Advanced organic chemistry

Cover......Page 1
Half Title Page......Page 2
Copyright......Page 3
CONTENTS......Page 4
PREFACE......Page 10
Acknowledgments......Page 14
 1.1 Organic Structure: A Brief History......Page 16
  Lewis Structures......Page 17
  Representing Organic Compounds: Structural Formulas......Page 19
  Arrhenius Acids and Bases......Page 22
  Lowry-Brønsted Acids and Bases......Page 23
  Leveling Effect......Page 27
  Writing Mechanisms......Page 28
  Homolysis......Page 29
  Heterolysis......Page 30
  Kinetic Order, Molecularity, and Mechanistic Type......Page 33
 1.4 Resonance......Page 39
 1.5 Spectroscopy and Chromatography......Page 45
 Chapter Summary......Page 46
 Key Terms......Page 47
 Additional Problems......Page 48
  Representing Stereochemistry......Page 52
  Symmetry Elements in Organic Compounds......Page 54
  Protocenters of Stereochemistry......Page 57
 2.2 Absolute Configuration......Page 61
  Planar Chirality......Page 64
  Diastereoisomers......Page 65
  Epimers......Page 67
  Stereotopism......Page 68
  Geometric Isomers......Page 69
  Stereochemistry in Reactions: Defining Terms......Page 71
 2.3 Optical Purity and Configuration......Page 72
  Exciton Chirality and Absolute Configuration......Page 76
 2.4 Conformation......Page 78
  Creating New Chiral Centers in a Reaction......Page 82
  Using Conformational Analysis in Synthesis......Page 90
 2.6 How Well Did It Go? Measuring Enantiomer Ratios......Page 92
 2.7 Chirality at Atoms Other Than Carbon: Inversion of Pyramidal Centers......Page 93
 Chapter Summary......Page 95
 Additional Problems......Page 96
 3.2 Name Reactions: A Historical Overview......Page 102
 3.3 Acronyms and Abbreviations......Page 106
 4.1 Introduction......Page 120
 4.2 Atomic Orbitals: The History of the Modern Atomic Model......Page 121
  Standing Waves and Atomic Orbitals......Page 122
 4.3 Covalent Bonding and Molecular Orbitals......Page 126
  Hybrid Atomic Orbitals: Valence Bond Theory......Page 128
  The t Bond Model of Multiple Bonds: Variable Hybridization......Page 134
  Extended p Systems: Delocalized p Orbitals of Aliphatic Compounds......Page 135
  Benzene and Aromaticity......Page 139
 Chapter Summary......Page 140
 Additional Problems......Page 141
 5.1 Chemical Reactions: Frontier Orbitals......Page 144
  Conformational and Stereoelectronic Effects......Page 150
 5.2 Using Frontier Molecular Orbitals to Categorize Reactions and Reagents......Page 152
  Perturbation Approximations for Orbital Coefficients......Page 154
  Frontier Molecular Orbital Overlap Between n and a Orbitals......Page 157
  Frontier Molecular Orbital Overlap Between n and p * Orbitals......Page 161
  Frontier Molecular Orbital Overlap Between n and s * Orbitals......Page 162
  Frontier Molecular Orbital Overlap Between p and a Orbitals......Page 163
  Frontier Molecular Orbital Overlap Between p and p* Orbitals......Page 164
  Frontier Molecular Orbital Overlap Between p and s* Orbitals......Page 167
  Frontier Molecular Orbital Overlap Between a and s Orbitals......Page 168
  Frontier Molecular Orbital Overlap Between s and p* Orbitals......Page 169
  Frontier Molecular Orbital Overlap Between s and s* Orbitals......Page 170
  The Anomeric Effect......Page 171
  Nucleophilic Cyclizations—Baldwin’s Rules......Page 172
 5.5 Radical Reactions......Page 174
 Key Terms......Page 175
 Additional Problems......Page 176
  Definitions......Page 178
  Orbital Symmetry......Page 180
  Electrocyclizations......Page 182
  Cycloadditions......Page 183
 6.4 Sigmatropic Rearrangements: More Details......Page 185
  [1,n]-Sigmatropic Rearrangements of Hydrogen......Page 186
  [1,n]-Sigmatropic Rearrangements of Alkyl......Page 187
  [3,3]-Sigmatropic Rearrangements......Page 188
  Categorization of Cycloadditions......Page 195
  Qualitative Perturbation Theory: Approximating Frontier Orbitals of Substituted Alkenes and Dienes......Page 198
  Predicting Regiochemistry......Page 200
  Intramolecular Diels-Alder reactions......Page 201
  Carbene Additions: [2 + 1] Cycloadditions......Page 203
  Ketene Additions: [2 + 2 ] Cycloadditions......Page 205
  1,3-Dipolar Additions......Page 211
  Generation of 1,3-Dipoles......Page 213
  1,3-Dipolar Cycloadditions and “Click Chemistry”......Page 214
 6.6 Ene, Retro-Ene, and Similar Reactions......Page 216
  Cyclic Eliminations Through Six-Membered Transition States......Page 217
  Cyclic Eliminations Through Five-Membered Transition States......Page 219
  Electrocyclization......Page 221
  Cycloadditions......Page 222
  Another Look at Electrocyclizations......Page 224
  Coupling Pericyclic Reactions: Tandem and Domino Reactions......Page 227
 Chapter Summary......Page 229
 Additional Problems......Page 230
 7.1 Benzene: The Beginning......Page 236
 7.2 Aromaticity and Antiaromaticity: The Hückel Molecular Orbital Model of Cyclic Polyenes......Page 237
  Heterocyclic Compounds: Aromatic or Not? Where is the Lone Pair?......Page 243
  Orbital Energies of Hückel p Orbitals of Cyclic Systems......Page 245
  Hückel Molecular Orbitals in Benzene and Aromatic Compounds......Page 246
  Thermodynamics and Aromatic Resonance Stabilization Energy......Page 248
  Structural Evidence of Aromaticity......Page 251
  Magnetic Evidence of Aromaticity......Page 252
  Computational Evaluation of Aromaticity......Page 254
 7.4 Möbius Aromaticity......Page 258
 7.5 Homoaromaticity......Page 261
  Aromatic Transition States......Page 264
 7.6 The Rest of the Story: The History and Mythology of Benzene......Page 265
 Additional Problems......Page 269
 8.1 Introduction......Page 274
 8.2 Solvents and Solubility......Page 277
  Ionic Liquids......Page 283
 8.3 Reaction Kinetics......Page 285
  Second-Order Reactions......Page 286
  Making Deductions from the Rate Law......Page 287
  Preequilibrium and Catalysis......Page 289
  Deducing a Rate Law from a Reaction Coordinate Diagram......Page 290
  Predicting a Rate Law from a Mechanism......Page 291
 8.4 Activation Parameters from Kinetic Studies......Page 294
 8.5 Correlating Reaction Rates: Linear Free Energy Relationships......Page 295
  Substituent Effects: the Hammett Equation......Page 297
  Solvent Effects......Page 302
  The Salt Effect......Page 304
  The Brønsted Catalysis Law......Page 305
 8.6 Isotope and Element Effects......Page 306
  Isotope Effects......Page 307
  Using Element and Isotope Effects to Postulate Mechanism and Transition State Structures......Page 311
 8.7 Trapping and Crossover Experiments......Page 314
 8.8 The Variable Transition State and the Concept of the Mechanistic Spectrum......Page 316
 8.9 Using Regiochemistry and Stereochemistry......Page 322
 8.10 The Reactivity-Selectivity Principle......Page 323
 Additional Problems......Page 324
 9.1 Carbocations......Page 332
  Hyperconjugation......Page 335
  Comparison of Conjugation and Hyperconjugation......Page 336
  Aromatic and Homoaromatic Carbocations......Page 337
  Structure of Carbocations......Page 339
  Spectroscopy of Carbocations......Page 340
 9.2 Rearrangements......Page 342
  Transannular Rearrangements......Page 346
 9.3 Neighboring Group Participation......Page 347
 9.4 Nonclassical Carbocations......Page 350
 9.5 Methods for Generating Carbocations......Page 354
 Chapter Summary......Page 357
 Additional Problems......Page 358
 10.1 Introduction......Page 362
  The Electrophile: Generating Carbocation Electrophiles......Page 363
  The Electrophile: Strength and Reactivity......Page 365
  The Arene: Reactivity and Orientation......Page 367
  Acylation......Page 370
  Asymmetric Friedel-Crafts Alkylation......Page 372
  The Role of Solvent......Page 375
  Houben-Hoesch Acylation......Page 376
 10.3 Formylation......Page 379
  Gattermann, Gattermann-Koch, and Gattermann-Olah Formylations......Page 380
  Vilsmeier-Haack Formylation......Page 381
  Duff Formylation Reaction......Page 382
 10.4 Addition of Stabilized Carbocations: The Prins, Mannich, and Mukaiyama Reactions......Page 385
  The Prins Reaction......Page 386
  Mannich Reaction: An Iminium Equivalent of the Aldol Addition......Page 391
  Electron-Rich Alkenes: Surrogates of Enolate Anions for Reactions with Carbocations......Page 395
 Key Terms......Page 401
 Additional Problems......Page 402
 11.1 Carbanions: Introduction and Overview......Page 406
  Stabilization of Carbanions: Comparison and Contrast with Cations......Page 409
  Direct Synthesis......Page 412
  Metathesis Between Alkyl Halides and Metal Alkyls......Page 413
  Metathesis Between Metal Halides and Metal Alkyls......Page 414
  Metathesis Between Metal Alkyls......Page 415
  Metalation of Hydrocarbons......Page 416
  Effects of Overall Charge on Nucleophilicity......Page 418
  Acid-Base Chemistry of Metal Alkyls—A Limitation on Their Use......Page 422
  Some Final Words on the Reactivity of Simple Metal Alkyls......Page 423
 11.3 Carbanions Stabilized by Heteroatoms......Page 426
  Ylides......Page 428
  Alkylsulfinyl Anions, Phosphonate Anions, and Anions from Phosphine Oxides......Page 431
  Silane Anions: The Peterson Olefination......Page 433
  Structure and Bonding in Enolate Anions and Nitrile a-Anions......Page 435
  Controlling Regiochemistry During Formation of Ketone Enolates......Page 437
  Deprotonation of Conjugated Systems......Page 439
  Deuterium Exchange and Epimerization......Page 441
 11.5 Rearrangements of Carbanions......Page 445
 Additional Problems......Page 449
 12.2 Substitution and Addition with Metal Alkyl Reagents Having C—M ?? Bonds......Page 454
  Using Metal Alkyls as Bases......Page 457
  Alkylation with Metal Alkyls......Page 458
  Enolate Regiochemistry......Page 473
  Enolate Stereochemistry......Page 474
  Alkylation of Enolates......Page 476
 12.4 The Aldol Addition Reaction......Page 481
  Stereochemistry in the Aldol Addition......Page 482
  Asymmetric Aldol Additions......Page 488
  Organocatalysis in Enolate Additions......Page 492
  Michael Addition of Enolate Anions......Page 496
  Metalated Imines and Hydrazones......Page 501
  Enamines......Page 505
 Chapter Summary......Page 507
 Additional Problems......Page 508
 13.1 Free Radicals......Page 512
  Structure and Bonding in Free Radicals......Page 514
  Reactivity of Free Radicals......Page 515
  Propagation......Page 516
  Initiation......Page 517
  Radicals in Synthesis......Page 518
 13.2 Carbenes......Page 520
  Carbenoids......Page 522
  Carbene Addition......Page 523
  Carbenes and Carbenoids in Synthesis......Page 524
  Rearrangements in Carbenes......Page 526
  Stable Carbenes......Page 527
 13.3 Nitrenes......Page 531
 13.4 Arynes......Page 533
  Structure and Bonding in Benzyne......Page 535
  Reactivity of Benzyne......Page 536
  p-Benzyne and m-Benzyne......Page 538
 Additional Problems......Page 543
  Simple Homolysis of Nonradical Precursors......Page 548
  Reduction Reactions to Generate Free Radicals......Page 552
  Oxidation Reactions to Generate Free Radicals......Page 554
  Photochemical Generation of Radicals: Ketone Photolysis......Page 555
  Fragmentation......Page 557
  Atom Abstraction (Atom Transfer)......Page 558
  Addition......Page 561
 14.3 Reactions of Free Radicals Useful for Synthesis......Page 563
  Radical Decarboxylations: Substitution of a Carboxyl Group......Page 564
  Intramolecular Hydrogen Atom Transfer......Page 565
 14.4 Additions and Cyclizations of Free Radicals......Page 572
  Addition to Carbene-and Nitrene-like Compounds......Page 578
  Group Transfer Reactions and the Persistent Radical Effect......Page 580
  Ketone Photolysis......Page 582
  Bergman Cycloaromatization......Page 583
 Chapter Summary......Page 584
 Additional Problems......Page 585
 15.1 What Is Organic Synthesis?......Page 592
  Elegance or, “What Constitutes a Good Organic Synthesis?”......Page 594
  Molecular Complexity......Page 595
 15.2 Organic Reactions: Tools of the Synthetic Chemist......Page 598
  Historical Development of Organic Synthesis......Page 599
  Retrosynthetic Analysis......Page 606
  Other Retrosynthetic Strategies......Page 617
 15.4 Applying Retrosynthetic Analysis to a Real Example......Page 620
  Chemoselectivity......Page 625
  Regioselectivity......Page 626
  Stereoselectivity......Page 627
  Esters......Page 629
  Ethers......Page 630
  Acetals and Ketals......Page 631
  1,2- and 1,3-Diols......Page 632
  Wiesner’s Synthesis of (±)-13-Desoxydelphonine: A Case Study Before the Widespread Use of Silyl Groups......Page 633
  Silyl Ethers......Page 635
  Protection of Aldehydes and Ketones......Page 639
  Carboxylic Acids......Page 645
 15.8 Protection of Amines......Page 646
  Alkenes......Page 650
  Alkynes......Page 651
 Key Terms......Page 653
 Additional Problems......Page 654
 16.2 The Aldol Condensation and Related Reactions......Page 662
  The Knoevenagel Condensation......Page 663
  Intramolecular Aldol Condensations via Enamines......Page 664
 16.3 Condensations Where the Initial Adduct Is Intercepted......Page 665
  The Darzens Condensation......Page 666
  The Corey-Chaykovsky Reaction......Page 667
  The Stobbe Condensation......Page 668
  The Claisen Condensation......Page 671
  The Dieckmann Condensation......Page 672
  Decarboxylation of ß-Ketoacids......Page 673
 16.5 The Wittig, Horner-Wadsworth-Emmons, and Related Reactions......Page 676
  The Schlosser Modification......Page 679
  The Horner-Wadsworth-Emmons Reaction......Page 681
  Phosphorus-based Condensation Reactions to Give Alkynes......Page 682
  Silicon-based Olefination: The Peterson Reaction......Page 686
  Sulfur-based Olefination......Page 687
  Transition Metal-based Reagents for Olefination......Page 689
 16.6 Cascade Reactions Initiated by Carbon Nucleophiles......Page 692
  Michael-Initiated Ring Closure......Page 693
  The Morita-Baylis-Hillman and Benzoin Condensation Reactions......Page 694
 Key Terms......Page 697
 Additional Problems......Page 698
 17.1 Catalysis and “Green” Chemistry......Page 704
 17.2 Bonding in Organometallic Complexes......Page 705
  Electron Bookkeeping and the “18-Electron Rule”......Page 708
  Carbon-Metal Bonding in Organotransition Metal Complexes......Page 710
  Ligand Substitution......Page 712
  Oxidative Addition and Reductive Elimination......Page 713
  Insertion Reactions......Page 714
  ß-Hydride Elimination......Page 715
  Transmetallation and Exchange with Metalloids......Page 716
  Synthetic Reactions Involving Nucleophilic Attack on Ligands......Page 719
  Synthetic Reactions Involving Electrophilic Attack on Ligands......Page 722
  Oligomerization of Alkene and Alkyne .² Ligands......Page 723
  Metathesis and Metallocycle Formation......Page 726
 17.5 Hydrometallation: Making the Organometallic Reagents by Addition......Page 731
  Hydroboration......Page 732
  Hydroalumination......Page 737
  Hydrozirconation......Page 739
  Hydrostannylation and Hydrosilation......Page 740
  Carbometallation......Page 742
  Why Are These Hydrometallation Reactions Important?......Page 743
 17.6 Palladium-Catalyzed Substitution: Tsuji-Trost and Buchwald-Hartwig Reactions......Page 745
  The Buchwald-Hartwig and Related Cross-Coupling Reactions......Page 749
 17.7 Cross-Coupling Reactions to Form C—C Bonds......Page 752
  The Heck Coupling Reaction......Page 753
  The Stille, Negishi, Hiyama, and Kumada Coupling Reactions......Page 756
  The Suzuki-Miyaura and Related Coupling Reactions......Page 762
 Chapter Summary......Page 767
 Additional Problems......Page 768
  Oxidation Numbers: Use and Limitations......Page 776
  Oxidizable and Reducible Groups in Organic Compounds......Page 778
 18.2 Overview of Oxidation......Page 780
 18.3 Oxidation of Alcohols to Aldehydes and Ketones with Stoichiometric Metal-Based Reagents......Page 781
  Metal-Based Reagents......Page 782
  Other Transition Metal-Based Oxidants......Page 786
  Oxidation of Tertiary Allylic Alcohols to Ketones: Transposition of the Carbonyl Group......Page 787
  Oxidations Based on Sulfoxides......Page 790
  Oxidations with the Dess-Martin Periodinane,......Page 792
  Oxidation by Hydride Transfer to an Acceptor p Bond......Page 793
  Oxidations Catalyzed by Stable Nitroxyl Free Radicals......Page 795
  Oxidations with Molecular Oxygen......Page 797
 18.5 Oxidations to Carboxylic Acids......Page 799
 18.6 Oxidation of Ethers and Amines......Page 804
 18.7 Oxidative Rearrangements......Page 807
  Insertion of Oxygen into a C—C s Bond: The Baeyer-Villiger Oxidation......Page 809
  Insertion of Nitrogen into a C—C s Bond of an Aldehyde or Ketone: The Beckmann and Schmidt Rearrangements......Page 811
  Oxidative Rearrangements in Carboxylic Acids: The Hofmann, Curtius, and Lossen Rearrangements......Page 813
 18.8 Oxidation of Unsaturated Hydrocarbons......Page 816
  Oxidation of Alkenes by Addition......Page 817
  Oxidative Cleavage of Vicinal Diols......Page 830
  Ozonolysis and Its Alternatives......Page 831
  Oxidation Adjacent to p Bonds......Page 836
  Oxidation at the a Carbon of Carbonyl Compounds and Nitriles......Page 843
 18.11 Oxidation of Alkanes......Page 849
 18.12 A Catalogue of Oxidation Reactions: Oxidation at a Glance......Page 853
 Additional Problems......Page 857
 19.2 Catalytic Hydrogenation......Page 870
  Factors Affecting Reactivity in Catalytic Hydrogenation......Page 872
  Homogeneous Catalytic Hydrogenation of Alkenes......Page 878
  Hydrogenation of Alkynes......Page 881
  Hydrogenation of Carbonyl Compounds......Page 883
  Hydrogenation of Nitrogen-Containing Functional Groups......Page 885
  Transfer Hydrogenation, Ionic Hydrogenation, and Organocatalysis......Page 887
 19.3 Hydrogenolysis......Page 892
  Reductive Desulfurization of Dithioketals and Dithioacetals......Page 896
 Additional Problems......Page 898
  Nucleophilic Complex Metal Hydrides......Page 906
  Electrophilic Hydride Reducing Agents......Page 915
 20.2 Reduction by Hydrogen Transfer from Carbon......Page 920
  The Meerwein-Ponndorf-Verley Reduction (G = O, M = Al)......Page 921
  The Cannizzaro and Tishchenko Reactions (G = O, M = Na or Al)......Page 923
 20.3 Stereochemistry and Stereoselectivity in Hydride Reductions......Page 925
 20.4 Reduction Using Metals......Page 927
  Dissolving Metal Reduction of Carbonyl Compounds......Page 928
  The Pinacol Reaction and Related Reactions......Page 929
  Reductive Elimination: The E1cb Elimination......Page 931
  Wurtz Coupling......Page 933
  Birch Reduction......Page 934
  A Final Word on Dissolving Metal Reductions......Page 937
  The Wolff-Kishner Reduction and Related Reactions......Page 939
  Silicon-Based Deoxygenations......Page 944
  Reduction of Halides and Alcohols to Alkanes......Page 945
 20.6 A Catalog of Reduction Reactions: Reduction at a Glance......Page 947
 Additional Problems......Page 950
 21.1 Asymmetric Redox Reactions: An Overview......Page 958
 21.2 Sharpless Asymmetric Epoxidation of Allylic Alcohols......Page 959
  Effects of Alcohol Structure......Page 960
  Catalyst Structure......Page 961
  Kinetic Resolution of Racemic Allylic Alcohols......Page 962
  Jacobsen Catalysts......Page 965
  Katsuki Catalysts......Page 968
  Chiral Oxaziridines......Page 970
  Chiral Dioxiranes......Page 974
  Asymmetric Epoxidation of Conjugated Carbonyl Compounds Using Chiral Phase Transfer Catalysts......Page 976
  A Final Word on Epoxidation: What’s Missing, and Which Method?......Page 978
 21.5 Asymmetric Dihydroxylation......Page 980
  Kinetic Resolution of Racemates......Page 982
  Hydrolytic Kinetic Resolution: Epoxides......Page 983
  Oxidative Kinetic Resolution: Alcohols......Page 984
 21.7 Enantioselective Insertion into C—C and C—H Bonds......Page 987
 21.8 Asymmetric Hydrogenation......Page 988
  Oxazaborolidine-Catalyzed Asymmetric Reduction by Borane......Page 995
  Reduction with Trialkylboranes (G=CR2, M=B)......Page 996
 21.10 Enzymes: Biocatalysis of Redox Reactions......Page 998
 Chapter Summary......Page 1000
 Additional Problems......Page 1001
 22.1 Introduction......Page 1008
  Classification, Structure, and Bonding......Page 1009
  Silicon as a Surrogate for Hydrogen Bound to Carbon......Page 1014
  Silicon as a Surrogate for Hydrogen on Oxygen: Silyl Ethers......Page 1018
  Silyl Enol Ethers......Page 1019
 22.3 Heteroatom-Centered Nucleophiles: Silyllitihiums, Stannyllithiums, Sulfides, and Selenides......Page 1023
  Conjugate Additions......Page 1024
 22.4 Reactions of Organophosphorus, Organosulfur, and Organoselenium Compounds......Page 1025
  SN2 Displacement of Alcohols......Page 1026
  The Corey-Winter Elimination......Page 1027
  The Perkow Rearrangement......Page 1029
  Sigmatropic Rearrangements of Allylic Sulfoxides, Sulfonium Ylides, and Selenoxides: The Mislow-Evans Rearrangement......Page 1031
  The Pummerer Rearrangement......Page 1032
  Sulfur Dioxide Extrusion: Ramberg-Bäcklund Reaction......Page 1034
 Chapter Summary......Page 1036
 Additional Problems......Page 1037
  Chiral Auxiliaries......Page 1042
  Chiral Catalysis......Page 1044
  Simple Diastereoselection and Double Diastereoselection......Page 1045
 23.2 Asymmetric Synthesis with Chiral Auxiliaries: Additions......Page 1053
  The Asymmetric Aldol Addition......Page 1054
  The Asymmetric Diels-Alder Reaction......Page 1059
  Asymmetric Additions to Imines......Page 1063
  Asymmetric Conjugate Additions......Page 1065
 23.3 Asymmetric Substitution at Carbon: Alkylation of Enolates and Related Nucleophiles......Page 1066
  SAMP/RAMP Hydrazones......Page 1067
  Chiral Oxazolines......Page 1069
 23.4 Catalytic Asymmetric Synthesis......Page 1070
  Chiral Activation and Deactivation......Page 1072
  Asymmetric Cycloadditions......Page 1074
  Asymmetric Aldol Reactions......Page 1076
  Organocatalysis......Page 1077
 23.5 Representative Asymmetric Syntheses......Page 1081
  The Enantioselective Total Synthesis of Salicylihalamides A and B......Page 1082
  The Enantioslective Synthesis of Aigialomycin D......Page 1084
  The Enantioselective Synthesis of Chinesiolide B......Page 1087
  The Enantioselective Synthesis of Plakortethers F and G......Page 1090
  The Asymmetric Synthesis of a Proposed Structure of Iriomoteolide-1b......Page 1092
  An Enantioselective Synthesis of Manzacidin-C......Page 1097
  A Final Chapter: The Enantioselective Synthesis of Ecklonialactones......Page 1098
 Additional Problems......Page 1101
Appendix 1: Named Reactions, Named Reagents, and Named Rules......Page 1110
Appendix 2: Glossary of Key Terms......Page 1134
Appendix 3: Selected Physical Constants......Page 1148
Index......Page 1152