Organic Chemistry: Concepts and Applications

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.

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