Organic Chemistry

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ISBN: 9780393989212 | 0393989216
Cover: Hardcover
Copyright: 8/1/2000

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Shaped by Maitland Jones's years of classroom experience at Princeton University, Organic Chemistry remains committed to helping students understand--rather than memorize--the fundamental concepts of organic chemistry. Retaining the authoritative coverage, informal style, and abundance of carefully annotated figures of its predecessors, this Third Edition strives for even greater accessibility with a clean new design, new pedagogy, and enhanced treatment of topics like acids and bases, synthesis, and spectroscopy.

Preface	p. xxvii
Introduction	p. xxxv
Atoms and Molecules; Orbitals and Bonding	p. 1
Atoms and Atomic Orbitals	p. 2
Covalent Bonds and Lewis Structures	p. 4
Introduction to Resonance Forms	p. 13
More on Atomic Orbitals	p. 18
The Covalent Bond: Hydrogen (H[subscript 2])	p. 25
Bond Strength	p. 31
An Introduction to Reactivity: Acids and Bases	p. 37
Quantum Mechanics and Babies	p. 38
Summary	p. 39
Additional Problems	p. 41
Alkanes	p. 45
The Structure of Methane (CH[subscript 4])	p. 46
Hybrid Orbitals: Making a Better Model for Methane	p. 50
Derivatives of Methane: Methyl (CH[subscript 3]) and Methyl Compounds (CH[subscript 3]X)	p. 57
The Methyl Cation ([superscript +]CH[subscript 3]), Anion ([superscript -]:CH[subscript 3]), and Radical (.CH[subscript 3])	p. 59
Ethane (C[subscript 2]H[subscript 6]), Ethyl Compounds (C[subscript 2]H[subscript 5]X), and Newman Projections	p. 61
Structure Drawings	p. 67
Propane (C[subscript 3]H[subscript 8]) and Propyl Compounds (C[subscript 3]H[subscript 7]X)	p. 68
Butanes (C[subscript 4]H[subscript 10]), Butyl Compounds (C[subscript 4]H[subscript 9]X), and Conformational Analysis	p. 71
Pentanes (C[subscript 5]H[subscript 12]) and Pentyl Compounds (C[subscript 5]H[subscript 11]X)	p. 75
The Naming Conventions for Alkanes	p. 77
Writing Isomers	p. 79
Rings	p. 81
Physical Properties of Alkanes and Cycloalkanes	p. 85
[superscript 13]C Nuclear Magnetic Resonance Spectroscopy	p. 87
Alkanes as Biomolecules	p. 88
Summary	p. 89
Additional Problems	p. 90
Alkenes and Alkynes	p. 93
Alkenes: Structure and Bonding	p. 93
Derivatives, Isomers, and Names of Alkenes	p. 101
Nomenclature	p. 104
The Cahn-Ingold-Prelog Priority System	p. 106
Relative Stability of Alkenes: Heats of Formation	p. 110
Double Bonds in Rings	p. 112
Physical Properties of Alkenes	p. 117
Alkynes: Structure and Bonding	p. 118
Relative Stability of Alkynes: Heats of Formation	p. 121
Derivatives and Isomers of Alkynes	p. 121
Triple Bonds in Rings	p. 123
Physical Properties of Alkynes	p. 124
Acidity of Alkynes	p. 124
Molecular Formulas and Degrees of Unsaturation	p. 125
Alkenes and Biology	p. 126
Summary	p. 128
Additional Problems	p. 129
Stereochemistry	p. 131
Chirality	p. 132
Properties of Enantiomers: Physical Differences	p. 134
The (R/S) Convention	p. 136
The Physical Basis of Optical Activity	p. 140
Properties of Enantiomers: Chemical Differences	p. 142
Interconversion of Enantiomers by Mobile Equilibria: Gauche Butane	p. 146
Diastereomers: Molecules Containing More Than One Stereogenic Atom	p. 147
Physical Properties of Diastereomers: Optical Resolution	p. 153
Determination of Absolute Configuration (R or S)	p. 155
Stereochemical Analysis of Ring Compounds (a Beginning)	p. 156
Review of Isomerism	p. 159
Chirality without "Four Different Groups Attached to One Carbon"	p. 161
Stereochemistry in the Real World: Thalidomide; The Consequences of Being Wrong-Handed	p. 163
Summary	p. 164
Additional Problems	p. 165
Rings	p. 167
Rings and Strain	p. 168
Quantitative Evaluation of Strain Energy	p. 176
Stereochemistry of Cyclohexane: Conformational Analysis	p. 180
Monosubstituted Cyclohexanes	p. 182
Disubstituted Ring Compounds	p. 187
Bicyclic Compounds	p. 195
Polycyclic Systems	p. 201
Adamantanes in Materials and Biology	p. 201
Summary	p. 203
Additional Problems	p. 204
Substitution and Elimination Reactions: The S[subscript N]2, S[subscript N]1, E2, and E1 Reactions	p. 207
Alkyl Halides: Nomenclature and Structure	p. 208
Reaction Mechanism: Br[o slash]nsted Acids and Bases	p. 210
The Arrow Formalism	p. 212
Lewis Acids and Bases	p. 214
HOMO-LUMO Interactions	p. 215
Reactions of Alkyl Halides: The Substitution Reaction	p. 216
Substitution, Nucleophilic, Bimolecular: The S[subscript N]2 Reaction	p. 217
The S[subscript N]2 Reaction in Biochemistry	p. 236
Substitution, Nucleophilic, Unimolecular: The S[subscript N]1 Reaction	p. 237
Overview of the S[subscript N]2 and S[subscript N]1 Reactions	p. 244
The Unimolecular Elimination Reaction: E1	p. 247
The Bimolecular Elimination Reaction: E2	p. 249
What Can We Do with These Reactions? Synthetic Utility	p. 261
Summary	p. 263
Additional Problems	p. 266
Equilibria	p. 273
Equilibrium	p. 275
Gibbs Standard Free Energy Change	p. 278
Rates of Chemical Reactions	p. 280
Rate Constant	p. 282
Energy Barriers in Chemical Reactions: The Transition State and Activation Energy	p. 283
Reaction Mechanism	p. 290
The Hammond Postulate: Thermodynamics versus Kinetics	p. 292
Enzymes and Reaction Rates	p. 299
Summary	p. 300
Additional Problems	p. 302
Additions to Alkenes 1	p. 305
Electronegativity	p. 306
Mechanism of the Addition of Hydrogen Halides to Alkenes	p. 307
Regiochemistry	p. 310
Resonance Effects	p. 311
Review of Resonance: How to Write Resonance Forms	p. 317
Resonance and the Stability of Carbocations	p. 322
Inductive Effects on Addition Reactions	p. 327
H--X Addition Reactions: Hydration	p. 329
Dimerization and Polymerization of Alkenes	p. 333
Hydroboration	p. 335
Utility of Hydroboration: Alcohol Formation	p. 344
Rearrangements During H--X Addition to Alkenes	p. 346
Rearrangements in Biological Processes	p. 350
Summary	p. 351
Additional Problems	p. 354
Additions to Alkenes 2; Additions to Alkynes	p. 359
Addition of X[subscript 2] Reagents	p. 359
Hydration Through Mercury Compounds: Oxymercuration	p. 370
Other Addition Reactions Involving Three-Membered Rings: Oxiranes and Cyclopropanes	p. 373
Dipolar Addition Reactions	p. 386
Addition Reactions of Alkynes: H--X Addition	p. 394
Addition of X[subscript 2] Reagents to Alkynes	p. 398
Hydration of Alkynes	p. 398
Hydroboration of Alkynes	p. 400
Hydrogenation of Alkynes: Syn Hydrogenation	p. 402
Reduction by Sodium in Ammonia: Anti Hydrogenation	p. 403
Three-membered Rings in Biochemistry	p. 405
Summary	p. 406
Additional Problems	p. 410
Radical Reactions	p. 417
Formation and Simple Reactions of Radicals	p. 418
Structure of Radicals	p. 426
Stability of Radicals	p. 427
Radical Addition to Alkenes	p. 430
Other Radical Addition Reactions	p. 438
Radical-Initiated Addition of HBr to Alkynes	p. 440
Photohalogenation	p. 441
Allylic Halogenation	p. 448
Rearrangements (and Nonrearrangements) of Radicals	p. 452
Radicals in Your Body: Do Free Radicals Age Us?	p. 456
Summary	p. 456
Additional Problems	p. 460
Dienes and the Allyl System; 2p Orbitals in Conjugation	p. 465
Allenes: 1,2-Dienes	p. 466
Related Systems: Ketenes and Cumulenes	p. 468
Allenes as Intermediates in the Isomerization of Acetylenes	p. 469
1,3-Dienes	p. 472
The Physical Consequences of Conjugation	p. 475
Molecular Orbitals and Ultraviolet Spectroscopy	p. 480
Polyenes and Vision	p. 486
The Chemical Consequences of Conjugation: Addition Reactions of Dienes	p. 489
Thermodynamic and Kinetic Control of Addition Reactions	p. 491
The Allyl System: Three Overlapping 2p Orbitals	p. 495
The Allyl Cation: S[subscript N]1 Solvolysis of Allylic Halides	p. 496
S[subscript N]2 Reactions of Allylic Halides	p. 497
The Allyl Radical	p. 499
The Allyl Anion	p. 499
The Diels-Alder Reaction of Dienes	p. 500
Biosynthesis of Terpenes	p. 510
Steroid Biosynthesis	p. 515
Summary	p. 520
Additional Problems	p. 522
Conjugation and Aromaticity	p. 527
The Structure of Benzene	p. 528
A Resonance Picture of Benzene	p. 530
The Molecular Orbital Picture of Benzene	p. 533
Quantitative Evaluations of Resonance Stabilization (Delocalization Energy) in Benzene	p. 535
A Generalization of Aromaticity: Huckel's 4n + 2 Rule	p. 537
Annulenes	p. 550
Substituted Benzenes	p. 551
Physical Properties of Substituted Benzenes	p. 554
Heterobenzenes and other Heterocyclic Aromatic Compounds	p. 555
Polynuclear Aromatic Compounds	p. 556
Introduction to the Chemistry of Benzene	p. 559
The Benzyl Group and Its Reactivity: Activation of the Adjacent (Benzyl) Position by Benzene Rings	p. 563
The Bio-downside: The Mechanism of Carcinogenesis by Polycyclic Aromatic Compounds	p. 567
Summary	p. 570
Additional Problems	p. 572
Substitution Reactions of Aromatic Compounds	p. 575
Addition Reactions of Benzenes to Give Nonaromatic Compounds: Hydrogenation	p. 576
Diels-Alder Reactions	p. 578
Other Addition Reactions	p. 580
Substitution Reactions of Benzene	p. 582
Electrophilic Aromatic Substitution	p. 585
The Friedel-Crafts Alkylation Reaction	p. 589
Friedel-Crafts Acylation	p. 593
Stable Carbocations in "Superacid"	p. 596
Summary of Simple Aromatic Substitution: What We Can Do So Far	p. 598
Disubstituted Benzenes: Ortho, Meta, and Para Substitution	p. 602
Inductive Effects in Aromatic Substitution	p. 614
Polysubstitution of Aromatic Compounds and Synthesis of Multiply Substituted Benzenes	p. 617
Nucleophilic Aromatic Substitution	p. 622
Benzyne	p. 625
Biological Synthesis of Aromatic Rings: Phenylalanine	p. 627
Summary	p. 630
Additional Problems	p. 633
Analytical Chemistry	p. 637
Chromatography	p. 638
Mass Spectrometry	p. 641
Infrared Spectroscopy	p. 649
Nuclear Magnetic Resonance Spectroscopy	p. 656
Survey of NMR Spectra of Organic Molecules	p. 666
Spin-Spin Coupling: The Coupling Constant, J	p. 670
More Complicated Spectra	p. 678
Decoupled Spectra	p. 682
Nuclear Magnetic Resonance Spectra of Other Nuclei	p. 684
Determination of the Structure of a Complex Biomolecule: Maitotoxin	p. 685
Dynamic NMR	p. 686
Summary	p. 690
Additional Problems	p. 691
Carbonyl Chemistry 1: Addition Reactions	p. 701
Structure of the Carbon-Oxygen Double Bond	p. 701
Nomenclature of Carbonyl Compounds	p. 704
Physical Properties of Carbonyl Compounds	p. 707
Spectroscopy of Carbonyl Compounds	p. 707
Reactions of Carbonyl Compounds: Simple Reversible Additions	p. 710
Equilibrium in Addition Reactions	p. 715
Other Addition Reactions: Additions of Cyanide and Bisulfite	p. 720
Addition Reactions Followed by Water Loss: Acetal and Ketal Formation	p. 721
Addition Reactions of Nitrogen Bases: Imine and Enamine Formation	p. 727
Organometallic Reagents	p. 734
Irreversible Addition Reactions	p. 737
Oxidation of Alcohols to Carbonyl Compounds	p. 742
The Wittig Reaction	p. 745
Biological Oxidation	p. 748
Summary	p. 751
Additional Problems	p. 756
The Chemistry of Alcohols Summarized and Extended: Glycols, Ethers, and Related Sulfur Compounds	p. 761
Nomenclature	p. 762
Structure of Alcohols	p. 763
Physical Properties of Alcohols	p. 764
Spectroscopic Properties of Alcohols	p. 765
Acid and Base Properties of Alcohols	p. 766
Reactions of Alcohols	p. 770
Syntheses of Alcohols	p. 777
Dialcohols: Diols or Glycols	p. 779
Ethers	p. 785
Syntheses of Ethers	p. 787
Reactions of Ethers	p. 791
Thiols (Mercaptans) and Thioethers (Sulfides)	p. 797
Reactions and Syntheses of Thiols and Sulfides	p. 799
Crown Ethers	p. 804
Summary	p. 806
Additional Problems	p. 812
Carbonyl Chemistry 2: Reactions at the [alpha]-Position	p. 817
Aldehydes and Ketones Are Weak Bronsted Acids	p. 818
Reactions of Enols and Enolates	p. 828
Condensation Reactions of Carbonyl Compounds: The Aldol Condensation	p. 840
Reactions Related to the Aldol Condensation	p. 850
Problem Solving	p. 862
Carbonyl Compounds without [alpha]-Hydrogens: Magid's Third Rule	p. 865
The Aldol Condensation in the Real World: Introduction to Modern Synthesis	p. 871
Summary	p. 875
Additional Problems	p. 879
Carboxylic Acids	p. 887
Nomenclature and Properties of Carboxylic Acids	p. 888
Structure of Carboxylic Acids	p. 890
Infrared and Nuclear Magnetic Resonance Spectra of Carboxylic Acids	p. 891
Acidity and Basicity of Carboxylic Acids	p. 892
Reactions of Carboxylic Acids	p. 896
Reactivity of Carboxylic Acids at the [alpha]-Position	p. 917
Syntheses of Carboxylic Acids	p. 923
Fatty Acids	p. 925
Summary	p. 928
Additional Problems	p. 932
Derivatives of Carboxylic Acids: Acyl Compounds	p. 937
Nomenclature	p. 938
Physical Properties and Structures of Acyl Compounds	p. 943
Spectral Characteristics	p. 947
Reactions of Acid Chlorides	p. 949
Reactions of Anhydrides	p. 953
Addition-Elimination Reactions of Esters	p. 955
Reactions of Amides	p. 960
Reactions of Nitriles	p. 963
Reactions of Ketenes	p. 966
Enolate Chemistry of Esters: The Claisen and Related Condensation Reactions	p. 967
Variations on the Claisen Condensation	p. 974
Forward and Reverse Claisen Condensations in Biology	p. 979
Reactions of [beta]-Keto Esters	p. 982
Complicated "Fun in Base" Problems	p. 988
New Synthetic Routes to Acyl Compounds	p. 989
Thermal Elimination Reactions of Esters	p. 994
Summary	p. 998
Additional Problems	p. 1004
Introduction to the Chemistry of Nitrogen-Containing Compounds: Amines	p. 1011
Nomenclature	p. 1012
Structure and Physical Properties of Amines	p. 1016
Spectroscopic Properties of Amines	p. 1020
Acid and Base Properties of Amines	p. 1021
Reactions of Amines	p. 1026
Syntheses of Amines	p. 1038
Alkaloids	p. 1047
Synthesis of Quinine	p. 1051
Phase-Transfer Catalysis: Ammonium Ions in Synthesis	p. 1052
Summary	p. 1054
Additional Problems	p. 1058
Aromatic Transition States: Orbital Symmetry	p. 1063
Concerted Reactions	p. 1064
Electrocyclic Reactions	p. 1066
Cycloaddition Reactions	p. 1075
Sigmatropic Shift Reactions	p. 1081
Sigmatropic Shifts of Carbon	p. 1091
Other Sigmatropic Shifts	p. 1095
A Biological Cope Rearrangement	p. 1099
A Molecule with a Fluxional Structure	p. 1100
Summary	p. 1108
Additional Problems	p. 1110
Introduction to Polyfunctional Compounds: Intramolecular Reactions and Neighboring Group Participation	p. 1117
Heteroatoms as Neighboring Groups	p. 1119
Neighboring [pi] Systems	p. 1132
Single Bonds as Neighboring Groups	p. 1146
Coates' Cation	p. 1156
A Family of Concerted Rearrangements of Acyl Compounds	p. 1157
Summary	p. 1163
Additional Problems	p. 1165
Polyfunctional Natural Products: Carbohydrates	p. 1169
Nomenclature and Structure	p. 1170
Reactions of Sugars	p. 1181
The Ring Size in Glucose	p. 1196
The Fischer Determination of the Structure of D-Glucose (and the 15 Other Aldohexoses)	p. 1197
An Introduction to Di- and Polysaccharides	p. 1205
Summary	p. 1211
Additional Problems	p. 1213
Introduction to the Chemistry of Heterocyclic Molecules	p. 1215
Three-Membered Heterocycles: Oxiranes (Epoxides), Thiiranes (Episulfides), and Aziridines	p. 1216
Four-Membered Heterocycles: Oxetanes, Thietanes, and Azetidines	p. 1224
Five- and Six-Membered Heterocycles	p. 1225
Nonaromatic Heterocycles Containing More Than One Heteroatom	p. 1227
Nitrogen-Containing Aromatic Heterocyclic Compounds	p. 1230
Other Aromatic Heterocycles: Furan and Thiophene	p. 1244
Aromatic Heterocycles Containing More Than One Heteroatom	p. 1247
Two-Ring Heterocycles	p. 1247
Bioactive Heterocycles: Penicillin and Related Antibiotics	p. 1253
Summary	p. 1257
Additional Problems	p. 1263
Introduction to Amino Acids and Polyamino Acids (Peptides and Proteins)	p. 1269
Amino Acids	p. 1270
Reactions of Amino Acids	p. 1282
Peptide Chemistry	p. 1284
Nucleosides, Nucleotides, and Nucleic Acids	p. 1305
Summary	p. 1310
Additional Problems	p. 1314
Key Terms	p. 1
Some Commonly Used Abbreviations	p. 22
Index	p. 23
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Organic Chemistry

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