References to Organic Chemistry, 2nd Ed. By Maitland Jones, Jr., W.W. Norton & Co., 2000
Chapter 1 Atoms and Molecules; Orbitals and Bonding
1.1 Atoms and Atomic Oribitals pp. 2-4
1.2 Covalent Bonds and Lewis Structures pp. 4-13
1.3 Introduction to Resonance Forms pp. 13-18
1.4 More on Atomic Orbitals pp. 18-25
1.5 The Covalent Bond: Hydrogen (H2) pp. 25-31
1.6 Bond Strength pp. 31-37
1.7 An Introduction to Reactivity: Acids and Bases pp. 37-38
Chapter 2 Alkanes
2.1 The Structure of Methane (CH4) pp. 46-50
2.2 Hybrid Orbitals: Making a Better Model for Methane pp. 50-57
2.3 Derivatives of Methane: Methyl Compounds (CH3X) pp. 57-59
2.4 The Methyl Cation, Anion, and Radical pp. 59-61
2.5 Ethane, Ethyl Compounds and Newman Projections pp. 61-67
2.6 Structure Drawings pp. 67-68
2.7 Propane and Propyl Compounds pp. 68-70
2.8 Butanes and Butyl Compounds, and Conformational Analysis pp.
71-74
2.9 Pentanes and Pentyl Compounds pp. 75-77
2.10 The Naming Conventions for Alkanes pp. 77-79
2.11 Writing Isomers pp. 79-81
2.12 Rings pp. 81-85
2.14 13C Nuclear Magnetic Resonance Spectroscopy pp. 87-88
Chapter 3 Alkenes and Alkynes
3.1 Alkenes: Structure and Bonding pp. 93-101
3.2 Derivatives, Isomers and Names of Alkenes pp. 101-104
3.3 Nomenclature pp. 104-106
3.4 The Cahn-Ingold-Prelog Priority System pp. 106-109
3.5 Relative Stability of Alkenes: Heats of Formation pp. 110-112
3.6 Double Bonds in Rings pp. 112-117
3.8 Alkynes: Structure and Bonding pp. 118-120
3.9 Relative Stability of Alkynes: Heats of Formation pp. 121
3.10 Derivatives and Isomers of Alkynes pp. 121-122
3.11 Triple Bonds in Rings pp. 123
3.13 Acidity of Alkynes pp. 124-125
3.14 Molecular Formulas and Degrees of Unsaturation pp. 125-126
Chapter 4 Stereochemistry
4.1 Chirality pp. 132-134
4.2 Properties of Enantiomers: Physical Differences pp. 134-136
4.3 The (R/S) Convention pp. 136-140
4.4 The Physical Basis of Optical Activity pp. 140-142
4.5 Properties of Enantiomers: Chemical Differences pp. 142-146
4.6Interconversion of Enantiomers by Mobile Equilibrium: Gauche
Butane pp. 146-147
4.7Diastereomers: Molecules Containing More Than One Stereogenic
Center pp. 147-152
4.8 Physical Properties of Diastereomers: Optical Resolution pp.
153-155
4.9 Determination of Absolute Configuration (R or S) pp. 155-156
4.10 Stereochemical Analysis of Ring Compounds pp. 156-158
4.11 Review of Isomerism pp. 159-161
Chapter 5 Rings
5.1 Rings and Strain pp. 168-175
5.2 Quantitative Evaluation of Strain Energy pp. 176-180
5.3 Stereochemistry of Cyclohexane: Conformational Analysis pp.
180-182
5.4 Monosubstituted Cyclohexanes pp. 182-187
5.5 Disubstituted Ring Compounds pp. 187-195
5.6 Bicyclic Compounds pp. 195-200
Chapter 6 Substitution and Elimination Reactions: The SN2, SN1,
E2 and E1 Reactions
6.1 Alkyl Halides: Nomenclature and Structure pp. 208-210
6.2 Reaction Mechanism: Brønsted Acids and Bases pp.
210-211
6.3 The Arrow Formalism pp. 212-213
6.4 Lewis Acids and Bases pp. 214-215
6.5 HOMO-LUMO Interactions pp. 215-216
6.6 Reactions of Alkyl Halides: The Substitution Reaction pp.
216-217
6.7 Substitution, Nucleophilic, Bimolecular: The SN2 Reaction pp.
217-237
6.9 Substitution, Nucleophilic, Unimolecular: The SN1 Reaction pp.
237-244
6.10 Overview of the SN2 and SN1 Reactions pp. 244-246
6.11 The Unimolecular Elinination Reaction: E1 pp. 247-249
6.12 The Biomolecular Elimination Reaction: E2 pp. 249-261
6.13 Synthetic Utility pp. 261-263
Chapter 7 Equilibria
7.1 Equilibrium pp.275-278
7.2 Gibbs Standard Free Energy Change pp. 278-280
7.3 Rates of Chemical Reactions pp. 280-282
7.4 Rate Constant pp. 282-283
7.5Energy Barriers in Chemical Reactions: The Transition State and
Activation Energy pp. 283-290
7.6 Reaction Mechanism pp. 290-292
7.7 The Hammond Postulate: Thermodynamics vs Kinetics pp. 292-298
Chapter 8 Additions to Alkenes 1
8.1 Electronegativity pp. 306-307
8.2 Mechanism of the Addition of Hydrogen Halides to Alkenes pp.
307-310
8.3 Regiochemistry pp. 310-311
8.4 Resonance Effects pp. 311-316
8.5 Review of Resonance: How to Write Resonance Forms pp. 317-322
8.6 Resonance and the Stability of Carbocations pp. 322-327
8.7 Inductive Effects on Addition Reactions pp. 327-329
8.8 H-X Addition Reactions: Hydration pp. 329-332
8.9 Dimerization and Polymerization of Alkenes pp. 333-335
8.10 Hydroboration pp. 335-343
8.11 Utility of Hydroboration: Alcohol Formation pp. 344-346
8.12 Rearrangements During H-X Addition to Alkenes pp. 346-350
Chapter 9 Additions to Alkenes 2; Additions to Alkynes
9.1 Addition of X2 Reagents pp. 359-370
9.2 Hydration Through Mercury Compounds: Oxymercuration pp.
370-373
9.3Other Addition Reactions Involving Three-Membered Rings: Oxiranes
and Cyclopropanes pp. 373-386
9.4 Dipolar Addition Reactions pp. 386-394
9.5 Addition Reactions of Alkynes: H-X Addition pp. 394-398
9.6 Addition of X2 Reagents to Alkynes p. 398
9.7 Hydration of Alkynes pp. 398-400
9.8 Hydroboration of Alkynes pp. 400-402
9.9 Hydrogenation of Alkynes: Syn Hydrogenation pp. 402-403
9.10 Reduction by Sodium in Ammonia: Anti Hydrogenation pp. 403-405
Chapter 10 Radical Reactions
10.1 Formation and Simple Reactions of Radicals pp. 418-426
10.2 Structure of Radicals pp. 426-427
10.3 Stability of Radicals pp. 427-430
10.4 Radical Addition to Alkenes pp. 430-438
10.5 Other Radical Additon Reactions pp. 438-440
10.7 Photohalogenation pp. 441-448
10.8 Allylic Halogenation pp. 448-452
10.9 Rearrangements (and Nonrearrangements) of Radicals pp. 452-456
Chapter 11 Dienes and the Allyl System: 2p Orbitals in
Conjuation
11.1 Allenes: 1,2-Dienes pp. 466-468
11.2 Related Systems: Ketenes and Cumulenes pp.468-469
11.3 Allenes as Intermediates in the Isomerism of Acetylenes pp.
469-472
11.4 1,3-Dienes pp. 472-475
11.5 The Physical Consequences of Conjugation pp. 475-480
11.6 Molecular Orbitals and Ultraviolet Spectroscopy pp. 480-486
11.8 The Chemical Consequences of Conjugation: Addition Reactions of
Dienes pp. 489-491
11.9 Thermodynamic and Kinetic Control of Addition Reactions pp.
491-495
11.10 The Allyl System: Three Ovelapping 2p Orbitals pp. 495-496
11.11 The Allyl Cation: SN1 Solvolysis of Allylic Halides pp.
496-497
11.12 SN2 Reactions of Allylic Halides pp. 497-499
11.13 The Allyl Radical p. 499
11.14 The Allyl Anion pp. 499-500
11.15 The Diels-Alder Reaction of Dienes pp. 500-510
Chapter 12 Conjugation and Aromaticity
12.1 The Structure of Benzene pp. 528-530
12.2 A Resonance Picture of Benzene pp. 530-533
12.3 The Molecular Orbital Picture of Benzene pp. 533-534
12.4 Quantitative Evlauations of Resonance Stabilization in Benzene
pp. 535-537
12.5 A Generalization of Aromaticity: Hückel's 4n + 2 Rule pp.
537-550
12.6 Annulenes pp. 550-551
12.7 Substituted Benzenes pp. 551-554
12.9 Heterobenzenes and Other Heterocyclic Aromatic Compounds pp.
555-556
12.10 Polynuclear Aromatic Compounds pp. 556-559
12.11 Introduction to the Chemistry of Benzene pp. 559-563
12.12The Benzyl Group and Its Reactivity: Activation of the Adjacent
(Benzyl) Position by Benzene Rings pp. 563-567
Chapter 13 Substitution Reactions of Aromatic Compounds
13.1 Addition Reactions of Benzenes to Give Nonaromatic Compounds:
Hydrogenation pp. 576 578
13.2 Diels-Alder Reactions pp. 578-580
13.3 Other Addition Reactions pp. 580-582
13.4 Substitution Reactions of Benzene pp. 582-584
13.5 Electrophilic Aromatic Substitution pp. 585-589
13.6 The Friedel-Crafts Alkylation Reaction pp. 589-593
13.7 Friedel-Crafts Acylation pp. 593-596
13.8 Stable Carbocations in "Superacid" pp. 596-598
13.9 Summary of Simple Aromatic Substitution: What We Can Do So Far
pp. 598-602
13.10 Disubstituted Benzenes: Ortho, Meta, and Para Substitution pp.
602-614
13.11 Inductive Effects in Aromatic Substitution pp. 614-617
13.12Polysubstitution of Aromatic Compounds and Synthesis of Multiply
Substituted Benzenes pp. 617-622
13.13 Nucleophilic Aromatic Substitution pp. 622-625
13.14 Benzyne pp. 625-627