Cover Page: iii
Preface Page: xvii
About This Book Page: xvii
To the Student of Organic Chemistry Page: xviii
To the Instructor Page: xxi
About the Companion Website Page: xxiii
1 Bonding and Structure of Organic Compounds Page: 1
1.1 Introduction Page: 1
1.2 Electronic Structure of Atoms Page: 4
1.3 Chemical Bonds Page: 9
1.4 Chemical Formulas Page: 18
1.5 The Covalent Bond Page: 20
1.6 Bonding – Concept Summary and Applications Page: 28
1.7 Intermolecular Attractions Page: 29
1.8 Intermolecular Molecular Interactions – Concept Summary and Applications Page: 31
End of Chapter Problems Page: 34
2 Carbon Functional Groups and Organic Nomenclature Page: 39
2.1 Introduction Page: 39
2.2 Functional Groups Page: 39
2.3 Saturated Hydrocarbons Page: 41
2.4 Organic Nomenclature Page: 45
2.5 Structure and Nomenclature of Alkanes Page: 45
2.6 Unsaturated Hydrocarbons Page: 54
2.7 Structure and Nomenclature of Alkenes Page: 56
2.8 Structure and Nomenclature of Substituted Benzenes Page: 58
2.9 Structure and Nomenclature of Alkynes Page: 60
End of Chapter Problems Page: 61
3 Heteroatomic Functional Groups and Organic Nomenclature Page: 63
3.1 Properties and Structure of Alcohols, Phenols, and Thiols Page: 63
3.2 Nomenclature of Alcohols Page: 66
3.3 Nomenclature of Thiols Page: 68
3.4 Structure and Properties of Aldehydes and Ketones Page: 69
3.5 Nomenclature of Aldehydes Page: 70
3.6 Nomenclature of Ketones Page: 71
3.7 Structure and Properties of Carboxylic Acids Page: 73
3.8 Nomenclature of Carboxylic Acids Page: 75
3.9 Structure and Properties of Esters Page: 78
3.10 Structure and Properties of Acid Chlorides Page: 82
3.11 Structure and Properties of Anhydrides Page: 83
3.12 Structure and Properties of Amines Page: 84
3.13 Structure and Properties of Amides Page: 88
3.14 Structure and Properties of Nitriles Page: 90
3.15 Structure and Properties of Ethers Page: 91
3.16 An Overview of Spectroscopy and the Relationship to Functional Groups Page: 94
End of Chapter Problems Page: 99
4 Alkanes, Cycloalkanes, and Alkenes: Isomers, Conformations, and Stabilities Page: 103
4.1 Introduction Page: 103
4.2 Structural Isomers Page: 103
4.3 Conformational Isomers of Alkanes Page: 104
4.4 Conformational Isomers of Cycloalkanes Page: 108
4.5 Geometric Isomers Page: 114
4.6 Stability of Alkanes Page: 119
4.7 Stability of Alkenes Page: 121
4.8 Stability of Alkynes Page: 122
End of Chapter Problems Page: 123
5 Stereochemistry Page: 125
5.1 Introduction Page: 125
5.2 Chiral Stereoisomers Page: 126
5.3 Significance of Chirality Page: 129
5.4 Nomenclature of the Absolute Configuration of Chiral Molecules Page: 131
5.5 Properties of Stereogenic Compounds Page: 133
5.6 Compounds with More Than One Stereogenic Carbon Page: 134
5.7 Resolution of Enantiomers Page: 137
End of Chapter Problems Page: 140
6 An Overview of the Reactions of Organic Chemistry Page: 145
6.1 Introduction Page: 145
6.2 Acid–Base Reactions Page: 145
6.3 Addition Reactions Page: 149
6.4 Reduction Reactions Page: 150
6.5 Oxidation Reactions Page: 153
6.6 Elimination Reactions Page: 154
6.7 Substitution Reactions Page: 156
6.8 Pericyclic Reactions Page: 158
6.9 Catalytic Coupling Reactions Page: 158
End of Chapter Problems Page: 159
7 Acid–Base Reactions in Organic Chemistry Page: 165
7.1 Introduction Page: 165
7.2 Lewis Acids and Bases Page: 165
7.3 Relative Strengths of Acids and Conjugate Bases Page: 166
7.4 Predicting the Relative Strengths of Acids and Bases Page: 169
7.5 Factors That Affect Acid and Base Strengths Page: 170
7.6 Applications of Acid–Bases Reactions in Organic Chemistry Page: 176
End of Chapter Problems Page: 180
8 Addition Reactions Involving Alkenes and Alkynes Page: 183
8.1 Introduction Page: 183
8.2 The Mechanism for Addition Reactions Involving Alkenes Page: 183
8.3 Addition of Hydrogen Halide to Alkenes (Hydrohalogenation of Alkenes) Page: 185
8.4 Addition of Halogens to Alkenes (Halogenation of Alkenes) Page: 196
8.5 Addition of Halogens and Water to Alkenes (Halohydrin Formation) Page: 198
8.6 Addition of Water to Alkenes (Hydration of Alkenes) Page: 199
8.7 Addition of Carbenes to Alkenes Page: 207
8.8 The Mechanism for Addition Reactions Involving Alkynes Page: 209
8.9 Applications of Addition Reactions to Synthesis Page: 213
End of Chapter Problems Page: 214
9 Addition Reactions Involving Carbonyls and Nitriles Page: 223
9.1 Introduction Page: 223
9.2 Mechanism for Addition Reactions Involving Carbonyl Compounds Page: 223
9.3 Addition of HCN to Carbonyl Compounds Page: 224
9.4 Addition of Water to Carbonyl Compounds Page: 226
9.5 Addition of Alcohols to Carbonyl Compounds Page: 230
9.6 Addition of Ylides to Carbonyl Compounds (The Wittig Reaction) Page: 235
9.7 Addition of Enolates to Carbonyl Compounds Page: 237
9.8 Addition of Amines to Carbonyl Compounds Page: 240
9.9 Mechanism for Addition Reactions Involving Imines Page: 241
9.10 Mechanism for Addition Reactions Involving Nitriles Page: 242
9.11 Applications of Addition Reactions to Synthesis Page: 244
End of Chapter Problems Page: 246
10 Reduction Reactions in Organic Chemistry Page: 251
10.1 Introduction Page: 251
10.2 Reducing Agents of Organic Chemistry Page: 252
10.3 Reduction of C=O and C=S Containing Compounds Page: 255
10.4 Reduction of Imines Page: 263
10.5 Reduction of Oxiranes Page: 266
10.6 Reduction of Aromatic Compounds, Alkynes, and Alkenes Page: 268
End of Chapter Problems Page: 272
11 Oxidation Reactions in Organic Chemistry Page: 275
11.1 Introduction Page: 275
11.2 Oxidation Page: 275
11.3 Oxidation of Alcohols and Aldehydes Page: 279
11.4 Oxidation of Alkenes Without Bond Cleavage Page: 288
11.5 Oxidation of Alkenes with Bond Cleavage Page: 293
11.6 Applications of Oxidation Reactions of Alkenes Page: 296
11.7 Oxidation of Alkynes Page: 299
11.8 Oxidation of Aromatic Compounds Page: 300
11.9 Autooxidation of Ethers and Alkenes Page: 301
11.10 Applications of Oxidation Reactions to Synthesis Page: 302
End of Chapter Problems Page: 304
12 Elimination Reactions of Organic Chemistry Page: 309
12.1 Introduction Page: 309
12.2 Mechanisms of Elimination Reactions Page: 309
12.3 Elimination of Hydrogen and Halide (Dehydrohalogenation) Page: 316
12.4 Elimination of Water (Dehydration) Page: 319
12.5 Applications of Elimination Reactions to Synthesis Page: 323
End of Chapter Problems Page: 326
13 Spectroscopy Revisited, A More Detailed Examination Page: 331
13.1 Introduction Page: 331
13.2 The Electromagnetic Spectrum Page: 331
13.3 UV‐Vis Spectroscopy and Conjugated Systems Page: 334
13.4 Infrared Spectroscopy Page: 337
13.5 Mass Spectrometry Page: 343
13.6 Nuclear Magnetic Resonance (NMR) Spectroscopy Page: 346
End of Chapter Problems Page: 367
14 Free Radical Substitution Reactions Involving Alkanes Page: 369
14.1 Introduction Page: 369
14.2 Types of Alkanes and Alkyl Halides Page: 371
14.3 Chlorination of Alkanes Page: 376
14.4 Bromination of Alkanes Page: 380
14.5 Applications of Free Radical Substitution Reactions Page: 386
14.6 Free Radical Inhibitors Page: 388
14.7 Environmental Impact of Organohalides and Free Radicals Page: 389
End of Chapter Problems Page: 391
15 Nucleophilic Substitution Reactions at sp3 Carbons Page: 393
15.1 Introduction Page: 393
15.2 The Electrophile Page: 393
15.3 The Leaving Group Page: 394
15.4 The Nucleophile Page: 397
15.5 Nucleophilic Substitution Reactions Page: 397
15.6 Bimolecular Substitution Reaction Mechanism (SN2 Mechanism) Page: 400
15.7 Unimolecular Substitution Reaction Mechanism (SN1 Mechanism) Page: 406
15.8 Applications of Nucleophilic Substitution Reactions – Synthesis Page: 414
End of Chapter Problems Page: 420
16 Nucleophilic Substitution Reactions at Acyl Carbons Page: 425
16.1 Introduction Page: 425
16.2 Mechanism for Acyl Substitution Page: 426
16.3 Substitution Reactions Involving Acid Chlorides Page: 428
16.4 Substitution Reactions Involving Anhydrides Page: 436
16.5 Substitution Reactions Involving Esters Page: 442
16.6 Substitution Reactions Involving Amides Page: 451
16.7 Substitution Reactions Involving Carboxylic Acids Page: 454
16.8 Substitution Reactions Involving Oxalyl Chloride Page: 458
16.9 Substitution Reactions Involving Sulfur Containing Compounds Page: 458
16.10 Applications of Acyl Substitution Reactions Page: 460
End of Chapter Problems Page: 462
17 Aromaticity and Aromatic Substitution Reactions Page: 467
17.1 Introduction Page: 467
17.2 Structure and Properties of Benzene Page: 468
17.3 Nomenclature of Substituted Benzene Page: 470
17.4 Stability of Benzene Page: 473
17.5 Characteristics of Aromatic Compounds Page: 475
17.6 Electrophilic Aromatic Substitution Reactions of Benzene Page: 478
17.7 Electrophilic Aromatic Substitution Reactions of Substituted Benzene Page: 484
17.8 Applications – Synthesis of Substituted Benzene Compounds Page: 491
17.9 Electrophilic Substitution Reactions of Polycyclic Aromatic Compounds Page: 494
17.10 Electrophilic Substitution Reactions of Pyrrole Page: 496
17.11 Electrophilic Substitution Reactions of Pyridine Page: 497
17.12 Nucleophilic Aromatic Substitution Page: 499
End of Chapter Problems Page: 504
18 Conjugated Systems and Pericyclic Reactions Page: 511
18.1 Conjugated Systems Page: 511
18.2 Pericyclic Reactions Page: 513
End of Chapter Problems Page: 522
19 Catalytic Carbon–Carbon Coupling Reactions Page: 525
19.1 Introduction Page: 525
19.2 Reactions of Transition Metal Complexes Page: 525
19.3 Palladium‐Catalyzed Coupling Reactions Page: 528
End of Chapter Problems Page: 535
20 Synthetic Polymers and Biopolymers Page: 537
20.1 Introduction Page: 537
20.2 Cationic Polymerization of Alkenes Page: 537
20.3 Anionic Polymerization of Alkenes Page: 540
20.4 Free Radical Polymerization of Alkenes Page: 540
20.5 Copolymerization of Alkenes Page: 542
20.6 Properties of Polymers Page: 543
20.7 Biopolymers Page: 544
20.8 Amino Acids, Monomers of Peptides and Proteins Page: 545
20.9 Acid–Base Properties of Amino Acids Page: 547
20.10 Synthesis of α‐Amino Acids Page: 547
20.11 Reactions of α‐Amino Acids Page: 550
20.12 Primary Structure and Properties of Peptides Page: 556
20.13 Secondary Structure of Proteins Page: 558
20.14 Monosaccharides, Monomers of Carbohydrates Page: 559
20.15 Reactions of Monosaccharides Page: 560
20.16 Disaccharides and Polysaccharides Page: 566
20.17 N‐Glycosides and Amino Sugars Page: 567
20.18 Lipids Page: 568
20.19 Properties and Reactions of Waxes Page: 569
20.20 Properties and Reactions of Triglycerides Page: 569
20.21 Properties and Reactions of Phospholipids Page: 572
20.22 Structure and Properties of Steroids, Prostaglandins, and Terpenes Page: 572
End of Chapter Problems Page: 573
Index Page: 577
End User License Agreement Page: 595
Provides an in-depth study of organic compounds that bridges the gap between general and organic chemistry
Organic Chemistry: Concepts and Applications presents a comprehensive review of organic compounds that is appropriate for a two-semester sophomore organic chemistry course. The text covers the fundamental concepts needed to understand organic chemistry and clearly shows how to apply the concepts of organic chemistry to problem-solving. In addition, the book highlights the relevance of organic chemistry to the environment, industry, and biological and medical sciences. The author includes multiple-choice questions similar to aptitude exams for professional schools, including the Medical College Admissions Test (MCAT) and Dental Aptitude Test (DAT) to help in the preparation for these important exams.
Rather than categorize content information by functional groups, which often stresses memorization, this textbook instead divides the information into reaction types. This approach bridges the gap between general and organic chemistry and helps students develop a better understanding of the material. A manual of possible solutions for chapter problems for instructors and students is available in the supplementary websites. This important book:
• Provides an in-depth study of organic compounds with division by reaction types that bridges the gap between general and organic chemistry
• Covers the concepts needed to understand organic chemistry and teaches how to apply them for problem-solving
• Puts a focus on the relevance of organic chemistry to the environment, industry, and biological and medical sciences
• Includes multiple choice questions similar to aptitude exams for professional schools
Written for students of organic chemistry, Organic Chemistry: Concepts and Applications is the comprehensive text that presents the material in clear terms and shows how to apply the concepts to problem solving.
