1 A Review of General Chemistry: Electrons, Bonds, and Molecular Properties 1 1.1 Introduction to Organic Chemistry 2 1.2 The Structural Theory of Matter 3 1.3 Electrons, Bonds, and Lewis Structures 4 1.4 Identifying Formal Charges 7 1.5 Induction and Polar Covalent Bonds 8 1.6 Reading Bond- Line Structures 11 1.7 Atomic Orbitals 14 1.8 Valence Bond Theory 17 1.9 Molecular Orbital Theory 18 1.10 Hybridized Atomic Orbitals 20 1.11 Predicting Molecular Geometry: VSEPR Theory 26 1.12 Dipole Moments and Molecular Polarity 30 1.13 Intermolecular Forces and Physical Properties 33 WorldLinks Biomimicry and Gecko Feet 37 BioLinks Drug- Receptor Interactions 38 1.14 Solubility 39 BioLinks Propofol: The Importance of Drug Solubility 40 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems 2 Molecular Representations 49 2.1 Molecular Representations 50 2.2 Bond- Line Structures 52 2.3 Identifying Functional Groups 54 BioLinks Marine Natural Products 55 2.4 Carbon Atoms with Formal Charges 57 2.5 Identifying Lone Pairs 57 2.6 Three- Dimensional Bond- Line Structures 60 BioLinks The Opioids 61 2.7 Introduction to Resonance 62 2.8 Curved Arrows 64 2.9 Formal Charges in Resonance Structures 66 2.10 Drawing Resonance Structures via Pattern Recognition 68 2.11 Assessing the Relative Importance of Resonance Structures 73 2.12 The Resonance Hybrid 77 2.13 Delocalized and Localized Lone Pairs 79 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems 3 Acids and Bases 91 3.1 Introduction to Brønsted- Lowry Acids and Bases 92 3.2 Flow of Electron Density: Curved- Arrow Notation 92 BioLinks Antacids and Heartburn 94 3.3 Brønsted- Lowry Acidity: Quantitative Perspective 95 BioLinks Drug Distribution and pK a 101 3.4 Brønsted- Lowry Acidity: Qualitative Perspective 102 3.5 Brønsted- Lowry Acidity: Assessing the Relative Acidity of Cationic Acids 113 3.6 Position of Equilibrium and Choice of Reagents 118 3.7 Leveling Effect 121 3.8 Solvating Effects 122 3.9 Counterions 123 WorldLinks Baking Soda versus Baking Powder 123 3.10 Lewis Acids and Bases 124 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems 4 Alkanes and Cycloalkanes 137 4.1 Introduction to Alkanes 138 4.2 Nomenclature of Alkanes 138 WorldLinks Pheromones: Chemical Messengers 142 BioLinks Naming Drugs 150 4.3 Constitutional Isomers of Alkanes 151 4.4 Relative Stability of Isomeric Alkanes 152 4.5 Sources and Uses of Alkanes 153 WorldLinks An Introduction to Polymers 155 4.6 Drawing Newman Projections 155 4.7 Conformational Analysis of Ethane and Propane 157 4.8 Conformational Analysis of Butane 159 BioLinks Drugs and Their Conformations 163 4.9 Cycloalkanes 163 BioLinks Cyclopropane as an Inhalation Anesthetic 165 4.10 Conformations of Cyclohexane 166 4.11 Drawing Chair Conformations 167 4.12 Monosubstituted Cyclohexane 169 4.13 Disubstituted Cyclohexane 171 4.14 cis-trans Stereoisomerism 175 4.15 Polycyclic Systems 176 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems 5 Stereoisomerism 187 5.1 Overview of Isomerism 188 5.2 Introduction to Stereoisomerism 189 WorldLinks The Sense of Smell 194 5.3 Designating Configuration Using the Cahn-Ingold-Prelog System 194 BioLinks Chiral Drugs 199 5.4 Optical Activity 200 5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers 206 5.6 Symmetry and Chirality 209 5.7 Fischer Projections 213 5.8 Conformationally Mobile Systems 215 5.9 Chirality without a Chiral Center 216 5.10 Resolution of Racemic Mixtures 217 5.11 Asymmetric Synthesis: Stereoselective and Stereospecific Reactions 219 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems 6 Chemical Reactivity and Mechanisms 229 6.1 Enthalpy 230 6.2 Entropy 233 6.3 Gibbs Free Energy 235 WorldLinks Explosives 236 WorldLinks Do Living Organisms Violate the Second Law of Thermodynamics? 238 6.4 Equilibria 238 6.5 Kinetics 240 BioLinks Nitroglycerin: An Explosive with Medicinal Properties 243 WorldLinks Beer Making 244 6.6 Energy Diagrams 245 6.7 Nucleophiles and Electrophiles 248 6.8 Mechanisms and Arrow Pushing 252 6.9 Combining the Patterns of Arrow Pushing 257 6.10 Drawing Curved Arrows 259 6.11 Carbocation Rearrangements 262 6.12 Reversible and Irreversible Reaction Arrows 264 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems 7 Substitution Reactions 277 7.1 Introduction to Substitution Reactions 278 7.2 Alkyl Halides 279 7.3 Possible Mechanisms for Substitution Reactions 283 7.4 The S N 2 Mechanism 285 BioLinks Pharmacology and Drug Design 291 7.5 Nucleophilic Strength in S N 2 Reactions 293 BioLinks S N 2 Reactions in Biological Systems—Methylation 293 7.6 The S N 1 Mechanism 295 7.7 Solvent Effects in Substitution Reactions 301 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems • Integrated Problems Challenge Problems 8 Alkenes: Structure and Preparation via Elimination Reactions 313 8.1 Introduction to Elimination Reactions 314 8.2 Stereoisomerism in Alkenes 314 BioLinks Phototherapy Treatment for Neonatal Jaundice 317 8.3 Stability of Alkenes and Cycloalkenes 319 8.4 Possible Mechanisms for Elimination Reactions 321 8.5 The E2 Mechanism 323 8.6 Regiochemical and Stereochemical Outcomes for E2 Reactions 325 8.7 The E1 Mechanism 335 8.8 Predicting Products: Substitution vs. Elimination 342 8.9 Substitution and Elimination Reactions with Other Substrates 348 8.10 Synthesis Strategies – Substitution and Elimination 352 BioLinks Radiolabeled Compounds in Diagnostic Medicine 356 SpecialTopic Kinetic Isotope Effects 361 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 9 Addition Reactions of Alkenes 371 9.1 Introduction to Addition Reactions 372 9.2 Alkenes in Nature and in Industry 373 WorldLinks Pheromones to Control Insect Populations 373 9.3 Nomenclature of Alkenes 374 9.4 Addition vs. Elimination: A Thermodynamic Perspective 376 9.5 Hydrohalogenation 377 WorldLinks Cationic Polymerization and Polystyrene 384 9.6 Acid-Catalyzed Hydration 385 9.7 Oxymercuration-Demercuration 389 9.8 Hydroboration-Oxidation 390 9.9 Catalytic Hydrogenation 396 WorldLinks Partially Hydrogenated Fats and Oils 401 9.10 Halogenation and Halohydrin Formation 402 9.11 Anti Dihydroxylation 406 9.12 Syn Dihydroxylation 409 9.13 Oxidative Cleavage 411 9.14 Predicting the Products of an Addition Reaction 413 9.15 Synthesis Strategies 415 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 10 Alkynes 431 10.1 Introduction to Alkynes 432 BioLinks The Role of Molecular Rigidity 434 WorldLinks Conducting Organic Polymers 435 10.2 Nomenclature of Alkynes 435 10.3 Acidity of Acetylene and Terminal Alkynes 437 10.4 Preparation of Alkynes 440 10.5 Reduction of Alkynes 442 10.6 Hydrohalogenation of Alkynes 445 10.7 Hydration of Alkynes 447 10.8 Halogenation of Alkynes 453 10.9 Ozonolysis of Alkynes 453 10.10 Alkylation of Terminal Alkynes 454 10.11 Synthesis Strategies 456 Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 11 Radical Reactions 467 11.1 Radicals 468 11.2 Common Patterns in Radical Mechanisms 473 11.3 Chlorination of Methane 476 11.4 Thermodynamic Considerations for Halogenation Reactions 480 11.5 Selectivity of Halogenation 482 11.6 Stereochemistry of Halogenation 485 11.7 Allylic Bromination 487 11.8 Atmospheric Chemistry and the Ozone Layer 490 WorldLinks Fighting Fires with Chemicals 492 11.9 Autooxidation and Antioxidants 493 BioLinks Why Is an Overdose of Acetaminophen Fatal? 495 11.10 Radical Addition of HBr: Anti-Markovnikov Addition 496 11.11 Radical Polymerization 500 11.12 Radical Processes in the Petrochemical Industry 502 11.13 Halogenation as a Synthetic Technique 502 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 12 Systematic Approach to Synthesis 511 12.1 One-Step Syntheses 512 12.2 Functional Group Transformations 513 12.3 Reactions That Change the Carbon Skeleton 517 BioLinks Vitamins 519 12.4 How to Approach a Synthesis Problem 520 BioLinks The Total Synthesis of Vitamin B 12 524 12.5 Multi- Step Synthesis and Retrosynthetic Analysis 526 WorldLinks Retrosynthetic Analysis 531 12.6 Green Chemistry 531 12.7 Practical Tips for Increasing Proficiency 532 BioLinks Total Synthesis of Taxol 533 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems Review of Reactions • 13 Alcohols and Phenols 541 13.1 Structure and Properties of Alcohols 542 BioLinks Chain Length as a Factor in Drug Design 546 13.2 Acidity of Alcohols and Phenols 547 13.3 Preparation of Alcohols via Substitution or Addition 550 13.4 Preparation of Alcohols via Reduction 551 13.5 Preparation of Diols 558 WorldLinks Antifreeze 559 13.6 Preparation of Alcohols via Grignard Reagents 559 13.7 Protection of Alcohols 564 13.8 Preparation of Phenols 565 13.9 Reactions of Alcohols: Substitution and Elimination 566 BioLinks Drug Metabolism 569 13.10 Reactions of Alcohols: Oxidation 571 13.11 Biological Redox Reactions 575 BioLinks Biological Oxidation of Methanol and Ethanol 577 13.12 Oxidation of Phenol 577 13.13 Synthesis Strategies 579 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 14 Ethers and Epoxides; Thiols and Sulfides 597 14.1 Introduction to Ethers 598 14.2 Nomenclature of Ethers 598 14.3 Structure and Properties of Ethers 600 BioLinks Ethers as Inhalation Anesthetics 601 14.4 Crown Ethers 602 WorldLinks Chelating Agents in the Food Industry and in Medicine 604 14.5 Preparation of Ethers 605 14.6 Reactions of Ethers 608 14.7 Nomenclature of Epoxides 611 BioLinks Epothilones as Novel Anticancer Agents 612 14.8 Preparation of Epoxides 612 BioLinks Active Metabolites and Drug Interactions 615 14.9 Enantioselective Epoxidation 615 14.10 Ring- Opening Reactions of Epoxides 617 WorldLinks Ethylene Oxide as a Sterilizing Agent for Sensitive Medical Equipment 620 BioLinks Cigarette Smoke and Carcinogenic Epoxides 624 14.11 Thiols and Sulfides 625 14.12 Synthesis Strategies Involving Epoxides 629 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 15 Infrared Spectroscopy and Mass Spectrometry 647 15.1 Introduction to Spectroscopy 648 WorldLinks Microwave Ovens 650 15.2 IR Spectroscopy 650 BioLinks IR Thermal Imaging for Cancer Detection 651 15.3 Signal Characteristics: Wavenumber 652 15.4 Signal Characteristics: Intensity 657 WorldLinks IR Spectroscopy for Testing Blood Alcohol Levels 659 15.5 Signal Characteristics: Shape 659 15.6 Analyzing an IR Spectrum 663 15.7 Using IR Spectroscopy to Distinguish between Two Compounds 668 15.8 Introduction to Mass Spectrometry 669 WorldLinks Mass Spectrometry for Detecting Explosives 671 15.9 Analyzing the (M) +• Peak 672 15.10 Analyzing the (M+1) +• Peak 673 15.11 Analyzing the (M+2) +• Peak 675 15.12 Analyzing the Fragments 677 15.13 High- Resolution Mass Spectrometry 680 15.14 Gas Chromatography– Mass Spectrometry 682 15.15 Liquid Chromatography–Mass Spectrometry 682 15.16 Mass Spectrometry of Large Biomolecules 683 WorldLinks Medical Applications of Mass Spectrometry 683 15.17 Hydrogen Deficiency Index: Degrees of Unsaturation 684 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems 16 Nuclear Magnetic Resonance Spectroscopy 695 16.1 Introduction to NMR Spectroscopy 696 16.2 Acquiring a 1 H NMR Spectrum 698 16.3 Characteristics of a 1 H NMR Spectrum 699 16.4 Number of Signals 700 16.5 Chemical Shift 706 16.6 Integration 713 16.7 Multiplicity 716 16.8 Drawing the Expected 1 H NMR Spectrum of a Compound 724 16.9 Using 1 H NMR Spectroscopy to Distinguish between Compounds 726 BioLinks Detection of Impurities in Heparin Sodium Using 1 H NMR Spectroscopy 728 16.10 Analyzing a 1 H NMR Spectrum 729 16.11 Acquiring a 13 C NMR Spectrum 732 16.12 Chemical Shifts in 13 C NMR Spectroscopy 732 16.13 DEPT 13 C NMR Spectroscopy 735 BioLinks Magnetic Resonance Imaging (MRI) 738 Review of Concepts and Vocabulary • SkillBuilder Review Practice Problems • Integrated Problems • Challenge Problems 17 Conjugated Pi Systems and Pericyclic Reactions 749 17.1 Classes of Dienes 750 17.2 Conjugated Dienes 751 17.3 Molecular Orbital Theory 753 17.4 Electrophilic Addition 757 17.5 Thermodynamic Control vs. Kinetic Control 760 WorldLinks Natural and Synthetic Rubbers 763 17.6 An Introduction to Pericyclic Reactions 764 17.7 Diels–Alder Reactions 765 17.8 MO Description of Cycloadditions 771 17.9 Electrocyclic Reactions 774 17.10 Sigmatropic Rearrangements 779 BioLinks The Photoinduced Biosynthesis of Vitamin D 781 17.11 Other Pericyclic Reactions 782 17.12 UV-Vis Spectroscopy 784 WorldLinks Sunscreens 788 17.13 Photoreductions and Photorearrangements 788 17.14 Color 792 WorldLinks Bleach 792 17.15 Chemistry of Vision 793 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 18 Aromatic Compounds 803 18.1 Introduction to Aromatic Compounds 804 WorldLinks What Is Coal? 805 18.2 Nomenclature of Benzene Derivatives 805 18.3 Structure of Benzene 808 18.4 Stability of Benzene 809 WorldLinks Molecular Cages 813 18.5 Aromatic Compounds Other Than Benzene 816 BioLinks The Development of Nonsedating Antihistamines 821 18.6 Reactions at the Benzylic Position 823 18.7 Reduction of Benzene and Its Derivatives 828 18.8 Spectroscopy of Aromatic Compounds 830 WorldLinks Buckyballs and Nanotubes 833 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 19 Aromatic Substitution Reactions 843 19.1 Introduction to Electrophilic Aromatic Substitution 844 19.2 Halogenation 844 BioLinks Halogenation in Drug Design 847 19.3 Sulfonation 848 WorldLinks What Are Those Colors in Fruity Pebbles? 849 19.4 Nitration 850 BioLinks The Discovery of Prodrugs 851 19.5 Friedel–Crafts Alkylation 852 19.6 Friedel–Crafts Acylation 855 19.7 Activating Groups 856 19.8 Deactivating Groups 860 19.9 Halogens: The Exception 862 19.10 Determining the Directing Effects of a Substituent 863 19.11 Multiple Substituents 867 19.12 Synthesis Strategies 872 19.13 Nucleophilic Aromatic Substitution 878 19.14 Elimination-Addition 880 19.15 Identifying the Mechanism of an Aromatic Substitution Reaction 882 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 20 Aldehydes and Ketones 895 20.1 Introduction to Aldehydes and Ketones 896 20.2 Nomenclature 897 20.3 Preparation of Aldehydes and Ketones: A Review 899 20.4 Introduction to Nucleophilic Addition Reactions 900 20.5 Oxygen Nucleophiles 903 BioLinks Acetals as Prodrugs 909 20.6 Nitrogen Nucleophiles 911 WorldLinks Beta- Carotene and Vision 915 20.7 Hydrolysis of Acetals, Imines, and Enamines 919 BioLinks Prodrugs 922 20.8 Sulfur Nucleophiles 922 20.9 Hydrogen Nucleophiles 923 20.10 Carbon Nucleophiles 924 WorldLinks Organic Cyanide Compounds in Nature 927 20.11 Baeyer– Villiger Oxidation of Aldehydes and Ketones 933 20.12 Synthesis Strategies 935 20.13 Spectroscopic Analysis of Aldehydes and Ketones 938 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 21 Carboxylic Acids and Their Derivatives 951 21.1 Introduction to Carboxylic Acids 952 21.2 Nomenclature of Carboxylic Acids 952 21.3 Structure and Properties of Carboxylic Acids 954 21.4 Preparation of Carboxylic Acids 957 21.5 Reactions of Carboxylic Acids 958 21.6 Introduction to Carboxylic Acid Derivatives 959 BioLinks Sedatives 961 21.7 Reactivity of Carboxylic Acid Derivatives 963 21.8 Preparation and Reactions of Acid Chlorides 970 21.9 Preparation and Reactions of Acid Anhydrides 975 BioLinks How Does Aspirin Work? 977 21.10 Preparation of Esters 978 21.11 Reactions of Esters 979 WorldLinks How Soap Is Made 980 BioLinks Esters as Prodrugs 981 21.12 Preparation and Reactions of Amides 984 WorldLinks Polyesters and Polyamides 985 BioLinks Beta-Lactam Antibiotics 988 21.13 Preparation and Reactions of Nitriles 989 21.14 Synthesis Strategies 992 21.15 Spectroscopy of Carboxylic Acids and Their Derivatives 997 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 22 Alpha Carbon Chemistry: Enols and Enolates 1009 22.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates 1010 22.2 Alpha Halogenation of Enols and Enolates 1017 22.3 Aldol Reactions 1022 WorldLinks Muscle Power 1025 22.4 Claisen Condensations 1033 22.5 Alkylation of the Alpha Position 1035 22.6 Conjugate Addition Reactions 1044 BioLinks Glutathione Conjugation and Biochemical Michael Reactions 1046 22.7 Synthesis Strategies 1050 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 23 Amines 1067 23.1 Introduction to Amines 1068 BioLinks Drug Metabolism Studies 1069 23.2 Nomenclature of Amines 1069 23.3 Properties of Amines 1072 BioLinks Fortunate Side Effects 1073 WorldLinks Chemical Warfare Among Ants 1077 23.4 Preparation of Amines: A Review 1078 23.5 Preparation of Amines via Substitution Reactions 1079 23.6 Preparation of Amines via Reductive Amination 1082 23.7 Synthesis Strategies 1084 23.8 Acylation of Amines 1087 23.9 Hofmann Elimination 1088 23.10 Reactions of Amines with Nitrous Acid 1091 23.11 Reactions of Aryl Diazonium Ions 1093 23.12 Nitrogen Heterocycles 1097 BioLinks H 2 -Receptor Antagonists and the Development of Cimetidine 1098 23.13 Spectroscopy of Amines 1100 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 24 Introduction to Organometallic Compounds 1113 24.1 General Properties of Organometallic Compounds 1114 24.2 Organolithium and Organomagnesium Compounds 1115 24.3 Lithium Dialkyl Cuprates (Gilman Reagents) 1118 24.4 The Simmons–Smith Reaction and Carbenoids 1122 24.5 Stille Coupling 1125 24.6 Suzuki Coupling 1131 24.7 Negishi Coupling 1136 24.8 The Heck Reaction 1141 24.9 Sonogashira Coupling 1146 24.10 Hiyama Coupling 1151 24.11 Alkene Metathesis 1154 WorldLinks Improving Biodiesel via Alkene Metathesis 1159 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 25 Carbohydrates 1175 25.1 Introduction to Carbohydrates 1176 25.2 Classification of Monosaccharides 1176 25.3 Configuration of Aldoses 1179 25.4 Configuration of Ketoses 1180 25.5 Cyclic Structures of Monosaccharides 1182 25.6 Reactions of Monosaccharides 1189 25.7 Disaccharides 1196 BioLinks Lactose Intolerance 1199 WorldLinks Artificial Sweeteners 1200 25.8 Polysaccharides 1201 25.9 Amino Sugars 1202 25.10 N-Glycosides 1203 BioLinks Aminoglycoside Antibiotics 1204 BioLinks Erythromycin Biosynthesis 1208 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 26 Amino Acids, Peptides, and Proteins 1217 26.1 Introduction to Amino Acids, Peptides, and Proteins 1218 26.2 Structure and Properties of Amino Acids 1219 WorldLinks Nutrition and Sources of Amino Acids 1221 WorldLinks Forensic Chemistry and Fingerprint Detection 1225 26.3 Amino Acid Synthesis 1226 26.4 Structure of Peptides 1230 BioLinks Polypeptide Antibiotics 1235 26.5 Sequencing a Peptide 1236 26.6 Peptide Synthesis 1239 26.7 Protein Structure 1247 BioLinks Diseases Caused by Misfolded Proteins 1250 26.8 Protein Function 1250 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 27 Lipids 1261 27.1 Introduction to Lipids 1262 27.2 Waxes 1263 27.3 Triglycerides 1263 27.4 Reactions of Triglycerides 1267 WorldLinks Soaps Versus Synthetic Detergents 1271 27.5 Phospholipids 1275 BioLinks Polyether Antibiotics 1278 27.6 Steroids 1279 BioLinks Cholesterol and Heart Disease 1282 BioLinks Anabolic Steroids and Competitive Sports 1284 27.7 Prostaglandins 1285 BioLinks NSAIDs and COX-2 Inhibitors 1286 27.8 Terpenes 1287 Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems 28 Synthetic Polymers* 28.1 Introduction to Synthetic Polymers 28.2 Nomenclature of Synthetic Polymers 28.3 Copolymers 28.4 Polymer Classification by Reaction Type 28.5 Polymer Classification by Mode of Assembly 28.6 Polymer Classification by Structure 28.7 Polymer Classification by Properties WorldLinks Safety Glass and Car Windshields 28.8 Polymer Recycling Review of Reactions • Review of Concepts and Vocabulary SkillBuilder Review • Practice Problems Integrated Problems • Challenge Problems Appendix A: Nomenclature of Polyfunctional Compounds A1 Appendix B: Multiple Choice Questions A5 Glossary G1 Index I1 Selected Answers*

Organic Chemistry Organic Chemistry 4th edition provides a comprehensive, yet accessible treatment of all the essential organic chemistry concepts covered in a two-semester course. The textbook includes all the concepts covered in a typical organic chemistry textbook but is unique in its skill development approach to the subject. Presented with a skills-based approach that bridges the gap between organic chemistry theory and real-world practice, the book places special emphasis on developing the problem-solving skills through applied exercises and activities. Numerous hands-on activities and real-world examples are integrated throughout the text to help students understand both the “why” and the “how” behind organic chemistry. This international adapted edition offers new and updated content with improved presentation of all course material. The text adopts greater focus on retrosynthetic strategies for synthesis and skill-building. Some of the chapters include updates in nomenclature, structural presentation, mechanisms, kinetic data and recent developments in synthesis and applications. The book presents ample opportunity for practice and assessment with numerous practice problems, review questions, SkillBuilder activities, and up-to-date literature-based problems. This book and series is authorized for sale in Europe, Middle East, Africa, Asia, Australia and New Zealand only and may not be exported. The content is comprehensively adapted to international requirements and materially different from similar products for other markets including the authorized U.S. counterpart of this title.