Chapter 0
Students Guide to Succcess in Organic Chemistry
0.1 What is Organic Chemistry? 4
0.2 Organic Chemistry in the Everyday World 9
0.3 Organic Chemists are People, Too 11
0.4 Learning to Think Like a Chemist 14
0.5 Developing Study Methods for Success 15
Key Ideas from Chapter 0 18
Chapter 1
Atoms, Orbitals, and Bonds
1.1 The Periodic Table 21
1.2 Atomic Structure 22
1.3 Energy Levels and Atomic Orbitals 23
1.4 How Electrons Fill Orbitals 27
1.5 Bond Formation 28
1.6 Molecular Orbitals 30
1.7 Orbital Hybridization 35
1.8 Multiple Bonding 46
1.9 Drawing Lewis Structures 49
1.10 Polar Covalent Bonds 54
1.11 Inductive Effects on Bond Polarity 57
1.12 Formal Charges 58
1.13 Resonance 60
Key Ideas from Chapter 1 66
Chapter 2
Introduction to Organic Nomenclature and Functional Groups
2.1 Drawing Organic Structures 73
2.2 Alkanes 77
2.3 Structural Isomerism 77
2.4 IUPAC Nomenclature 79
2.5 Naming Alkanes 80
2.6 Naming Cycloalkanes 87
2.7 Naming Complex Alkyl Groups 91
2.8 Functional Groups 97
2.9 Naming Alkenes and Alkynes 100
2.10 Naming Alkenes, Part II 108
2.11 Arenes 109
2.12 Organohalogens 113
2.13 Using Molecular Formulas 115
Key Ideas from Chapter 2 117
Chapter 3
Molecular Conformations
3.1 Representing Three-Dimensional Molecules in Two
Dimensions 125
3.2 Dihedral Angles 127
3.3 The Conformations of Ethane 129
3.4 Conformational Analysis of Butane 131
3.5 Angle Strain in Cycloalkanes 134
3.6 Conformations of Cyclohexane 136
3.7 Conformational Inversion of Cyclohexane 142
3.8 Conformational Analysis of Monosubstituted
Cyclohexanes 143
3.9 Naming Stereoisomers 147
3.10 Conformational Analysis of Disubstituted
Cyclohexanes 149
Special Topic – Computer Modeling 155
3.11 Conformations of Other Cycloalkanes 157
3.12 Naming Polycyclic Ring Systems 159
3.13 Polycyclic Ring Systems 164
Sidebar - Higher Polycyclic Structures 166
Key Ideas from Chapter 3 168
Chapter 4
Physical Properties
of Organic Compounds
4.1 Phases of Matter 175
Sidebar - Liquid Crystals 178
4.2 Melting Points 179
4.3 Boiling Points 183
4.4 Solubility 190
Sidebar - Surfactants 194
4.5 Density 197
Key Ideas from Chapter 4 199
Chapter 5
Acid-Base Theory
5.1 Acids and Bases 209
5.2 Acid and Base Strength 215
5.3 Hard and Soft Acids and Bases 222
5.4 Organic Acids and Bases 226
5.5 Relative Acidity and Basicity 231
5.6 Substituent Effects on Acidity and Basicity 235
Key Ideas from Chapter 5 238
Chapter 6
Reaction Mechanisms
An Overview of Organic Chemistry
6.1 Chemical Equilibria and Rates 246
6.2 Equilibrium Thermodynamics 250
6.3 Reaction Kinetics 253
6.4 Reaction Profiles and Mechanisms 255
6.5 Why Reactions Occur 260
6.6 Organic Reaction Terminology 264
6.7 Classification of Reagents in Organic Reactions 270
6.8 Writing Reaction Mechanisms 270
6.9 Substitution Reactions 278
6.10 Addition Reactions 281
6.11 Elimination Reactions 284
Key Ideas from Chapter 6 287
Chapter 7
Nucleophilic Additions to the Carbonyl Group
7.1 Naming Carbon—Oxygen Double Bonds 299
7.2 Reactivity of the Carbonyl Group 304
7.3 Guide for Learning Organic Reactions 307
7.4 The Cyanohydrin Reaction 309
7.5 Addition of Water and Alcohols 311
7.6 Reaction with Nitrogen Nucleophiles 320
Sidebar - Biochemical Transamination 325
7.7 Reaction with Hydride Nucleophiles 326
7.8 Carbon Nucleophiles 331
Synthesis of Triphenylmethanol 336
7.9 Organic Synthesis 339
7.10 The Wittig Reaction 342
Synthesis of Methylene-4-tert-butylcyclohexane 344
Key Ideas from Chapter 7 348
Chapter 8-A
Reaction Summary I
A summary of the reactions learned in Chapters 7-8
Chapter 8
Nucleophilic Substitution on the Carbonyl
Group
8.1 The Acyl Transfer Mechanism 360
8.2 Water and Alcohol Nucleophiles 362
Synthesis of Isoamyl Acetate (Banana Oil) 366
8.3 Halide and Carboxylic Acid Nucleophiles 372
Sidebar - Aspirin and Acetaminophen 376
8.4 Reaction with Nitrogen Nucleophiles 381
8.5 Reaction with the Hydride Nucleophile 384
8.6 Carbon Nucleophiles 392
8.7 Nitriles 401
8.8 The Baeyer-Villiger Oxidation 406
Synthesis of Caprolactone 409
8.9 Solving Mechanistic Problems 410
Key Ideas from Chapter 8 414
Chapter 9
Infrared Spectroscopy
and
Mass Spectrometry
9.1 Electromagnetic Radiation and Spectroscopy 431
9.2 Molecular Vibrations in Infrared Spectroscopy 434
9.3 Introduction to Interpreting Infrared Spectra 436
9.4 Hydrogen Bonded to sp3 Hybrid Atoms 439
9.5 Hydrogen Bonded to sp2 and sp Hybrid Atoms 443
9.6 Carbon—Heteroatom Bonds 448
9.7 Other Bonds 452
9.8 Interpreting Infrared Spectra, Part 2 456
9.9 Mass Spectrometry 459
9.10 The Molecular Ion 463
Key Ideas from Chapter 9 467
Chapter 10
Nuclear Magnetic Resonance
10.1 Theory of Nuclear Magnetic Resonance 475
10.2 Shielding 478
10.3 Chemical Shift and Molecular Structure 480
10.4 Interpreting Proton NMR Spectra 484
10.5 Spin-Spin Splitting 491
10.6 Integration Signals in an NMR Spectrum 501
10.7 Analyzing an NMR Spectrum 503
Sidebar – Magnetic Resonance Imaging 511
10.8 Strategy for Solving Spectral Problems 513
Key Ideas from Chapter 10 519
Chirality
11.1 Symmetry and Asymmetry 532
11.2 Nomenclature of Stereocenters 538
11.3 Properties of Asymmetric Molecules 544
Sidebar - Chiral Recognition 544
11.4 Optical Isomerism 546
11.5 Fisher Projections 549
11.6 Molecules with Two Stereocenters 553
11.7 Resolution of Enantiomers 558
11.8 Stereocenters Other than Carbon 561
Key Ideas from Chapter 11 564
Chapter 12
Aliphatic Nucleophilic Substitution
12.1 Naming Single Bonded Heteroatom Functional
Groups 579
12.2 Comparing Nucleophilic Substitution Reaction
Mechanisms 586
12.3 The SN1 and SN2 Reaction Mechanisms 588
12.4 Stereochemistry of Nucleophilic Substitutions 592
12.5 The Substrate 595
12.6 Nucleophiles and Leaving Groups 601
12.7 Common Nucleophiles 606
12.8 The Reaction Medium 607
12.9 SN1 versus SN2 613
12.10 Halide Nucleophiles 613
Synthesis of 1-Bromobutane 616
12.11 Oxygen Nucleophiles 620
12.12 Nitrogen Nucleophiles 625
Synthesis of 2,5-Diaminoadipic Acid 628
12.13 Carbon Nucleophiles 631
12.14 Neighboring Group Participation 634
Special Topic - SN1 vs. SN2 637
Key Ideas from Chapter 12 641
Chapter 13
Elimination Reactions
13.1 The Elimination Mechanisms 658
13.2 Stereochemistry of Eliminations 660
13.3 Direction of Elimination 663
13.4 E1 vs. E2 670
13.5 Elimination vs. Substitution 671
13.6 Summary of Elimination and Substitution 673
13.7 E & Z Nomenclature 677
13.8 Elimination of Organohalogens 678
13.9 Dehydration of Alcohols 682
Synthesis of Cyclohexene 685
13.10 Pinacol Rearrangement 686
13.11 Hofmann Elimination 691
13.12 Oxidation of Alcohols 694
Synthesis of Citronellal 697
Key Ideas from Chapter 13 698
Chapter 14
Electrophilic Addition to
Unsaturated Carbons
14.1 Addition Reaction Mechanisms 713
14.2 Direction and Stereochemistry of Addition
Reactions 715
14.3 Addition of Hydrogen Halides 718
14.4 Addition of Water and Alcohols 722
14.5 Hydroboration-Oxidation 726
Synthesis of (-)-Isopinocampheol 730
14.6 Electrophilic Addition of Halogens 732
14.7 Addition of Hydrogen 736
14.8 Dihydroxylation Reactions 742
14.9 Addition of Carbenes 745
Synthesis of 7,7-Dichlorobicyclo[4.1.0]heptane 749
14.10 Oxidation of Alkenes 750
Key Ideas from Chapter 14 754
Chapter 15
Organic Synthesis
15.1 Synthesis Design and Strategy 771
15.2 Principles of Retrosynthetic Analysis 774
15.3 Protecting Groups 778
Synthesis of the Ethylene Glycol Acetal of
Cyclohexanone 781
15.4 Lithium Dialkylcuprate Reagents 781
Synthesis of trans-Stilbene 784
15.5 A Synthetic Example 786
15.6 Synthesis of Difunctional Compounds 790
Key Ideas from Chapter 15 795
Chapter 16
Conjugation and Resonance
16.1 Naming Compounds with Multiple Functional
Groups 812
16.2 Conjugated Dienes 816
16.3 The Allyl Group and Resonance 823
16.4 Conjugate Addition Reactions 826
Special Topic - Ultraviolet Spectroscopy 829
16.5 Double Bonds Conjugated With Carbonyl
Groups 832
Sidebar - The Chemistry of Vision 834
16.6 The Diels-Alder Reaction 837
Synthesis of cis-Norbornene-5,6-endo-dicarboxylic
Anhydride 841
16.7 Orbital Symmetry and the Diels-Alder
Reaction 844
16.8 Synthesis with the Diels-Alder Reaction 847
Key Ideas from Chapter 16 852
Chapter 17
Aromaticity
17.1 Benzene 868
Sidebar - Diamond, Graphite, and Buckyballs 872
17.2 The Stability of Benzene 874
17.3 Molecular Orbitals in Benzene 876
17.4 The Molecular Orbitals of Cyclobutadiene 879
17.5 Aromaticity 880
17.6 Hückel’s Rule 882
17.7 Aromatic Ions 887
17.8 Naming Benzene Derivatives 891
17.9 Aromatic Heterocyclic Compounds 895
17.10 Polynuclear Aromatic Hydrocarbons 898
17.11 The Benzyl Group 900
Key Ideas from Chapter 17 901
Chapter 18
Aromatic Substitution Reactions
18.1 Mechanism of Aromatic Electrophilic Substitution 914
18.2 The Nitration of Benzene 917
18.3 Halogenation and Sulfonation of Benzene 920
18.4 Friedel-Crafts Alkylation and Acylation 924
18.5 Effects of Monosubstituted Arenes on Substitution 928
18.6 Rate Effects with Monosubstituted Arenes 932
18.7 Classification of Substituents 935
18.8 Friedel-Crafts Acylation 943
Synthesis of o-Benzoylbenzoic Acid 947
18.9 Multiple Substituent Effects 948
18.10 Substitution on Polycyclic Arenes 951
18.11 Diazotization 954
Synthesis of Methyl Orange 957
Sidebar - Sulfa Drugs 958
18.12 Other Diazonium Salt Reactions 961
18.13 Nucleophilic Aromatic Substitution 963
18.14 Benzyne 965
Synthesis of Trypticene 968
18.15 Synthesis Examples 969
Key Ideas from Chapter 18 975
Chapter 19
a Substitution on Carbonyl Compounds
19.1 Keto-Enol Tautomerism 997
19.2 Enols and Enolate Ions 999
19.3 The Mechanism of a Substitution 1002
19.4 a Halogenations 1003
Synthesis of 2-Bromocholestanone 1005
19.5 Alkylation of Enolate Ions 1009
19.6 Stabilized Enolate Ions 1012
Sidebar - Barbiturates 1020
19.7 Enamine Reaction 1023
Synthesis of 2-Acetylcyclohexanone 1026
19.8 Silyl Enol Ethers 1027
19.9 1,3-Dithianes 1030
Key Ideas from Chapter 19 1033
Chapter 20
Carbonyl Condensation Reactions
20.1 The Carbonyl Condensation Mechanism 1052
20.2 Carbonyl Condensation Vs a Substitution 1054
Sidebar - Borodin and Aldehydes 1056
20.3 Mixed Aldol Condensations 1057
20.4 Intramolecular Aldol Condensations 1061
Synthesis of 1,5-Diphenyl-1,4-pentadien-3-one 1063
20.5 The Claisen Condensation 1064
Sidebar - Biochemical Carbonyl Condensation Reactions 1067
20.6 The Dieckmann Cyclization 1071
20.7 The Michael Addition Reaction 1072
20.8 The Robinson Annulation Reaction 1076
Synthesis of 4,4-Dimethyl-2-cyclohexen-2-one 1079
20.9 Carbonyl Condensations in Synthesis 1080
Key Ideas from Chapter 20 1084
Chapter 21
Radical Reactions
21.1 Radical Structure and Stability 1093
21.2 Halogenation of Alkanes 1095
Sidebar - Atmospheric Ozone Depletion 1099
21.3 Allylic Bromination 1102
21.4 Benzylic Bromination 1105
Synthesis of 1-Bromo-1-phenylethane 1106
21.5 Radical Addition to Alkenes 1107
21.6 Radical Oxidations 1112
21.7 Radical Reductions 1115
Synthesis of 1-Methoxy-1,4-cyclohexadiene 1121
Special Topic - Electron Spin Resonance Spectroscopy 1122
Key Ideas from Chapter 21 1125
Chapter 22
Polymer Chemistry
22.1 Structural Characteristics of Polymers 1138
22.2 Polymer Nomenclature 1141
22.3 Types of Polymerization Reactions 1144
22.4 Chain-Growth Polymerization 1146
Synthesis of Poly(vinyl acetate) 1155
Sidebar - Natural Rubber 1155
22.5 Controlling Stereochemistry in Vinyl Polymers 1157
22.6 Nonvinyl Chain-Growth Polymerization 1160
22.7 Step-Growth Polymerization 1163
Synthesis of Poly(ethylene terephthalate) 1165
Sidebar - Plastic Recycling 1167
22.8 Copolymers 1169
Sidebar - Plasticizers 1172
22.9 Cross-Linked Polymers 1173
Key Ideas from Chapter 22 1178
Chapter 24
Carbohydrates
24.1 Classification of Carbohydrates 1250
24.2 Monosaccharides 1253
24.3 Cyclic Forms of Monosaccharides 1256
Sidebar - The Sweet Taste 1260
24.4 Reactions of Monosaccharides 1263
24.5 Oxidation and Reduction Reactions 1265
24.6 Changing the Chain Length 1268
24.7 Fischer Proof of Glucose Structure 1271
24.8 Glycolysis - I 1275
24.9 Glycolysis - II 1280
Sidebar - Arsenic Poisoning 1285
24.10 Glycoside Formation 1286
24.11 Disaccharides 1291
24.12 Polysaccharides 1291
Key Ideas from Chapter 24 1294
Chapter 25
Nucleic Acids
25.1 Nucleosides and Nucleotides 1306
25.2 Laboratory Synthesis of Nucleotides and Nucleosides 1310
25.3 Nucleic Acids 1314
25.4 Replication of DNA 1317
Sidebar - The Polymerase Chain Reaction 1321
25.5 Structure and Biosynthesis of RNA 1325
25.6 RNA and Peptide Biosynthesis 1328
25.7 Sequencing of DNA 1332
25.8 Laboratory Nucleic Acid Synthesis 1337
Sidebar - Self Replicating Organic Compounds 1343
Key Ideas from Chapter 25 1345
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