Organic Chemistry

Cover......Page 1
Title......Page 2
Copyright......Page 3
Contents......Page 6
Preface......Page 14
Acknowledgments......Page 22
List of How To\'s......Page 24
List of Mechanisms......Page 25
List of Selected Applications......Page 28
What Is Organic Chemistry?......Page 36
Some Representative Organic Molecules......Page 37
Organic Chemistry and Malaria......Page 39
1 Structure and Bonding......Page 42
1.1 The Periodic Table......Page 43
1.2 Bonding......Page 46
1.3 Lewis Structures......Page 48
1.4 Isomers......Page 53
1.6 Resonance......Page 54
1.7 Determining Molecular Shape......Page 60
1.8 Drawing Organic Structures......Page 65
1.9 Hybridization......Page 71
1.10 Ethane, Ethylene, and Acetylene......Page 75
1.11 Bond Length and Bond Strength......Page 80
1.12 Electronegativity and Bond Polarity......Page 82
1.13 Polarity of Molecules......Page 84
1.14 L-Dopa—A Representative Organic Molecule......Page 85
Key Concepts......Page 87
Problems......Page 88
2 Acids and Bases......Page 96
2.1 Brønsted–Lowry Acids and Bases......Page 97
2.2 Reactions of Brønsted–Lowry Acids and Bases......Page 98
2.3 Acid Strength and pK[sub(a)]......Page 101
2.4 Predicting the Outcome of Acid–Base Reactions......Page 103
2.5 Factors That Determine Acid Strength......Page 105
2.6 Common Acids and Bases......Page 113
2.7 Aspirin......Page 115
2.8 Lewis Acids and Bases......Page 116
Key Concepts......Page 119
Problems......Page 120
3 Introduction to Organic Molecules and Functional Groups......Page 126
3.1 Functional Groups......Page 127
3.2 An Overview of Functional Groups......Page 128
3.3 Intermolecular Forces......Page 134
3.4 Physical Properties......Page 138
3.5 Application: Vitamins......Page 144
3.6 Application of Solubility: Soap......Page 146
3.7 Application: The Cell Membrane......Page 148
3.8 Functional Groups and Reactivity......Page 151
3.9 Biomolecules......Page 152
Key Concepts......Page 154
Problems......Page 156
4 Alkanes......Page 163
4.1 Alkanes—An Introduction......Page 164
4.3 An Introduction to Nomenclature......Page 167
4.4 Naming Alkanes......Page 168
4.5 Naming Cycloalkanes......Page 173
4.7 Fossil Fuels......Page 176
4.8 Physical Properties of Alkanes......Page 178
4.9 Conformations of Acyclic Alkanes—Ethane......Page 179
4.10 Conformations of Butane......Page 183
4.11 An Introduction to Cycloalkanes......Page 186
4.12 Cyclohexane......Page 187
4.13 Substituted Cycloalkanes......Page 191
4.14 Oxidation of Alkanes......Page 196
4.15 Lipids—Part 1......Page 199
Key Concepts......Page 201
Problems......Page 202
5 Stereochemistry......Page 209
5.1 Starch and Cellulose......Page 210
5.2 The Two Major Classes of Isomers......Page 212
5.3 Looking Glass Chemistry—Chiral and Achiral Molecules......Page 213
5.4 Stereogenic Centers......Page 216
5.5 Stereogenic Centers in Cyclic Compounds......Page 218
5.6 Labeling Stereogenic Centers with R or S......Page 220
5.7 Diastereomers......Page 225
5.8 Meso Compounds......Page 228
5.9 R and S Assignments in Compounds with Two or More Stereogenic Centers......Page 229
5.10 Disubstituted Cycloalkanes......Page 230
5.11 Isomers—A Summary......Page 231
5.12 Physical Properties of Stereoisomers......Page 232
5.13 Chemical Properties of Enantiomers......Page 237
Key Concepts......Page 239
Problems......Page 240
6 Understanding organic Reactions......Page 248
6.1 Writing Equations for Organic Reactions......Page 249
6.2 Kinds of Organic Reactions......Page 250
6.3 Bond Breaking and Bond Making......Page 252
6.4 Bond Dissociation Energy......Page 256
6.5 Thermodynamics......Page 260
6.6 Enthalpy and Entropy......Page 262
6.7 Energy Diagrams......Page 264
6.8 Energy Diagram for a Two-Step Reaction Mechanism......Page 266
6.9 Kinetics......Page 268
6.10 Catalysts......Page 271
6.11 Enzymes......Page 272
Key Concepts......Page 274
Problems......Page 275
7 Alkyl Halides and Nucleophilic Substitution......Page 282
7.1 Introduction to Alkyl Halides......Page 283
7.2 Nomenclature......Page 284
7.3 Physical Properties......Page 285
7.4 Interesting Alkyl Halides......Page 286
7.5 The Polar Carbon–Halogen Bond......Page 287
7.6 General Features of Nucleophilic Substitution......Page 288
7.7 The Leaving Group......Page 290
7.8 The Nucleophile......Page 292
7.9 Possible Mechanisms for Nucleophilic Substitution......Page 296
7.10 Two Mechanisms for Nucleophilic Substitution......Page 297
7.11 The S[sub(N)]2 Mechanism......Page 298
7.12 The S[sub(N)]1 Mechanism......Page 304
7.13 Carbocation Stability......Page 308
7.14 The Hammond Postulate......Page 310
7.15 When Is the Mechanism S[sub(N)]1 or S[sub(N)]2?......Page 313
7.16 Biological Nucleophilic Substitution......Page 318
7.18 Organic Synthesis......Page 321
Key Concepts......Page 323
Problems......Page 325
8 Alkyl Halides and Elimination Reactions......Page 332
8.1 General Features of Elimination......Page 333
8.2 Alkenes—The Products of Elimination Reactions......Page 334
8.4 The E2 Mechanism......Page 338
8.5 The Zaitsev Rule......Page 343
8.6 The E1 Mechanism......Page 345
8.7 S[sub(N)]1 and E1 Reactions......Page 348
8.8 Stereochemistry of the E2 Reaction......Page 349
8.9 When Is the Mechanism E1 or E2?......Page 352
8.10 E2 Reactions and Alkyne Synthesis......Page 353
8.11 When Is the Reaction S[sub(N)]1, S[sub(N)]2, E1, or E2?......Page 354
Key Concepts......Page 358
Problems......Page 360
9 Alcohols, Ethers, and Related Compounds......Page 366
9.1 Introduction......Page 367
9.2 Structure and Bonding......Page 368
9.3 Nomenclature......Page 369
9.4 Physical Properties......Page 372
9.5 Interesting Alcohols, Ethers, and Epoxides......Page 373
9.6 Preparation of Alcohols, Ethers, and Epoxides......Page 376
9.7 General Features—Reactions of Alcohols, Ethers, and Epoxides......Page 378
9.8 Dehydration of Alcohols to Alkenes......Page 380
9.9 Carbocation Rearrangements......Page 383
9.10 Dehydration Using POCl[sub(3)] and Pyridine......Page 386
9.11 Conversion of Alcohols to Alkyl Halides with HX......Page 387
9.12 Conversion of Alcohols to Alkyl Halides with SOCl[sub(2)] and PBr[sub(3)]......Page 391
9.13 Tosylate—Another Good Leaving Group......Page 394
9.14 Reaction of Ethers with Strong Acid......Page 397
9.15 Thiols and Sulfides......Page 399
9.16 Reactions of Epoxides......Page 402
9.17 Application: Epoxides, Leukotrienes, and Asthma......Page 406
Key Concepts......Page 408
Problems......Page 411
10 Alkenes......Page 418
10.1 Introduction......Page 419
10.2 Calculating Degrees of Unsaturation......Page 420
10.3 Nomenclature......Page 422
10.5 Interesting Alkenes......Page 426
10.6 Lipids—Part 2......Page 428
10.7 Preparation of Alkenes......Page 430
10.8 Introduction to Addition Reactions......Page 431
10.9 Hydrohalogenation—Electrophilic Addition of HX......Page 432
10.10 Markovnikov\'s Rule......Page 435
10.11 Stereochemistry of Electrophilic Addition of HX......Page 437
10.12 Hydration—Electrophilic Addition of Water......Page 439
10.13 Halogenation—Addition of Halogen......Page 440
10.14 Stereochemistry of Halogenation......Page 441
10.15 Halohydrin Formation......Page 443
10.16 Hydroboration–Oxidation......Page 446
10.17 Keeping Track of Reactions......Page 450
10.18 Alkenes in Organic Synthesis......Page 452
Key Concepts......Page 453
Problems......Page 454
11 Alkynes......Page 461
11.1 Introduction......Page 462
11.2 Nomenclature......Page 463
11.3 Physical Properties......Page 464
11.4 Interesting Alkynes......Page 465
11.5 Preparation of Alkynes......Page 466
11.6 Introduction to Alkyne Reactions......Page 467
11.7 Addition of Hydrogen Halides......Page 469
11.8 Addition of Halogen......Page 471
11.9 Addition of Water......Page 472
11.10 Hydroboration–Oxidation......Page 474
11.11 Reaction of Acetylide Anions......Page 476
11.12 Synthesis......Page 479
Key Concepts......Page 482
Problems......Page 483
12 Oxidation and Reduction......Page 490
12.1 Introduction......Page 491
12.2 Reducing Agents......Page 492
12.3 Reduction of Alkenes......Page 493
12.4 Application: Hydrogenation of Oils......Page 496
12.5 Reduction of Alkynes......Page 498
12.6 The Reduction of Polar C–X σ Bonds......Page 501
12.7 Oxidizing Agents......Page 502
12.8 Epoxidation......Page 504
12.9 Dihydroxylation......Page 507
12.10 Oxidative Cleavage of Alkenes......Page 509
12.12 Oxidation of Alcohols......Page 511
12.13 Green Chemistry......Page 514
12.14 Biological Oxidation......Page 516
12.15 Sharpless Epoxidation......Page 517
Key Concepts......Page 520
Problems......Page 522
13 Mass Spectrometry and Infrared Spectroscopy......Page 530
13.1 Mass Spectrometry......Page 531
13.2 Alkyl Halides and the M + 2 Peak......Page 535
13.3 Fragmentation......Page 536
13.4 Other Types of Mass Spectrometry......Page 539
13.5 Electromagnetic Radiation......Page 541
13.6 Infrared Spectroscopy......Page 543
13.7 IR Absorptions......Page 545
13.8 IR and Structure Determination......Page 552
Key Concepts......Page 554
Problems......Page 555
14 Nuclear Magnetic Resonance Spectroscopy......Page 562
14.1 An Introduction to NMR Spectroscopy......Page 563
14.2 [sup(1)]H NMR: Number of Signals......Page 566
14.3 [sup(1)]H NMR: Position of Signals......Page 570
14.4 The Chemical Shift of Protons on sp[sup(2)] and sp Hybridized Carbons......Page 574
14.5 [sup(1)]H NMR: Intensity of Signals......Page 576
14.6 [sup(1)]H NMR: Spin–Spin Splitting......Page 577
14.7 More Complex Examples of Splitting......Page 581
14.8 Spin–Spin Splitting in Alkenes......Page 584
14.9 Other Facts About [sup(1)]H NMR Spectroscopy......Page 586
14.10 Using [sup(1)]H NMR to Identify an Unknown......Page 589
14.11 [sup(13)]C NMR Spectroscopy......Page 591
Problems......Page 596
15 Radical Reactions......Page 605
15.1 Introduction......Page 606
15.2 General Features of Radical Reactions......Page 607
15.3 Halogenation of Alkanes......Page 609
15.4 The Mechanism of Halogenation......Page 610
15.6 Chlorination Versus Bromination......Page 613
15.7 Halogenation as a Tool in Organic Synthesis......Page 616
15.8 The Stereochemistry of Halogenation Reactions......Page 617
15.9 Application: The Ozone Layer and CFCs......Page 619
15.10 Radical Halogenation at an Allylic Carbon......Page 620
15.11 Application: Oxidation of Unsaturated Lipids......Page 623
15.12 Application: Antioxidants......Page 624
15.13 Radical Addition Reactions to Double Bonds......Page 625
15.14 Polymers and Polymerization......Page 628
Key Concepts......Page 630
Problems......Page 631
16 Conjugation, Resonance, and Dienes......Page 639
16.1 Conjugation......Page 640
16.2 Resonance and Allylic Carbocations......Page 642
16.3 Common Examples of Resonance......Page 643
16.4 The Resonance Hybrid......Page 645
16.5 Electron Delocalization, Hybridization, and Geometry......Page 647
16.6 Conjugated Dienes......Page 648
16.8 The Carbon–Carbon s Bond Length in Buta-1,3-diene......Page 649
16.9 Stability of Conjugated Dienes......Page 650
16.10 Electrophilic Addition: 1,2-Versus 1,4-Addition......Page 651
16.11 Kinetic Versus Thermodynamic Products......Page 653
16.12 The Diels–Alder Reaction......Page 656
16.13 Specific Rules Governing the Diels–Alder Reaction......Page 658
16.14 Other Facts About the Diels–Alder Reaction......Page 662
16.15 Conjugated Dienes and Ultraviolet Light......Page 665
Key Concepts......Page 667
Problems......Page 669
17 Benzene and Aromatic Compounds......Page 676
17.1 Background......Page 677
17.2 The Structure of Benzene......Page 678
17.3 Nomenclature of Benzene Derivatives......Page 679
17.4 Spectroscopic Properties......Page 682
17.5 Interesting Aromatic Compounds......Page 683
17.6 Benzene\'s Unusual Stability......Page 684
17.7 The Criteria for Aromaticity—Hückel\'s Rule......Page 686
17.8 Examples of Aromatic Compounds......Page 689
17.9 What Is the Basis of Hückel\'s Rule?......Page 695
17.10 The Inscribed Polygon Method for Predicting Aromaticity......Page 698
17.11 Buckminsterfullerene—Is It Aromatic?......Page 701
Key Concepts......Page 702
Problems......Page 703
18 Reactions of Aromatic Compounds......Page 712
18.1 Electrophilic Aromatic Substitution......Page 713
18.2 The General Mechanism......Page 714
18.3 Halogenation......Page 716
18.4 Nitration and Sulfonation......Page 717
18.5 Friedel–Crafts Alkylation and Friedel–Crafts Acylation......Page 719
18.6 Substituted Benzenes......Page 726
18.7 Electrophilic Aromatic Substitution of Substituted Benzenes......Page 729
18.8 Why Substituents Activate or Deactivate a Benzene Ring......Page 731
18.9 Orientation Effects in Substituted Benzenes......Page 733
18.10 Limitations on Electrophilic Substitution Reactions with Substituted Benzenes......Page 736
18.11 Disubstituted Benzenes......Page 738
18.12 Synthesis of Benzene Derivatives......Page 740
18.13 Nucleophilic Aromatic Substitution......Page 741
18.14 Halogenation of Alkyl Benzenes......Page 744
18.15 Oxidation and Reduction of Substituted Benzenes......Page 746
18.16 Multistep Synthesis......Page 750
Key Concepts......Page 753
Problems......Page 756
19 Carboxylic Acids and the Acidity of the O–H Bond......Page 764
19.1 Structure and Bonding......Page 765
19.2 Nomenclature......Page 766
19.3 Physical Properties......Page 769
19.4 Spectroscopic Properties......Page 770
19.5 Interesting Carboxylic Acids......Page 771
19.6 Aspirin, Arachidonic Acid, and Prostaglandins......Page 772
19.7 Preparation of Carboxylic Acids......Page 774
19.8 Reactions of Carboxylic Acids—General Features......Page 775
19.9 Carboxylic Acids—Strong Organic Brønsted–Lowry Acids......Page 776
19.10 Inductive Effects in Aliphatic Carboxylic Acids......Page 779
19.11 Substituted Benzoic Acids......Page 781
19.12 Extraction......Page 784
19.13 Sulfonic Acids......Page 786
19.14 Amino Acids......Page 787
Key Concepts......Page 790
Problems......Page 791
20 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction......Page 799
20.1 Introduction......Page 800
20.2 General Reactions of Carbonyl Compounds......Page 801
20.3 A Preview of Oxidation and Reduction......Page 804
20.4 Reduction of Aldehydes and Ketones......Page 806
20.5 The Stereochemistry of Carbonyl Reduction......Page 808
20.6 Enantioselective Carbonyl Reductions......Page 809
20.7 Reduction of Carboxylic Acids and Their Derivatives......Page 812
20.9 Organometallic Reagents......Page 817
20.10 Reaction of Organometallic Reagents with Aldehydes and Ketones......Page 821
20.11 Retrosynthetic Analysis of Grignard Products......Page 825
20.12 Protecting Groups......Page 827
20.13 Reaction of Organometallic Reagents with Carboxylic Acid Derivatives......Page 829
20.14 Reaction of Organometallic Reagents with Other Compounds......Page 832
20.15 α,β-Unsaturated Carbonyl Compounds......Page 834
20.17 Synthesis......Page 837
Key Concepts......Page 840
Problems......Page 843
21 Aldehydes and Ketones—Nucleophilic Addition......Page 852
21.1 Introduction......Page 853
21.2 Nomenclature......Page 854
21.3 Physical Properties......Page 857
21.4 Spectroscopic Properties......Page 858
21.5 Interesting Aldehydes and Ketones......Page 860
21.6 Preparation of Aldehydes and Ketones......Page 861
21.7 Reactions of Aldehydes and Ketones—General Considerations......Page 863
21.8 Nucleophilic Addition of H[sup(–)] and R[sup(–)]—A Review......Page 866
21.9 Nucleophilic Addition of [sup(–)]CN......Page 868
21.10 The Wittig Reaction......Page 870
21.11 Addition of 1° Amines......Page 875
21.12 Addition of 2° Amines......Page 877
21.13 Addition of H[sub(2)]O—Hydration......Page 879
21.14 Addition of Alcohols—Acetal Formation......Page 882
21.15 Acetals as Protecting Groups......Page 886
21.16 Cyclic Hemiacetals......Page 887
21.17 An Introduction to Carbohydrates......Page 890
Key Concepts......Page 891
Problems......Page 893
22 Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution......Page 903
22.1 Introduction......Page 904
22.2 Structure and Bonding......Page 906
22.3 Nomenclature......Page 908
22.4 Physical Properties......Page 912
22.5 Spectroscopic Properties......Page 913
22.6 Interesting Esters and Amides......Page 915
22.7 Introduction to Nucleophilic Acyl Substitution......Page 917
22.8 Reactions of Acid Chlorides......Page 920
22.9 Reactions of Anhydrides......Page 922
22.10 Reactions of Carboxylic Acids......Page 924
22.11 Reactions of Esters......Page 929
22.12 Application: Lipid Hydrolysis......Page 931
22.13 Reactions of Amides......Page 934
22.14 Application: The Mechanism of Actionof β-Lactam Antibiotics......Page 935
22.15 Summary of Nucleophilic Acyl Substitution Reactions......Page 936
22.16 Natural and Synthetic Fibers......Page 937
22.17 Biological Acylation Reactions......Page 939
22.18 Nitriles......Page 941
Key Concepts......Page 946
Problems......Page 949
23 Substitution Reactionsof Carbonyl Compoundsat the α Carbon......Page 959
23.1 Introduction......Page 960
23.2 Enols......Page 961
23.3 Enolates......Page 963
23.4 Enolates of Unsymmetrical Carbonyl Compounds......Page 969
23.5 Racemization at the α Carbon......Page 971
23.7 Halogenation at the a α Carbon......Page 972
23.8 Direct Enolate Alkylation......Page 977
23.9 Malonic Ester Synthesis......Page 980
23.10 Acetoacetic Ester Synthesis......Page 984
Key Concepts......Page 987
Problems......Page 988
24 Carbonyl Condensation Reactions......Page 997
24.1 The Aldol Reaction......Page 998
24.2 Crossed Aldol Reactions......Page 1002
24.3 Directed Aldol Reactions......Page 1006
24.4 Intramolecular Aldol Reactions......Page 1008
24.5 The Claisen Reaction......Page 1010
24.6 The Crossed Claisen and Related Reactions......Page 1012
24.7 The Dieckmann Reaction......Page 1014
24.8 The Michael Reaction......Page 1015
24.9 The Robinson Annulation......Page 1017
Key Concepts......Page 1021
Problems......Page 1022
25 Amines......Page 1031
25.2 Structure and Bonding......Page 1032
25.3 Nomenclature......Page 1034
25.4 Physical Properties......Page 1036
25.5 Spectroscopic Properties......Page 1037
25.6 Interesting and Useful Amines......Page 1039
25.7 Preparation of Amines......Page 1042
25.9 Amines as Bases......Page 1049
25.10 Relative Basicity of Amines and Other Compounds......Page 1051
25.11 Amines as Nucleophiles......Page 1057
25.12 Hofmann Elimination......Page 1059
25.13 Reaction of Amines with Nitrous Acid......Page 1062
25.14 Substitution Reactions of Aryl Diazonium Salts......Page 1064
25.15 Coupling Reactions of Aryl Diazonium Salts......Page 1069
25.16 Application: Synthetic Dyes and Sulfa Drugs......Page 1071
Key Concepts......Page 1073
Problems......Page 1076
26 Carbon–Carbon Bond-Forming Reactions in Organic Synthesis......Page 1084
26.1 Coupling Reactions of Organ ocuprate Reagents......Page 1085
26.2 Suzuki Reaction......Page 1087
26.3 Heck Reaction......Page 1091
26.4 Carbenes and Cyclopropane Synthesis......Page 1093
26.5 Simmons–Smith Reaction......Page 1096
26.6 Metathesis......Page 1097
Key Concepts......Page 1102
Problems......Page 1103
27 Pericyclic Reactions......Page 1111
27.1 Types of Pericyclic Reactions......Page 1112
27.2 Molecular Orbitals......Page 1113
27.3 Electrocyclic Reactions......Page 1116
27.4 Cycloaddition Reactions......Page 1122
27.5 Sigmatropic Rearrangements......Page 1126
27.6 Summary of Rules for Pericyclic Reactions......Page 1132
Key Concepts......Page 1133
Problems......Page 1134
28 Carbohydrates......Page 1141
28.1 Introduction......Page 1142
28.2 Monosaccharides......Page 1143
28.3 The Family of D-Aldoses......Page 1148
28.4 The Family of D-Ketoses......Page 1150
28.6 The Cyclic Forms of Monosaccharides......Page 1151
28.7 Glycosides......Page 1159
28.8 Reactions of Monosaccharides at the OH Groups......Page 1162
28.9 Reactions at the Carbonyl Group—Oxidation and Reduction......Page 1163
28.10 Reactions at the Carbonyl Group—Adding or Removing One Carbon Atom......Page 1166
28.11 Disaccharides......Page 1169
28.12 Polysaccharides......Page 1173
28.13 Other Important Sugars and Their Derivatives......Page 1175
Key Concepts......Page 1179
Problems......Page 1182
29 Amino Acids and Proteins......Page 1187
29.1 Amino Acids......Page 1188
29.2 Synthesis of Amino Acids......Page 1191
29.3 Separation of Amino Acids......Page 1194
29.4 Enantioselective Synthesis of Amino Acids......Page 1198
29.5 Peptides......Page 1199
29.6 Peptide Sequencing......Page 1204
29.7 Peptide Synthesis......Page 1207
29.8 Automated Peptide Synthesis......Page 1212
29.9 Protein Structure......Page 1214
29.10 Important Proteins......Page 1221
Key Concepts......Page 1224
Problems......Page 1226
30 Synthetic Polymers......Page 1233
30.1 Introduction......Page 1234
30.2 Chain-Growth Polymers—Addition Polymers......Page 1235
30.3 Anionic Polymerization of Epoxides......Page 1242
30.4 Ziegler–Natta Catalysts and Polymer Stereochemistry......Page 1243
30.5 Natural and Synthetic Rubbers......Page 1245
30.6 Step-Growth Polymers—Condensation Polymers......Page 1246
30.7 Polymer Structure and Properties......Page 1251
30.8 Green Polymer Synthesis......Page 1252
30.9 Polymer Recycling and Disposal......Page 1255
Key Concepts......Page 1258
Problems......Page 1260
31 Lipids......Page 1266
31.1 Introduction......Page 1267
31.2 Waxes......Page 1268
31.3 Triacylglycerols......Page 1269
31.4 Phospholipids......Page 1273
31.5 Fat-Soluble Vitamins......Page 1276
31.6 Eicosanoids......Page 1277
31.7 Terpenes......Page 1280
31.8 Steroids......Page 1285
Key Concepts......Page 1290
Problems......Page 1291
Appendix A: pK[sub(a)] Values for Selected Compounds......Page 1296
Appendix B: Nomenclature......Page 1298
Appendix C: Bond Dissociation Energies for Some Common Bonds [A–B → A• + •B]......Page 1302
Appendix D: Reactions That Form Carbon–Carbon Bond......Page 1303
Appendix E: Characteristic IR Absorption Frequencies......Page 1304
Appendix F: Characteristic NMR Absorptions......Page 1305
Appendix G: General Types of Organic Reactions......Page 1307
Appendix H: How to Synthesize Particular Functional Groups......Page 1309
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