
Diastereomers p. 217
Meso Compounds p. 221
Enantiomeric Resolution p. 224
Chiral Molecules Without Asymmetric Atoms p. 226
Conformational Stereoisomers p. 228
Fischer Projections p. 231
The Postulation of Tetrahedral Carbon p. 235
Key Ideas in Chapter 6 p. 239
Additional Problems p. 239
Cyclic Compounds: Stereochemistry of Reactions p. 244
Relative Stabilities of the Monocyclic Alkanes p. 244
Conformations of Cyclohexane p. 245
Monosubstituted Cyclohexanes: Conformational Analysis p. 253
Disubstituted Cyclohexanes p. 257
Cyclopentane, Cyclobutane, and Cyclopropane p. 265
Bicyclic and Polycyclic Compounds p. 268
Relative Reactivities of Stereoisomers p. 275
Reactions That Form Stereoisomers p. 278
Stereochemistry of Chemical Reactions p. 283
Key Ideas in Chapter 7 p. 293
Additional Problems p. 294
Introduction to Alkyl Halides, Alcohols, Ethers, Thiols, and Sulfides p. 301
Nomenclature p. 302
Structures p. 310
Effect of Molecular Polarity and Hydrogen Bonding on Physical Properties p. 311
Solvents in Organic Chemistry p. 316
Applications of Solubility and Solvation Principles p. 322
Acidity of Alcohols and Thiols p. 328
Basicity of Alcohols and Ethers p. 333
Grignard and Organolithium Reagents p. 334
Industrial Preparation and Use of Alkyl Halides, Alcohols, and Ethers p. 338
Key Ideas in Chapter 8 p. 346
Additional Problems p. 347
Chemistry of Alkyl Halides p. 351
An Overview of Nucleophilic Substitution and [beta]-Elimination Reactions p. 351
Equilibrium in Nucleophilic Substitution Reactions p. 356
Reaction Rates p. 357
The S[subscript N]2 Reaction p. 360
The E2 Reaction p. 371
The S[subscript N]1 and E1 Reactions p. 382
Summary of Substitution and Elimination Reactions of Alkyl Halides p. 391
Carbenes and Carbenoids p. 394
Key Ideas in Chapter 9 p. 399
Additional Problems p. 400
Chemistry of Alcohols and Thiols p. 408
Dehydration of Alcohols p. 408
Reactions of Alcohols with Hydrogen Halides p. 411
Sulfonate and Inorganic Ester Derivatives of Alcohols p. 414
Conversion of Alcohols into Alkyl Halides: Summary p. 422
Oxidation and Reduction in Organic Chemistry p. 423
Oxidation of Alcohols p. 430
Biological Oxidation of Ethanol p. 433
Chemical and Stereochemical Group Equivalence p. 436
Oxidation of Thiols p. 443
Synthesis of Alcohols p. 446
Design of Organic Synthesis p. 447
Key Ideas in Chapter 10 p. 449
Additional Problems p. 450
Chemistry of Ethers, Epoxides, Glycols, and Sulfides p. 455
Synthesis of Ethers and Sulfides p. 455
Synthesis of Epoxides p. 461
Cleavage of Ethers p. 464
Nucleophilic Substitution Reactions of Epoxides p. 467
Preparation and Oxidative Cleavage of Glycols p. 473
Oxonium and Sulfonium Salts p. 479
Neighboring-Group Participation: Intramolecular Reactions p. 481
Oxidation of Ethers and Sulfides p. 484
The Three Fundamental Operations of Organic Synthesis p. 485
Key Ideas in Chapter 11 p. 487
Additional Problems p. 488
Introduction to Spectroscopy: Infrared Spectroscopy and Mass Spectrometry p. 497
Introduction to Spectroscopy p. 497
Infrared Spectroscopy p. 502
Infrared Absorption and Chemical Structure p. 505
Functional-Group Infrared Absorptions p. 512
The Infrared Spectrometer p. 517
Introduction to Mass Spectrometry p. 518
Key Ideas in Chapter 12 p. 531
Additional Problems p. 531
Nuclear Magnetic Resonance Spectroscopy p. 539
An Overview of Proton NMR Spectroscopy p. 539
Physical Basis of NMR Spectroscopy p. 542
The NMR Spectrum: Chemical Shift and Integral p. 544
The NMR Spectrum: Spin-Spin Splitting p. 557
Complex NMR Spectra p. 566
USE of Deuterium in Proton NMR p. 573
Characteristic Functional-Group NMR Absorptions p. 574
NMR Spectroscopy of Dynamic Systems p. 581
Carbon NMR p. 584
Solving Structure Problems with Spectroscopy p. 591
The NMR Spectrometer p. 594
Other uses of NMR p. 596
Key Idens in Chapter 13 p. 597
Additional Problems p. 597
Chemistry of Alkynes p. 606
Nomenclature of Alkynes p. 606
Structure and Bonding In Alkynes p. 608
Physical Properties of Alkynes p. 611
Introduction to Addition Reac Hons of the Triple Bond p. 614
Conversion of Alkynes Into Aldehydes and Ketones p. 615
Reduction of Alkynes p. 620
Acidity of 1-Alkynes p. 623
Organic Synthesis Using Alkynes p. 627
Pheromones p. 628
Occurrence and use of Alkynes p. 630
Key Ideas in Chapter 14 p. 631
Additional Problems p. 632
Dienes, Resonance, and Aromaticity p. 637
Structure and Stability of Dienes p. 638
Ultraviolet Spectroscopy p. 642
The Diels-Alder Reaction p. 648
Addition of Hydrogen Halides to Conjugated Dienes p. 658
Diene Polymers p. 664
Resonance p. 666
Introduction to Aromatic Compounds p. 673
Key Ideas in Chapter 15 p. 684
Additional Problems p. 685
Chemistry of Benzene and Its Derivatives p. 694
Nomenclature of Benzene Derivatives p. 694
Physical Properties of Benzene Derivatives p. 697
Spectroscopy of Benzene Derivatives p. 698
Electrophilic Aromatic Substitution Reactions of Benzene p. 704
Electrophilic Aromatic Substitution Reactions of Substituted Benzenes p. 716
Hydrogenation of Benzene Derivatives p. 731
Source and Industrial use of Aromatic Hydrocarbons p. 732
Key Ideas in Chapter 16 p. 735
Additional Problems p. 735
Allylic and Benzylic Reactivity p. 743
Reactions Involving Allylic and Benzylic Carbocations p. 744
Reactions Involving Allylic and Benzylic Radicals p. 748
Reactions Involving Allylic and Benzylic Anions p. 753
Allylic and Benzylic S[subscript N]2 Reactions p. 757
Benzylic Oxidation of Alkylbenzenes p. 758
Terpenes p. 759
Key Ideas in Chapter 17 p. 766
Additional Problems p. 767
Chemistry of Aryl Halides, Vinylic Halides, and Phenols: Transition-Metal Catalysis p. 775
Lack of Reactivity of Vinylic and Aryl Halides Under S[subscript N]2 Conditions p. 776
Elimination Reactions of Vinylic Halides p. 778
Lack of Reactivity of Vinylic and Aryl Halides Under S[subscript N]1 Conditions p. 779
Nucleophilic Substitution Reactions of Aryl Halides p. 781
Transition-Metal Catalyzed Coupling Reactions p. 788
Acidity of Phenols p. 807
Oxidation of Phenols to Quinones p. 811
Electrophilic Aromatic Substitution Reactions of Phenols p. 815
Reactivity of the Aryl-Oxygen Bond p. 819
Industrial Preparation and use of Phenol p. 823
Key Ideas in Chapter 18 p. 824
Additional Problems p. 825
Chemistry of Aldehydes and Ketones: Carbonyl-Addition Reactions p. 836
Nomenclature of Aldehydes and Ketones p. 838
Physical Properties of Aldehydes and Ketones p. 842
Spectroscopy of Aldehydes and Ketones p. 843
Synthesis of Aldehydes and Ketones p. 851
Introduction to Aldehyde and Ketone Reactions p. 851
Basicity of Aldehydes and Ketones p. 852
Reversible Addition Reactions of Aldehydes and Ketones p. 855
Reduction of Aldehydes and Ketones to Alcohols p. 861
Reactions of Aldehydes and Ketones with Grignard and Related Reagents p. 865
Acetals and Their use as Protecting Groups p. 868
Reactions of Aldehydes and Ketones with Amines p. 874
Reduction of Carbonyl Groups to Methylene Groups p. 879
The Wittig Alkene Synthesis p. 881
Oxidation of Aldehydes to Carboxylic Acids p. 884
Manufacture and use of Aldehydes and Ketones p. 886
Key Ideas in Chapter 19 p. 887
Additional Problems p. 888
Chemistry of Carboxylic Acids p. 895
Nomenclature of Carboxylic Acids p. 895
Structure and Physical Properties of Carboxylic Acids p. 900
Spectroscopy of Carboxylic Acids p. 902
Acid-Base Properties of Carboxylic Acids p. 904
Fatty Acids, Soaps, and Detergents p. 908
Synthesis of Carboxylic Acids p. 910
Introduction to Carboxylic Acid Reactions p. 911
Conversion of Carboxylic Acids into Esters p. 913
Conversion of Carboxylic Acids into Acid Chlorides and Anhydrides p. 918
Reduction of Carboxylic Acids to Primary Alcohols p. 922
Decarboxylation of Carboxylic Acids p. 923
Key Ideas in Chapter 20 p. 926
Additional Problems p. 926
Chemistry of Carboxylic Acid Derivatives p. 934
Nomenclature and Classification of Carboxylic Acid Derivatives p. 934
Structures of Carboxylic Acid Derivatives p. 940
Physical Properties of Carboxylic Acid Derivatives p. 942
Spectroscopy of Carboxylic Acid Derivatives p. 944
Basicity of Carboxylic Acid Derivatives p. 949
Introduction to Reactions of Carboxylic Acid Derivatives p. 950
Hydrolysis of Carboxylic Acid Derivatives p. 951
Reactions of Carboxylic Acid Derivatives with Nucleophiles p. 963
Reduction of Carboxylic Acid Derivatives p. 969
Reactions of Carboxylic Acid Derivatives with Organometallic Reagents p. 977
Synthesis of Carboxylic Acid Derivatives p. 980
Use and Occurrence of Carboxylic Acids and Their Derivatives p. 982
Key Ideas in Chapter 21 p. 986
Additional Problems p. 987
Chemistry of Enolate Ions, Enols, and [alpha],[beta]-Unsaturated Carbonyl Compounds p. 997
Acidity of Carbonyl compounds p. 998
Enolization of Carbonyl Compounds p. 1003
[alpha]-Halogenation of Carbonyl Compounds p. 1007
Aldol Addition and Aldol Condensation p. 1014
Condensation Reactions Involving Ester Enolate Ions p. 1023
Biosynthesis of Fatty Acids p. 1032
Alkylation of Ester Enolate Ions p. 1035
Conjugate-Addition Reactions p. 1043
Reduction of [alpha],[beta]-Unsaturated Carbonyl Compounds p. 1052
Reactions of [alpha],[beta]-Unsaturated Carbonyl Compounds with Organometallic Reagents p. 1053
Organic Synthesis with Conjugate-Addition Reactions p. 1055
Key Ideas in Chapter 22 p. 1057
Additional Problems p. 1058
Chemistry of Amines p. 1069
Nomenclature of Amines p. 1070
Structure of Amines p. 1072
Physical Properties of Amines p. 1073
Spectroscopy of Amines p. 1074
Basicity and Acidity of Amines p. 1076
Quaternary Ammonium Salts p. 1083
Alkylation and Acylation Reactions of Amines p. 1083
Hofmann Elimination of Quaternary Ammonium Hydroxides p. 1088
Aromatic Substitution Reactions of Aniline Derivatives p. 1092
Diazotization: Reactions of Diazonium Ions p. 1094
Synthesis of Amines p. 1100
Use and Occurrence of Amines p. 1108
Key Ideas in Chapter 23 p. 1110
Additional Problems p. 1111
Chemistry of Naphthalene and the Aromatic Heterocycles p. 1120
Chemistry of Naphthalene p. 1122
Introduction to the Aromatic Heterocycles p. 1128
Chemistry of Furan, Pyrrole, and Thiophene p. 1135
Synthesis of Indoles p. 1140
Chemistry of Pyridine and Quinoline p. 1144
Occurrence of Heterocyclic Compounds p. 1161
Key Ideas in Chapter 24 p. 1162
Additional Problems p. 1163
Pericyclic Reactions p. 1172
Molecular Orbitals of Conjugated [pi]-Electron Systems p. 1175
Electrocyclic Reactions p. 1183
Cycloaddition Reactions p. 1183
Sigmatropic Reactions p. 1192
Summary of the Pericyclic Selection Rules p. 1203
Fluxional Molecules p. 1204
Formation of Vitamin D p. 1205
Key Ideas in Chapter 25 p. 1207
Additional Problems p. 1208
Amino Acids, Peptides, and Proteins p. 1215
Nomenclature of Amino Acids and Peptides p. 1216
Stereochemistry of the [alpha]-Amino Acids p. 1220
Acid-Base Properties of Amino Acids and Peptides p. 1221
Synthesis and Enantiomeric Resolution of [alpha]-Amino Acids p. 1229
Acylation and Esterification Reactions of Amino Acids p. 1232
Determination of Peptide Structure p. 1233
Solid-Phase Peptide Synthesis p. 1246
Combinatorial Chemistry p. 1255
Structures of Peptides and Proteins p. 1261
Enzymes: Biological Catalysts p. 1270
Occurrence of Peptides and Proteins p. 1279
Key Ideas in Chapter 26 p. 1280
Additional Problems p. 1281
Carbohydrates and Nucleic Acids p. 1291
Classification and Properties of Carbohydrates p. 1292
Structures of the Monosaccharides p. 1293
Mutarotation of Carbohydrates p. 1302
Base-Catalyzed Isomerization of Aldoses and Ketoses p. 1306
Glycosides p. 1308
Ether and Ester Derivatives of Carbohydrates p. 1311
Oxidation and Reduction Reactions of Carbohydrates p. 1314
Kiliani-Fischer Synthesis p. 1319
Proof of Glucose Stereochemistry p. 1320
Disaccharides and Polysaccharides p. 1326
Nucleosides, Nucleotides, and Nucleic Acids p. 1333
DNA, RNA, and the Genetic Code p. 1341
Key Ideas in Chapter 27 p. 1345
Additional Problems p. 1346
Appendixes p. 1
Substitutive Nomenclature of Organic Compounds p. 1
Infrared Absorptions of Organic Compounds p. 2
Proton NMR Chemical Shifts in Organic Compounds p. 5
[superscript 13]C NMR Chemical Shifts in Organic Compounds p. 7
Summary of Synthetic Methods p. 8
Reactions Used to Form Carbon-Carbon Bonds p. 13
Typical Acidities and Basicities of Organic Functional Groups p. 14
Credits p. 1
Index p. 1
About the Author p. xxxiii
Chemical Bonding and Chemical Structure p. 1
Introduction p. 1
Classical Theories of Chemical Bonding p. 3
Structures of Covalent Compounds p. 11
Resonance Structures p. 18
Wave Nature of the Electron p. 20
Electronic Structure of the Hydrogen Atom p. 21
Electronic Structures of More Complex Atoms p. 27
Another Look at the Covalent Bond: Molecular Orbitals p. 30
Hybrid Orbitals p. 35
Key Ideas in Chapter 1 p. 38
Additional Problems p. 39
Alkanes p. 43
Hydrocarbons p. 43
Unbranched Alkanes p. 45
Conformations of Alkanes p. 47
Constitutional Isomers and Nomenclature p. 53
Cycloalkanes and Skeletal Structures p. 62
Physical Properties of Alkanes p. 65
Combustion and Elemental Analysis p. 70
Occurrence and Use of Alkanes p. 73
Functional Groups, Compound Classes, and the "R" Notation p. 76
Key Ideas in Chapter 2 p. 78
Additional Problems p. 78
Acids and Bases: The Curved-Arrow Notation p. 82
Lewis Acid-Base Association Reactions p. 82
Electron-Pair Displacement Reactions p. 85
Review of the Curved-Arrow Notation p. 89
Bronsted-Lowry Acids and Bases p. 91
Free Energy and Chemical Equilibrium p. 96
Relationship of Structure to Acidity p. 99
Key Ideas in Chapter 3 p. 105
Additional Problems p. 106
Introduction to Alkenes: Structure and Reactivity p. 111
Structure and Bonding in Alkenes p. 111
Nomenclature of Alkenes p. 119
Unsaturation Number p. 126
Physical Properties of Alkenes p. 127
Relative Stabilities of Alkene Isomers p. 128
Addition Reactions of Alkenes p. 133
Addition of Hydrogen Halides to Alkenes p. 134
Reaction Rates p. 142
Catalysis p. 150
Key Ideas in Chapter 4 p. 155
Additional Problems p. 156
Addition Reactions of Alkenes p. 160
Reactions of Alkenes with Halogens p. 160
Writing Organic Reactions p. 164
Conversion of Alkenes Into Alcohols p. 165
Ozonolysis of Alkenes p. 173
Free-Radical Addition of Hydrogen Bromide to Alkenes p. 177
Polymers: Free-Radical Polymerization of Alkenes p. 190
Alkenes in the Chemical Industry p. 192
Key Ideas in Chapter 5 p. 195
Additional Problems p. 195
Principles of Stereochemistry p. 201
Enantiomers, Chirality, and Symmetry p. 201
Nomenclature of Enantiomers: The R,S System p. 206
Physical Properties of Enantiomers: Optical Activity p. 209
Racemates p. 213
Stereochemical Correlation p. 215
Diastereomers p. 217
Meso Compounds p. 221
Enantiomeric Resolution p. 224
Chiral Molecules Without Asymmetric Atoms p. 226
Conformational Stereoisomers p. 228
Fischer Projections p. 231
The Postulation of Tetrahedral Carbon p. 235
Key Ideas in Chapter 6 p. 239
Additional Problems p. 239
Cyclic Compounds: Stereochemistry of Reactions p. 244
Relative Stabilities of the Monocyclic Alkanes p. 244
Conformations of Cyclohexane p. 245
Monosubstituted Cyclohexanes: Conformational Analysis p. 253
Disubstituted Cyclohexanes p. 257
Cyclopentane, Cyclobutane, and Cyclopropane p. 265
Bicyclic and Polycyclic Compounds p. 268
Relative Reactivities of Stereoisomers p. 275
Reactions That Form Stereoisomers p. 278
Stereochemistry of Chemical Reactions p. 283
Key Ideas in Chapter 7 p. 293
Additional Problems p. 294
Introduction to Alkyl Halides, Alcohols, Ethers, Thiols, and Sulfides p. 301
Nomenclature p. 302
Structures p. 310
Effect of Molecular Polarity and Hydrogen Bonding on Physical Properties p. 311
Solvents in Organic Chemistry p. 316
Applications of Solubility and Solvation Principles p. 322
Acidity of Alcohols and Thiols p. 328
Basicity of Alcohols and Ethers p. 333
Grignard and Organolithium Reagents p. 334
Industrial Preparation and Use of Alkyl Halides, Alcohols, and Ethers p. 338
Key Ideas in Chapter 8 p. 346
Additional Problems p. 347
Chemistry of Alkyl Halides p. 351
An Overview of Nucleophilic Substitution and [beta]-Elimination Reactions p. 351
Equilibrium in Nucleophilic Substitution Reactions p. 356
Reaction Rates p. 357
The S[subscript N]2 Reaction p. 360
The E2 Reaction p. 371
The S[subscript N]1 and E1 Reactions p. 382
Summary of Substitution and Elimination Reactions of Alkyl Halides p. 391
Carbenes and Carbenoids p. 394
Key Ideas in Chapter 9 p. 399
Additional Problems p. 400
Chemistry of Alcohols and Thiols p. 408
Dehydration of Alcohols p. 408
Reactions of Alcohols with Hydrogen Halides p. 411
Sulfonate and Inorganic Ester Derivatives of Alcohols p. 414
Conversion of Alcohols into Alkyl Halides: Summary p. 422
Oxidation and Reduction in Organic Chemistry p. 423
Oxidation of Alcohols p. 430
Biological Oxidation of Ethanol p. 433
Chemical and Stereochemical Group Equivalence p. 436
Oxidation of Thiols p. 443
Synthesis of Alcohols p. 446
Design of Organic Synthesis p. 447
Key Ideas in Chapter 10 p. 449
Additional Problems p. 450
Chemistry of Ethers, Epoxides, Glycols, and Sulfides p. 455
Synthesis of Ethers and Sulfides p. 455
Synthesis of Epoxides p. 461
Cleavage of Ethers p. 464
Nucleophilic Substitution Reactions of Epoxides p. 467
Preparation and Oxidative Cleavage of Glycols p. 473
Oxonium and Sulfonium Salts p. 479
Neighboring-Group Participation: Intramolecular Reactions p. 481
Oxidation of Ethers and Sulfides p. 484
The Three Fundamental Operations of Organic Synthesis p. 485
Key Ideas in Chapter 11 p. 487
Additional Problems p. 488
Introduction to Spectroscopy: Infrared Spectroscopy and Mass Spectrometry p. 497
Introduction to Spectroscopy p. 497
Infrared Spectroscopy p. 502
Infrared Absorption and Chemical Structure p. 505
Functional-Group Infrared Absorptions p. 512
The Infrared Spectrometer p. 517
Introduction to Mass Spectrometry p. 518
Key Ideas in Chapter 12 p. 531
Additional Problems p. 531
Nuclear Magnetic Resonance Spectroscopy p. 539
An Overview of Proton NMR Spectroscopy p. 539
Physical Basis of NMR Spectroscopy p. 542
The NMR Spectrum: Chemical Shift and Integral p. 544
The NMR Spectrum: Spin-Spin Splitting p. 557
Complex NMR Spectra p. 566
USE of Deuterium in Proton NMR p. 573
Characteristic Functional-Group NMR Absorptions p. 574
NMR Spectroscopy of Dynamic Systems p. 581
Carbon NMR p. 584
Solving Structure Problems with Spectroscopy p. 591
The NMR Spectrometer p. 594
Other uses of NMR p. 596
Key Idens in Chapter 13 p. 597
Additional Problems p. 597
Chemistry of Alkynes p. 606
Nomenclature of Alkynes p. 606
Structure and Bonding In Alkynes p. 608
Physical Properties of Alkynes p. 611
Introduction to Addition Reac Hons of the Triple Bond p. 614
Conversion of Alkynes Into Aldehydes and Ketones p. 615
Reduction of Alkynes p. 620
Acidity of 1-Alkynes p. 623
Organic Synthesis Using Alkynes p. 627
Pheromones p. 628
Occurrence and use of Alkynes p. 630
Key Ideas in Chapter 14 p. 631
Additional Problems p. 632
Dienes, Resonance, and Aromaticity p. 637
Structure and Stability of Dienes p. 638
Ultraviolet Spectroscopy p. 642
The Diels-Alder Reaction p. 648
Addition of Hydrogen Halides to Conjugated Dienes p. 658
Diene Polymers p. 664
Resonance p. 666
Introduction to Aromatic Compounds p. 673
Key Ideas in Chapter 15 p. 684
Additional Problems p. 685
Chemistry of Benzene and Its Derivatives p. 694
Nomenclature of Benzene Derivatives p. 694
Physical Properties of Benzene Derivatives p. 697
Spectroscopy of Benzene Derivatives p. 698
Electrophilic Aromatic Substitution Reactions of Benzene p. 704
Electrophilic Aromatic Substitution Reactions of Substituted Benzenes p. 716
Hydrogenation of Benzene Derivatives p. 731
Source and Industrial use of Aromatic Hydrocarbons p. 732
Key Ideas in Chapter 16 p. 735
Additional Problems p. 735
Allylic and Benzylic Reactivity p. 743
Reactions Involving Allylic and Benzylic Carbocations p. 744
Reactions Involving Allylic and Benzylic Radicals p. 748
Reactions Involving Allylic and Benzylic Anions p. 753
Allylic and Benzylic S[subscript N]2 Reactions p. 757
Benzylic Oxidation of Alkylbenzenes p. 758
Terpenes p. 759
Key Ideas in Chapter 17 p. 766
Additional Problems p. 767
Chemistry of Aryl Halides, Vinylic Halides, and Phenols: Transition-Metal Catalysis p. 775
Lack of Reactivity of Vinylic and Aryl Halides Under S[subscript N]2 Conditions p. 776
Elimination Reactions of Vinylic Halides p. 778
Lack of Reactivity of Vinylic and Aryl Halides Under S[subscript N]1 Conditions p. 779
Nucleophilic Substitution Reactions of Aryl Halides p. 781
Transition-Metal Catalyzed Coupling Reactions p. 788
Acidity of Phenols p. 807
Oxidation of Phenols to Quinones p. 811
Electrophilic Aromatic Substitution Reactions of Phenols p. 815
Reactivity of the Aryl-Oxygen Bond p. 819
Industrial Preparation and use of Phenol p. 823
Key Ideas in Chapter 18 p. 824
Additional Problems p. 825
Chemistry of Aldehydes and Ketones: Carbonyl-Addition Reactions p. 836
Nomenclature of Aldehydes and Ketones p. 838
Physical Properties of Aldehydes and Ketones p. 842
Spectroscopy of Aldehydes and Ketones p. 843
Synthesis of Aldehydes and Ketones p. 851
Introduction to Aldehyde and Ketone Reactions p. 851
Basicity of Aldehydes and Ketones p. 852
Reversible Addition Reactions of Aldehydes and Ketones p. 855
Reduction of Aldehydes and Ketones to Alcohols p. 861
Reactions of Aldehydes and Ketones with Grignard and Related Reagents p. 865
Acetals and Their use as Protecting Groups p. 868
Reactions of Aldehydes and Ketones with Amines p. 874
Reduction of Carbonyl Groups to Methylene Groups p. 879
The Wittig Alkene Synthesis p. 881
Oxidation of Aldehydes to Carboxylic Acids p. 884
Manufacture and use of Aldehydes and Ketones p. 886
Key Ideas in Chapter 19 p. 887
Additional Problems p. 888
Chemistry of Carboxylic Acids p. 895
Nomenclature of Carboxylic Acids p. 895
Structure and Physical Properties of Carboxylic Acids p. 900
Spectroscopy of Carboxylic Acids p. 902
Acid-Base Properties of Carboxylic Acids p. 904
Fatty Acids, Soaps, and Detergents p. 908
Synthesis of Carboxylic Acids p. 910
Introduction to Carboxylic Acid Reactions p. 911
Conversion of Carboxylic Acids into Esters p. 913
Conversion of Carboxylic Acids into Acid Chlorides and Anhydrides p. 918
Reduction of Carboxylic Acids to Primary Alcohols p. 922
Decarboxylation of Carboxylic Acids p. 923
Key Ideas in Chapter 20 p. 926
Additional Problems p. 926
Chemistry of Carboxylic Acid Derivatives p. 934
Nomenclature and Classification of Carboxylic Acid Derivatives p. 934
Structures of Carboxylic Acid Derivatives p. 940
Physical Properties of Carboxylic Acid Derivatives p. 942
Spectroscopy of Carboxylic Acid Derivatives p. 944
Basicity of Carboxylic Acid Derivatives p. 949
Introduction to Reactions of Carboxylic Acid Derivatives p. 950
Hydrolysis of Carboxylic Acid Derivatives p. 951
Reactions of Carboxylic Acid Derivatives with Nucleophiles p. 963
Reduction of Carboxylic Acid Derivatives p. 969
Reactions of Carboxylic Acid Derivatives with Organometallic Reagents p. 977
Synthesis of Carboxylic Acid Derivatives p. 980
Use and Occurrence of Carboxylic Acids and Their Derivatives p. 982
Key Ideas in Chapter 21 p. 986
Additional Problems p. 987
Chemistry of Enolate Ions, Enols, and [alpha],[beta]-Unsaturated Carbonyl Compounds p. 997
Acidity of Carbonyl compounds p. 998
Enolization of Carbonyl Compounds p. 1003
[alpha]-Halogenation of Carbonyl Compounds p. 1007
Aldol Addition and Aldol Condensation p. 1014
Condensation Reactions Involving Ester Enolate Ions p. 1023
Biosynthesis of Fatty Acids p. 1032
Alkylation of Ester Enolate Ions p. 1035
Conjugate-Addition Reactions p. 1043
Reduction of [alpha],[beta]-Unsaturated Carbonyl Compounds p. 1052
Reactions of [alpha],[beta]-Unsaturated Carbonyl Compounds with Organometallic Reagents p. 1053
Organic Synthesis with Conjugate-Addition Reactions p. 1055
Key Ideas in Chapter 22 p. 1057
Additional Problems p. 1058
Chemistry of Amines p. 1069
Nomenclature of Amines p. 1070
Structure of Amines p. 1072
Physical Properties of Amines p. 1073
Spectroscopy of Amines p. 1074
Basicity and Acidity of Amines p. 1076
Quaternary Ammonium Salts p. 1083
Alkylation and Acylation Reactions of Amines p. 1083
Hofmann Elimination of Quaternary Ammonium Hydroxides p. 1088
Aromatic Substitution Reactions of Aniline Derivatives p. 1092
Diazotization: Reactions of Diazonium Ions p. 1094
Synthesis of Amines p. 1100
Use and Occurrence of Amines p. 1108
Key Ideas in Chapter 23 p. 1110
Additional Problems p. 1111
Chemistry of Naphthalene and the Aromatic Heterocycles p. 1120
Chemistry of Naphthalene p. 1122
Introduction to the Aromatic Heterocycles p. 1128
Chemistry of Furan, Pyrrole, and Thiophene p. 1135
Synthesis of Indoles p. 1140
Chemistry of Pyridine and Quinoline p. 1144
Occurrence of Heterocyclic Compounds p. 1161
Key Ideas in Chapter 24 p. 1162
Additional Problems p. 1163
Pericyclic Reactions p. 1172
Molecular Orbitals of Conjugated [pi]-Electron Systems p. 1175
Electrocyclic Reactions p. 1183
Cycloaddition Reactions p. 1183
Sigmatropic Reactions p. 1192
Summary of the Pericyclic Selection Rules p. 1203
Fluxional Molecules p. 1204
Formation of Vitamin D p. 1205
Key Ideas in Chapter 25 p. 1207
Additional Problems p. 1208
Amino Acids, Peptides, and Proteins p. 1215
Nomenclature of Amino Acids and Peptides p. 1216
Stereochemistry of the [alpha]-Amino Acids p. 1220
Acid-Base Properties of Amino Acids and Peptides p. 1221
Synthesis and Enantiomeric Resolution of [alpha]-Amino Acids p. 1229
Acylation and Esterification Reactions of Amino Acids p. 1232
Determination of Peptide Structure p. 1233
Solid-Phase Peptide Synthesis p. 1246
Combinatorial Chemistry p. 1255
Structures of Peptides and Proteins p. 1261
Enzymes: Biological Catalysts p. 1270
Occurrence of Peptides and Proteins p. 1279
Key Ideas in Chapter 26 p. 1280
Additional Problems p. 1281
Carbohydrates and Nucleic Acids p. 1291
Classification and Properties of Carbohydrates p. 1292
Structures of the Monosaccharides p. 1293
Mutarotation of Carbohydrates p. 1302
Base-Catalyzed Isomerization of Aldoses and Ketoses p. 1306
Glycosides p. 1308
Ether and Ester Derivatives of Carbohydrates p. 1311
Oxidation and Reduction Reactions of Carbohydrates p. 1314
Kiliani-Fischer Synthesis p. 1319
Proof of Glucose Stereochemistry p. 1320
Disaccharides and Polysaccharides p. 1326
Nucleosides, Nucleotides, and Nucleic Acids p. 1333
DNA, RNA, and the Genetic Code p. 1341
Key Ideas in Chapter 27 p. 1345
Additional Problems p. 1346
Appendixes p. 1
Substitutive Nomenclature of Organic Compounds p. 1
Infrared Absorptions of Organic Compounds p. 2
Proton NMR Chemical Shifts in Organic Compounds p. 5
[superscript 13]C NMR Chemical Shifts in Organic Compounds p. 7
Summary of Synthetic Methods p. 8
Reactions Used to Form Carbon-Carbon Bonds p. 13
Typical Acidities and Basicities of Organic Functional Groups p. 14
Credits p. 1
Index p. 1
Organic chemistry
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