- ホーム
- > 洋書
- > 英文書
- > Science / Mathematics
Full Description
Introduction to Organic Chemistry, 5th Edition provides an introduction to organic chemistry for students who require the fundamentals of organic chemistry as a requirement for their major. It is most suited for a one semester organic chemistry course. In an attempt to highlight the relevance of the material to students, the authors place a strong emphasis on showing the interrelationship between organic chemistry and other areas of science, particularly the biological and health sciences. The text illustrates the use of organic chemistry as a tool in these sciences; it also stresses the organic compounds, both natural and synthetic, that surround us in everyday life: in pharmaceuticals, plastics, fibers, agrochemicals, surface coatings, toiletry preparations and cosmetics, food additives, adhesives, and elastomers.
Contents
01 Covalent Bonding and Shapes of Molecules 11.1 How Do We Describe the Electronic Structure of Atoms? 21.2 What Is the Lewis Model of Bonding? 51.3 How Do We Predict Bond Angles and the Shapes of Molecules? 141.4 How Do We Predict If a Molecule Is Polar or Nonpolar? 181.5 What Is Resonance? 191.6 What Is the Orbital Overlap Model of Covalent Bonding? 221.7 What Are Functional Groups? 28Summary of Key Questions 32Quick Quiz 34Problems 35Looking Ahead 40Group Learning Activities 40CHEMICAL CONNECTIONS1A Buckyball: A New Form of Carbon 1702 Acids and Bases 412.1 What Are Arrhenius Acids and Bases? 422.2 What Are Bronsted?Lowry Acids and Bases? 432.3 How Do We Measure the Strength of an Acid or Base? 462.4 How Do We Determine the Position of Equilibrium in an Acid?Base Reaction? 482.5 What Are the Relationships between Acidity and Molecular Structure? 502.6 What Are Lewis Acids and Bases? 54Summary of Key Questions 57Quick Quiz 58Key Reactions 59Problems 59Looking Ahead 62Group Learning Activities 6203 Alkanes and Cycloalkanes 633.1 What Are Alkanes? 643.2 What Is Constitutional Isomerism in Alkanes? 663.3 How Do We Name Alkanes? 693.4 What Are Cycloalkanes? 733.5 What Is the IUPAC System of Nomenclature? 753.6 What Are the Conformations of Alkanes and Cycloalkanes? 763.7 What Is Cis?Trans Isomerism in Cycloalkanes? 833.8 What Are the Physical Properties of Alkanes and Cycloalkanes? 873.9 What Are the Characteristic Reactions of Alkanes? 913.10 What Are the Sources of Alkanes? 91Summary of Key Questions 94Quick Quiz 96Key Reactions 97Problems 97Looking Ahead 102Group Learning Activities 104Putting It Together 104CHEMICAL CONNECTIONS3A The Poisonous Puffer Fish 843B Octane Rating: What Those Numbers at the Pump Mean 9404 Alkenes and Alkynes 1084.1 What Are the Structures and Shapes of Alkenes and Alkynes? 1104.2 How Do We Name Alkenes and Alkynes? 1124.3 What Are the Physical Properties of Alkenes and Alkynes? 1204.4 Why Are 1-Alkynes (Terminal Alkynes) Weak Acids? 122Summary of Key Questions 123Quick Quiz 124Problems 124Looking Ahead 128Group Learning Activities 128CHEMICAL CONNECTIONS4A Ethylene, a Plant Growth Regulator 1094B Cis?Trans Isomerism in Vision 1114C Why Plants Emit Isoprene 12105 Reactions of Alkenes and Alkynes 1295.1 What Are the Characteristic Reactions of Alkenes? 1305.2 What Is a Reaction Mechanism? 1305.3 What Are the Mechanisms of Electrophilic Additions to Alkenes? 1365.4 What Are Carbocation Rearrangements? 1475.5 What Is Hydroboration?Oxidation of an Alkene? 1505.6 How Can an Alkene Be Reduced to an Alkane? 1535.7 How Can an Acetylide Anion Be Used to Create a New Carbon?Carbon Bond? 1555.8 How Can Alkynes Be Reduced to Alkenes and Alkanes? 157Summary of Key Questions 158Quick Quiz 159Key Reactions 160Problems 161Looking Ahead 165Group Learning Activities 166CHEMICAL CONNECTIONS5A Catalytic Cracking and the Importance of Alkenes 13306 Chirality: The Handedness of Molecules 1676.1 What Are Stereoisomers? 1686.2 What Are Enantiomers? 1696.3 How Do We Designate the Configuration of a Stereocenter? 1736.4 What Is the 2n Rule? 1766.5 How Do We Describe the Chirality of Cyclic Molecules with Two Stereocenters? 1806.6 How Do We Describe the Chirality of Molecules with Three or More Stereocenters? 1826.7 What Are the Properties of Stereoisomers? 1836.8 How Is Chirality Detected in the Laboratory? 1846.9 What Is the Significance of Chirality in the Biological World? 1856.10 How Can Enantiomers Be Resolved? 186Summary of Key Questions 189Quick Quiz 190Problems 191Chemical Transformations 195Looking Ahead 196Group Learning Activities 196Putting It Together 196CHEMICAL CONNECTIONS6A Chiral Drugs 18707 Haloalkanes 2007.1 How Are Haloalkanes Named? 2017.2 What Are the Characteristic Reactions of Haloalkanes? 2037.3 What Are the Products of Nucleophilic Aliphatic Substitution Reactions? 2067.4 What Are the SN2 and SN1 Mechanisms for Nucleophilic Substitution? 2087.5 What Determines Whether SN1 or SN2 Predominates? 2117.6 How Can SN1 and SN2 Be Predicted Based on Experimental Conditions? 2177.7 What Are the Products of b-Elimination? 2197.8 What Are the E1 and E2 Mechanisms for b-Elimination? 2227.9 When Do Nucleophilic Substitution and b-Elimination Compete? 225Summary of Key Questions 229Quick Quiz 230Key Reactions 231Problems 231Chemical Transformations 236Looking Ahead 237Group Learning Activities 238CHEMICAL CONNECTIONS7A The Environmental Impact of Chlorofluorocarbons 2047B The Effect of Chlorofluorocarbon Legislation on Asthma Sufferers 22808 Alcohols, Ethers, and Thiols 2398.1 What Are Alcohols? 2408.2 What Are the Characteristic Reactions of Alcohols? 2468.3 What Are Ethers? 2608.4 What Are Epoxides? 2648.5 What Are Thiols? 2688.6 What Are the Characteristic Reactions of Thiols? 271Summary of Key Questions 272Quick Quiz 274Key Reactions 274Problems 275Chemical Transformations 279Looking Ahead 280Group Learning Activities 281CHEMICAL CONNECTIONS8A Nitroglycerin: An Explosive and a Drug 2438B Blood Alcohol Screening 2608C Ethylene Oxide: A Chemical Sterilant 26809 Benzene and Its Derivatives 2829.1 What Is the Structure of Benzene? 2839.2 What Is Aromaticity? 2869.3 How Are Benzene Compounds Named, and What Are Their Physical Properties? 2899.4 What Is the Benzylic Position, and How Does It Contribute to Benzene Reactivity? 2929.5 What Is Electrophilic Aromatic Substitution? 2959.6 What Is the Mechanism of Electrophilic Aromatic Substitution? 2969.7 How Do Existing Substituents on Benzene Affect Electrophilic Aromatic Substitution? 3059.8 What Are Phenols? 314Summary of Key Questions 321Quick Quiz 322Key Reactions 322Problems 324Chemical Transformations 329Looking Ahead 330Group Learning Activities 330CHEMICAL CONNECTIONS9A Carcinogenic Polynuclear Aromatics and Cancer 2939B Capsaicin, for Those Who Like It Hot 31810 Amines 33110.1 What Are Amines? 33310.2 How Are Amines Named? 33410.3 What Are the Characteristic Physical Properties of Amines? 33710.4 What Are the Acid?Base Properties of Amines? 34010.5 What Are the Reactions of Amines with Acids? 34410.6 How Are Arylamines Synthesized? 34610.7 How Do Amines Act as Nucleophiles? 347Summary of Key Questions 349Quick Quiz 350Key Reactions 350Problems 351Chemical Transformations 356Looking Ahead 357Group Learning Activities 357Putting It Together 357CHEMICAL CONNECTIONS10A Morphine as a Clue in the Design and Discovery of Drugs 33210B The Poison Dart Frogs of South America: Lethal Amines 33811 Spectroscopy 36111.1 What Is Electromagnetic Radiation? 36211.2 What Is Molecular Spectroscopy? 36411.3 What Is Infrared Spectroscopy? 36411.4 How Do We Interpret Infrared Spectra? 36711.5 What Is Nuclear Magnetic Resonance? 37811.6 What Is Shielding? 38011.7 What Is an NMR Spectrum? 38011.8 How Many Resonance Signals Will a Compound Yield in Its NMR Spectrum? 38211.9 What Is Signal Integration? 38511.10 What Is Chemical Shift? 38611.11 What Is Signal Splitting? 38811.12 What Is 13C-NMR Spectroscopy, and How Does It Differ from 1H-NMR Spectroscopy? 39111.13 How Do We Solve an NMR Problem? 394Summary of Key Questions 398Quick Quiz 400Problems 401Looking Ahead 414Group Learning Activities 415CHEMICAL CONNECTIONS11A Infrared Spectroscopy: A Window on Brain Activity 36811B Magnetic Resonance Imaging 39112 Aldehydes and Ketones 41612.1 What Are Aldehydes and Ketones? 41712.2 How Are Aldehydes and Ketones Named? 41712.3 What Are the Physical Properties of Aldehydes and Ketones? 42112.4 What Is the Most Common Reaction Theme of Aldehydes and Ketones? 42212.5 What Are Grignard Reagents, and How Do They React with Aldehydes and Ketones? 42312.6 What Are Hemiacetals and Acetals? 42712.7 How Do Aldehydes and Ketones React with Ammonia and Amines? 43412.8 What Is Keto?Enol Tautomerism? 43712.9 How Are Aldehydes and Ketones Oxidized? 44112.10 How Are Aldehydes and Ketones Reduced? 443Summary of Key Questions 445Quick Quiz 447Key Reactions 447Problems 448Chemical Transformations 454Spectroscopy 455Looking Ahead 456Group Learning Activities 456CHEMICAL CONNECTIONS12A A Green Synthesis of Adipic Acid 44213 Carboxylic Acids 45713.1 What Are Carboxylic Acids? 45813.2 How Are Carboxylic Acids Named? 45813.3 What Are the Physical Properties of Carboxylic Acids? 46113.4 What Are the Acid?Base Properties of Carboxylic Acids? 46213.5 How Are Carboxyl Groups Reduced? 46613.6 What Is Fischer Esterification? 47013.7 What Are Acid Chlorides? 47313.8 What Is Decarboxylation? 475Summary of Key Questions 479Quick Quiz 480Key Reactions 480Problems 481Chemical Transformations 486Looking Ahead 487Group Learning Activities 487CHEMICAL CONNECTIONS13A From Willow Bark to Aspirin and Beyond 46613B Esters as Flavoring Agents 47213C Ketone Bodies and Diabetes 47614 Functional Derivatives of Carboxylic Acids 48814.1 What Are Some Derivatives of Carboxylic Acids, and How Are They Named? 48914.2 What Are the Characteristic Reactions of Carboxylic Acid Derivatives? 49514.3 What Is Hydrolysis? 49614.4 How Do Carboxylic Acid Derivatives React with Alcohols? 50114.5 How Do Carboxylic Acid Derivatives React with Ammonia and Amines? 50314.6 How Can Functional Derivatives of Carboxylic Acids Be Interconverted? 50514.7 How Do Esters React with Grignard Reagents? 50714.8 How Are Derivatives of Carboxylic Acids Reduced? 509Summary of Key Questions 513Quick Quiz 514Key Reactions 515Problems 516Chemical Transformations 522Looking Ahead 523Group Learning Activities 523Putting It Together 523CHEMICAL CONNECTIONS14A Ultraviolet Sunscreens and Sunblocks 49014B From Moldy Clover to a Blood Thinner 49114C The Penicillins and Cephalosporins: b-Lactam Antibiotics 49214D The Pyrethrins: Natural Insecticides of Plant Origin 50314E Systematic Acquired Resistance in Plants 50615 Enolate Anions 52615.1 What Are Enolate Anions, and How Are They Formed? 52715.2 What Is the Aldol Reaction? 53015.3 What Are the Claisen and Dieckmann Condensations? 53715.4 How Are Aldol Reactions and Claisen Condensations Involved in Biological Processes? 54515.5 What Is the Michael Reaction? 547Summary of Key Questions 554Quick Quiz 554Key Reactions 555Problems 556Chemical Transformations 561Looking Ahead 562Group Learning Activities 563CHEMICAL CONNECTIONS15A Drugs That Lower Plasma Levels of Cholesterol 54615B Antitumor Compounds: The Michael Reaction in Nature 55316 Organic Polymer Chemistry 56416.1 What Is the Architecture of Polymers? 56516.2 How Do We Name and Show the Structure of a Polymer? 56516.3 What Is Polymer Morphology? Crystalline versus Amorphous Materials 56716.4 What Is Step-Growth Polymerization? 56816.5 What Are Chain-Growth Polymers? 57316.6 What Plastics Are Currently Recycled in Large Quantities? 579Summary of Key Questions 580Quick Quiz 581Key Reactions 582Problems 582Looking Ahead 584Group Learning Activities 585CHEMICAL CONNECTIONS16A Stitches That Dissolve 57316B Paper or Plastic? 57517 Carbohydrates 58617.1 What Are Carbohydrates? 58617.2 What Are Monosaccharides? 58717.3 What Are the Cyclic Structures of Monosaccharides? 59117.4 What Are the Characteristic Reactions of Monosaccharides? 59617.5 What Are Disaccharides and Oligosaccharides? 60117.6 What Are Polysaccharides? 604Summary of Key Questions 606Quick Quiz 608Key Reactions 608Problems 609Looking Ahead 614Group Learning Activities 614Putting It Together 615CHEMICAL CONNECTIONS17A Relative Sweetness of Carbohydrate and Artificial Sweeteners 60217B A, B, AB, and O Blood-Group Substances 60318 Amino Acids and Proteins 61918.1 What Are the Many Functions of Proteins? 62018.2 What Are Amino Acids? 62018.3 What Are the Acid?Base Properties of Amino Acids? 62318.4 What Are Polypeptides and Proteins? 63018.5 What Is the Primary Structure of a Polypeptide or Protein? 63118.6 What Are the Three-Dimensional Shapes of Polypeptides and Proteins? 635Summary of Key Questions 642Quick Quiz 643Key Reactions 644Problems 645Looking Ahead 648Group Learning Activities 648CHEMICAL CONNECTIONS18A Spider Silk: A Chemical and Engineering Wonder of Nature 64019 Lipids 64919.1 What Are Triglycerides? 65019.2 What Are Soaps and Detergents? 65319.3 What Are Phospholipids? 65519.4 What Are Steroids? 65719.5 What Are Prostaglandins? 66219.6 What Are Fat-Soluble Vitamins? 665Summary of Key Questions 668Quick Quiz 669Problems 669Looking Ahead 672Group Learning Activities 673CHEMICAL CONNECTIONS19A Snake Venom Phospholipases 65719B Nonsteroidal Estrogen Antagonists 66120 Nucleic Acids (Online Chapter) 67420.1 What Are Nucleosides and Nucleotides? 67520.2 What Is the Structure of DNA? 67820.3 What Are Ribonucleic Acids (RNA)? 68520.4 What Is the Genetic Code? 68720.5 How Is DNA Sequenced? 689Summary of Key Questions 694Quick Quiz 696Problems 696Group Learning Activities 699CHEMICAL CONNECTIONS20A The Search for Antiviral Drugs 67720B DNA Fingerprinting 69421 The Organic Chemistry of Metabolism (Online Chapter) 70021.1 What Are the Key Participants in Glycolysis, the b-Oxidation of Fatty Acids, and the Citric Acid Cycle? 70121.2 What Is Glycolysis? 70621.3 What Are the Ten Reactions of Glycolysis? 70721.4 What Are the Fates of Pyruvate? 71121.5 What Are the Reactions of the b-Oxidation of Fatty Acids? 71321.6 What Are the Reactions of the Citric Acid Cycle? 717Summary of Key Questions 720Quick Quiz 721Key Reactions 722Problems 722Group Learning Activities 724Appendix 1 Acid Ionization Constants for the Major Classes of Organic Acids A.1Appendix 2 Characteristic 1H-NMR Chemical Shifts A.2Appendix 3 Characteristic 13C-NMR Chemical Shifts A.3Appendix 4 Characteristic Infrared Absorption Frequencies A.4Glossary G.1Answers Section Ans.1Index I.1
