Organic Chemistry

Description

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 A ......Page 1314 C ......Page 1316 D ......Page 1318 E ......Page 1319 G......Page 1321 H ......Page 1322 K ......Page 1323 M ......Page 1324 N ......Page 1325 P ......Page 1326 R ......Page 1328 S ......Page 1329 T ......Page 1330 U ......Page 1331 Z ......Page 1332 Credits......Page 1334 A ......Page 1336 B ......Page 1341 C ......Page 1343 D ......Page 1347 E ......Page 1348 F ......Page 1351 H ......Page 1352 I ......Page 1354 L ......Page 1355 M ......Page 1356 N ......Page 1358 O ......Page 1359 P ......Page 1360 R ......Page 1363 S ......Page 1364 T ......Page 1367 V ......Page 1368 Z ......Page 1369