Organic Chemistry

Paperback

Smith, Janice Gorzynski 저자(글)

McGraw-Hill · 2004년 12월 31일

책 소개

작가정보

저자(글) Smith, Janice Gorzynski

출간작으로 『유기화학』 등이 있다.

목차

• 
  List of How To's xvii
  List of Mechanisms xviii
  List of Selected Applications xxi
  Preface xxiii
  Acknowledgments xxv
  Guided Tour xxx
  Prologue 1
  What Is Organic Chemistry? 2(1)
  Some Representative Organic Molecules 2(2)
  Palytoxin---An Example of a Very Complex Organic Compound 4(2)
  Structure and Bonding 6(48)
  The Periodic Table 7(3)
  Bonding 10(2)
  Lewis Structures 12(5)
  Lewis Structures Continued 17(2)
  Resonance 19(4)
  Determining Molecular Shape 23(5)
  Drawing Organic Structures 28(4)
  Hybridization 32(5)
  Ethane, Ethylene, and Acetylene 37(5)
  Bond Length and Bond Strength 42(1)
  Electronegativity and Bond Polarity 43(2)
  Polarity of Molecules 45(2)
  Capsaicin---A Representative Organic Molecule 47(1)
  Key Concepts---Structure and Bonding 47(7)
  Problems 49(5)
  Acids and Bases 54(26)
  Bronsted---Lowry Acids and Bases 55(1)
  Reactions of Bronsted--Lowry Acids and Bases 56(2)
  Acid Strength and pKa 58(3)
  Predicting the Outcome of Acid--Base Reactions 61(1)
  Factors that Determine Acid Strength 62(8)
  Common Acids and Bases 70(1)
  Aspirin 71(1)
  Lewis Acids and Bases 72(3)
  Key Concepts---Acids and Bases 75(5)
  Problems 76(4)
  Introduction to Organic Molecules and Functional Groups 80(32)
  Functional Groups 81(1)
  An Overview of Functional Groups 82(4)
  Biomolecules 86(1)
  Intermolecular Forces 86(4)
  Physical Properties 90(7)
  Application: Vitamins 97(1)
  Application of Solubility: Soap 98(2)
  Application: The Cell Membrane 100(2)
  Functional Groups and Reactivity 102(2)
  Key Concepts---Introduction to Organic Molecules and Functional Groups 104(8)
  Problems 106(6)
  Alkanes 112(44)
  Alkanes---An Introduction 113(4)
  Cycloalkanes 117(1)
  An Introduction to Nomenclature 117(1)
  Naming Alkanes 118(6)
  Naming Cycloalkanes 124(2)
  Common Names 126(1)
  Fossil Fuels 127(1)
  Physical Properties of Alkanes 128(1)
  Conformations of Acyclic Alkanes---Ethane 129(4)
  Conformations of Butane 133(3)
  An Introduction to Cycloalkanes 136(1)
  Cyclohexane 137(3)
  Substituted Cycloalkanes 140(5)
  Oxidation of Alkanes 145(3)
  Lipids---Part I 148(1)
  Key Concepts---Alkanes 149(7)
  Problems 151(5)
  Stereochemistry 156(34)
  Starch and Cellulose 157(2)
  The Two Major Classes of Isomers 159(1)
  Looking Glass Chemistry---Chiral and Achiral Molecules 160(3)
  Stereogenic Centers 163(2)
  Stereogenic Centers in Cyclic Compounds 165(2)
  Labeling Stereogenic Centers with R or S 167(4)
  Diastereomers 171(2)
  Meso Compounds 173(2)
  R and S Assignments in Compounds with Two or More Stereogenic Centers 175(1)
  Disubstituted Cycloalkanes 176(1)
  Isomers---A Summary 177(1)
  Physical Properties of Stereoisomers 178(4)
  Chemical Properties of Enantiomers 182(2)
  Key Concepts---Stereochemistry 184(6)
  Problems 185(5)
  Understanding Organic Reactions 190(30)
  Writing Equations for Organic Reactions 191(1)
  Kinds of Organic Reactions 192(2)
  Bond Breaking and Bond Making 194(4)
  Bond Dissociation Energy 198(3)
  Thermodynamics 201(2)
  Enthalpy and Entropy 203(2)
  Energy Diagrams 205(2)
  Energy Diagram for a Two-Step Reaction Mechanism 207(3)
  Kinetics 210(2)
  Catalysts 212(1)
  Enzymes 213(1)
  Key Concepts---Understanding Organic Reactions 214(6)
  Problems 216(4)
  Alkyl Halides and Nucleophilic Substitution 220(50)
  Introduction to Alkyl Halides 221(1)
  Nomenclature 222(1)
  Physical Properties 223(1)
  Interesting Alkyl Halides 224(2)
  The Polar Carbon--Halogen Bond 226(1)
  General Features of Nucleophilic Substitution 226(2)
  The Leaving Group 228(2)
  The Nucleophile 230(4)
  Possible Mechanisms for Nucleophilic Substitution 234(1)
  Two Mechanisms for Nucleophilic Substitution 235(1)
  The SN2 Mechanism 236(5)
  Application: Useful SN2 Reactions 241(3)
  The SN1 Mechanism 244(4)
  Carbocation Stability 248(2)
  The Hammond Postulate 250(3)
  Application: SN1 Reactions, Nitrosamines, and Cancer 253(1)
  When Is the Mechanism SN1 or SN2? 254(5)
  Vinyl Halides and Aryl Halides 259(1)
  Organic Synthesis 260(2)
  Key Concepts---Alkyl Halides and Nucleophilic Substitution 262(8)
  Problems 263(7)
  Alkyl Halides and Elimination Reactions 270(32)
  General Features of Elimination 271(2)
  Alkenes---The Products of Elimination Reactions 273(4)
  The Mechanisms of Elimination 277(1)
  The E2 Mechanism 277(4)
  The Zaitsev Rule 281(2)
  The El Mechanism 283(2)
  SN1 and E1 Reactions 285(2)
  Stereochemistry of the E2 Reaction 287(2)
  When Is the Mechanism E1 or E2? 289(1)
  E2 Reactions and Alkyne Synthesis 290(2)
  When Is the Reaction SN1, SN2, E1, or E2? 292(4)
  Key Concepts---Alkyl Halides and Elimination Reactions 296(6)
  Problems 297(5)
  Alcohols, Ethers, and Epoxides 302(44)
  Introduction 303(1)
  Structure and Bonding 304(1)
  Nomenclature 304(3)
  Physical Properties 307(1)
  Interesting Alcohols, Ethers, and Epoxides 308(3)
  Preparation of Alcohols, Ethers, and Epoxides 311(2)
  General Features---Reactions of Alcohols, Ethers, and Epoxides 313(1)
  Dehydration of Alcohols to Alkenes 314(4)
  Carbocation Rearrangements 318(2)
  Dehydration Using POCI3 and Pyridine 320(2)
  Conversion of Alcohols to Alkyl Halides with HX 322(3)
  Conversion of Alcohols to Alkyl Halides with SOCI2 and PBr3 325(2)
  Tosylate---Another Good Leaving Group 327(3)
  Reaction of Ethers with Strong Acid 330(2)
  Reaction of Epoxides 332(4)
  Application: Epoxides, Leukotrienes, and Asthma 336(1)
  Application: Benzo[a]pyrene, Epoxides, and Cancer 337(1)
  Key Concepts---Alcohols, Ethers, and Epoxides 338(8)
  Problems 340(6)
  Alkenes 346(40)
  Introduction 347(1)
  Calculating Degrees of Unsaturation 348(1)
  Nomenclature 349(4)
  Physical Properties 353(1)
  Interesting Alkenes 353(1)
  Lipids---Part 2 354(2)
  Preparation of Alkenes 356(1)
  Introduction to Addition Reactions 357(1)
  Hydrohalogenation---Electrophilic Addition of HX 358(3)
  Markovnikov's Rule 361(2)
  Stereochemistry of Electrophilic Addition of HX 363(2)
  Hydration---Electrophilic Addition of Water 365(1)
  Halogenation---Addition of Halogen 366(2)
  Stereochemistry of Halogenation 368(2)
  Halohydrin Formation 370(3)
  Hydroboration--Oxidation 373(4)
  Keeping Track of Reactions 377(1)
  Alkenes in Organic Synthesis 378(2)
  Key Concepts---Alkenes 380(6)
  Problems 381(5)
  Alkynes 386(26)
  Introduction 387(1)
  Nomenclature 388(1)
  Physical Properties 389(1)
  Interesting Alkynes 389(2)
  Preparation of Alkynes 391(1)
  Introduction to Alkyne Reactions 392(1)
  Addition of Hydrogen Halides 393(2)
  Addition of Halogen 395(1)
  Addition of Water 396(3)
  Hydroboration--Oxidation 399(2)
  Reaction of Acetylide Anions 401(3)
  Synthesis 404(3)
  Key Concepts---Alkynes 407(5)
  Problems 408(4)
  Oxidation and Reduction 412(34)
  Introduction 413(1)
  Reducing Agents 414(1)
  Reduction of Alkenes 415(3)
  Application: Hydrogenation of Oils 418(1)
  Reduction of Alkynes 419(3)
  The Reduction of Polar C--X σ Bonds 422(1)
  Oxidizing Agents 423(2)
  Epoxidation 425(3)
  Dihydroxylation 428(2)
  Oxidative Cleavage of Alkenes 430(2)
  Oxidative Cleavage of Alkynes 432(1)
  Oxidation of Alcohols 433(3)
  Application: The Oxidation of Ethanol 436(1)
  Sharpless Epoxidation 436(3)
  Key Concepts---Oxidation and Reduction 439(7)
  Problems 441(5)
  Radical Reactions 446(32)
  Introduction 447(1)
  General Features of Radical Reactions 448(2)
  Halogenation of Alkanes 450(1)
  The Mechanism of Halogenation 451(2)
  Chlorination of Other Alkanes 453(1)
  Chlorination versus Bromination 454(3)
  Halogenation as a Tool in Organic Synthesis 457(1)
  The Stereochemistry of Halogenation Reactions 457(2)
  Application: The Ozone Layer and CFCs 459(2)
  Redical Halogenation at an Allylic Carbon 461(4)
  Application: Oxidation of Unsaturated Lipids 465(1)
  Application: Antioxidants 466(1)
  Radical Addition Reactions to Double Bonds 467(3)
  Polymers and Polymerization 470(2)
  Key Concepts---Radical Reactions 472(6)
  Problems 473(5)
  Mass Spectrometry and Infrared Spectroscopy 478(26)
  Mass Spectrometry 479(4)
  Alkyl Halides and the M + 2 Peak 483(1)
  Other Types of Mass Spectrometry 484(3)
  Electromagnetic Radiation 487(1)
  Infrared Spectroscopy 488(2)
  IR Absorptions 490(7)
  IR and Structure Determination 497(2)
  Key Concepts---Mass Spectrometry and Infrared Spectroscopy 499(5)
  Problems 500(4)
  Nuclear Magnetic Resonance Spectroscopy 504(40)
  An Introduction to NMR Spectroscopy 505(3)
  1H NMR: Number of Signals 508(3)
  1H NMR: Position of Signals 511(3)
  The Chemical Shift of Protons on sp2 and sp Hybridized Carbons 514(2)
  1H NMR: Intensity of Signals 516(2)
  1H NMR: Spin--Spin Splitting 518(4)
  More Complex Examples of Splitting 522(3)
  Spin--Spin Splitting in Alkenes 525(2)
  Other Facts About 1H NMR Spectroscopy 527(2)
  Using 1H NMR to Identify an Unknown 529(2)
  13C NMR Spectroscopy 531(4)
  Magnetic Resonance Imaging (MRI) 535(1)
  Key Concepts---Nuclear Magnetic Resonance Spectroscopy 536(8)
  Problems 537(7)
  Conjugation, Resonance, and Dienes 544(34)
  Conjugation 545(2)
  Resonance and Allylic Carbocations 547(1)
  Common Examples of Resonance 548(2)
  The Resonance Hybrid 550(1)
  Electron Delocalization, Hybridization, and Geometry 551(1)
  Conjugated Dienes 552(1)
  Interesting Dienes and Polyenes 553(1)
  The Carbon--Carbon σ Bond Length in 1,3-Butadiene 553(2)
  Stability of Conjugated Dienes 555(1)
  Electrophilic Addition: 1,2-Versus, 1,4-Addition 556(2)
  Kinetic Versus Thermodynamic Products 558(3)
  The Diels--Alder Reaction 561(2)
  Specific Rules Governing the Diels--Alder Reaction 563(4)
  Other Facts About the Diels--Alder Reaction 567(2)
  Conjugated Dienes and Ultraviolet Light 569(2)
  Key Concepts---Conjugation, Resonance, and Dienes 571(7)
  Problems 571(7)
  Benzene and Aromatic Compounds 578(30)
  Background 579(1)
  The Structure of Benzene 580(1)
  Nomenclature of Benzene Derivatives 581(2)
  Spectroscopic Properties 583(1)
  Interesting Aromatic Compounds 584(1)
  Benzene's Unusual Stability 585(2)
  The Criteria for Aromaticity---Huckel's Rule 587(3)
  Examples of Aromatic Compounds 590(6)
  What Is the Basis of Huckel's Rule? 596(2)
  The Inscribed Polygon Method for Predicting Aromaticity 598(3)
  Buckminsterfullerene---Is It Aromatic? 601(1)
  Key Concepts---Benzene and Aromatic Compounds 602(6)
  Problems 602(6)
  Electrophilic Aromatic Substitution 608(44)
  Electrophilic Aromatic Substitution 609(1)
  The General Mechanism 609(3)
  Halogenation 612(1)
  Nitration and Sulfonation 613(1)
  Friedel--Crafts Alkylation and Friedel--Crafts Acylation 614(6)
  Substituted Benzenes 620(4)
  Electrophilic Aromatic Substitution of Substituted Benzenes 624(2)
  Why Substituents Activate or Deactivate a Benzene Ring 626(2)
  Orientation Effects in Substituted Benzenes 628(3)
  Limitations on Electrophilic Substitution Reactions with Substituted Benzenes 631(2)
  Disubstituted Benzenes 633(2)
  Synthesis of Benzene Derivatives 635(1)
  Halogenation of Alkyl Benzenes 636(2)
  Oxidation and Reduction of Substituted Benzenes 638(3)
  Multistep Synthesis 641(3)
  Key Concepts---Electrophilic Aromatic Substitution 644(8)
  Problems 646(6)
  Carboxylic Acids and the Acidity of the O--H Bond 652(32)
  Structure and Bonding 653(1)
  Nomenclature 654(3)
  Physical Properties 657(1)
  Spectroscopic Properties 658(1)
  Interesting Carboxylic Acids 659(1)
  Aspirin, Arachidonic Acid, and Prostaglandins 660(1)
  Preparation of Carboxylic Acids 661(2)
  Reactions of Carboxylic Acids---General Features 663(1)
  Carboxylic Acids---Strong Organic Bronsted--Lowry Acids 664(3)
  Inductive Effects in Aliphatic Carboxylic Acids 667(1)
  Substituted Benzoic Acids 668(2)
  Extraction 670(3)
  Sulfonic Acids 673(1)
  Amino Acids 673(3)
  Key Concepts---Carboxylic Acids and the Acidity of the O--H Bond 676(8)
  Problems 678(6)
  Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction 684(48)
  Introduction 685(1)
  General Reactions of Carbonyl Compounds 686(3)
  A Preview of Oxidation and Reduction 689(1)
  Reduction of Aldehydes and Ketones 690(3)
  The Stereochemistry of Carbonyl Reduction 693(1)
  Enantioselective Carbonyl Reductions 693(3)
  Reduction of Carboxylic Acids and Their Derivatives 696(4)
  Oxidation of Aldehydes 700(1)
  Organometallic Reagents 701(3)
  Reaction of Organometallic Reagents with Aldehydes and Ketones 704(3)
  Retrosynthetic Analysis of Grignard Products 707(2)
  Protecting Groups 709(2)
  Reaction of Organometallic Reagents with Carboxylic Acid Derivatives 711(3)
  Reaction of Organometallic Reagents with Other Compounds 714(2)
  α,β-Unsaturated Carbonyl Compounds 716(3)
  Summary---The Reactions of Organometallic Reagents 719(1)
  Synthesis 719(3)
  Key Concepts---Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction 722(10)
  Problems 725(7)
  Aldehydes and Ketones---Nucleophilic Addition 732(48)
  Introduction 733(1)
  Nomenclature 734(3)
  Physical Properties 737(1)
  Spectroscopic Properties 738(2)
  Interesting Aldehydes and Ketones 740(1)
  Preparation of Aldehydes and Ketones 741(2)
  Reactions of Aldehydes and Ketones---General Considerations 743(2)
  Nucleophilic Addition of H- and R- ---A Review 745(3)
  Nucleophilic Addition of -CN 748(1)
  The Wittig Reaction 749(5)
  Addition of 1 Amines 754(2)
  Addition of 2 Amines 756(3)
  Addition of H2O---Hydration 759(3)
  Addition of Alcohols---Acetal Formation 762(3)
  Acetals as Protecting Groups 765(1)
  Cyclic Hemiacetals 766(3)
  An Introduction to Carbohydrates 769(2)
  Key Concepts---Aldehydes and Ketones---Nucleophilic Addition 771(9)
  Problems 773(7)
  Carboxylic Acids and Their Derivatives---Nucleophilic Acyl Substitution 780(52)
  Introduction 781(2)
  Structure and Bonding 783(2)
  Nomenclature 785(3)
  Physical Properties 788(1)
  Spectroscopic Properties 789(1)
  Interesting Esters and Amides 790(2)
  Introduction to Nucleophilic Acyl Substitution 792(4)
  Reactions of Acid Chlorides 796(1)
  Reactions of Anhydrides 797(2)
  Reactions of Carboxylic Acids 799(5)
  Reactions of Esters 804(2)
  Application: Lipid Hydrolysis 806(2)
  Reactions of Amides 808(1)
  Application: The Mechanism of Action of β-Lactam Antibiotics 809(1)
  Summary of Nucleophilic Acyl Substitution Reactions 810(1)
  Natural and Synthetic Fibers 811(2)
  Biological Acylation Reactions 813(2)
  Nitriles 815(5)
  Key Concepts---Carboxylic Acids and Their Derivatives---Nucleophilic Acyl Substitution 820(12)
  Problems 823(9)
  Substitution Reactions of Carbonyl Compounds at the α Carbon 832(32)
  Introduction 833(1)
  Enols 834(2)
  Enolates 836(5)
  Enolates of Unsymmetrical Carbonyl Compounds 841(2)
  Racemization at the α Carbon 843(1)
  A Preview of Reactions at the α Carbon 844(1)
  Halogenation at the α Carbon 844(4)
  Direct Enolate Alkylation 848(3)
  Malonic Ester Synthesis 851(4)
  Acetoacetic Ester Synthesis 855(3)
  Key Concepts---Substitution Reactions of Carbonyl Compounds at the α Carbon 858(6)
  Problems 859(5)
  Carbonyl Condensation Reactions 864(28)
  The Aldol Reaction 865(4)
  Crossed Aldol Reactions 869(3)
  Directed Aldol Reactions 872(1)
  Intramolecular Aldol Reactions 873(2)
  The Claisen Reaction 875(2)
  The Crossed Claisen and Related Reactions 877(2)
  The Dieckmann Reaction 879(1)
  The Michael Reaction 880(2)
  The Robinson Annualation 882(3)
  Key Concepts---Carbonyl Condensation Reactions 885(7)
  Problems 887(5)
  Amines 892(50)
  Introduction 893(1)
  Structure and Bonding 894(1)
  Nomenclature 895(2)
  Physical Properties 897(1)
  Spectroscopic Properties 898(1)
  Interesting and Useful Amines 899(4)
  Preparation of Amines 903(6)
  Reactions of Amines---General Features 909(1)
  Amines as Bases 909(2)
  Relative Basicity of Amines and Other Compounds 911(6)
  Amines as Nucleophiles 917(2)
  Hofmann Elimination 919(3)
  Reaction of Amines with Nitrous Acid 922(2)
  Substitution Reactions of Aryl Diazonium Salts 924(4)
  Coupling Reactions of Aryl Diazonium Salts 928(2)
  Application: Perkin's Mauveine and Synthetic Dyes 930(2)
  Application: Sulfa Drugs 932(1)
  Key Concepts---Amines 933(9)
  Problems 935(7)
  Lipids 942(28)
  Introduction 943(1)
  Waxes 944(1)
  Triacylglycerols 944(4)
  Phospholipids 948(2)
  Fat-soluble Vitamins 950(2)
  Eicosanoids 952(3)
  Terpenes 955(5)
  Steroids 960(4)
  Key Concepts---Lipids 964(6)
  Problems 965(5)
  Carbohydrates 970(42)
  Introduction 971(1)
  Monosaccharides 972(4)
  The Family of D-Aldoses 976(2)
  The Family of D-Ketoses 978(1)
  Physical Properties of Monosaccharides 978(1)
  The Cyclic Forms of Monosaccharides 979(5)
  Glycosides 984(3)
  Reactions of Monosaccharides at the OH Groups 987(1)
  Reactions at the Carbonyl Group---Oxidation and Reduction 988(3)
  Reactions at the Carbonyl Group---Adding or Removing One Carbon Atom 991(3)
  The Fischer Proof of the Structure of Glucose 994(3)
  Disaccharides 997(2)
  Polysaccharides 999(2)
  Other Important Sugars and Their Derivatives 1001(4)
  Key Concepts---Carbohydrates 1005(7)
  Problems 1007(5)
  Amino Acids and Proteins 1012
  Amino Acids 1013(3)
  Synthesis of Amino Acids 1016(3)
  Separation of Amino Acids 1019(4)
  Enantioselective Synthesis of Amino Acids 1023(1)
  Peptides 1024(4)
  Peptide Synthesis 1028(4)
  Automated Peptide Synthesis 1032(3)
  Protein Structure 1035(5)
  Important Proteins 1040(3)
  Key Concepts---Amino Acids and Proteins 1043
  Problems 1044
  Appendix A Common Abbreviations, Arrows, and Symbols 1(2)
  Appendix B pKa, Values for Selected Compounds 3(2)
  Appendix C Bond Dissociation Energies for Some Common Bonds 5(2)
  Appendix D Characteristic IR Absorption Frequencies 7(2)
  Appendix E Characteristic 1H NMR Absorptions 9(2)
  Appendix F General Types of Organic Reactions 11(2)
  Appendix G How to Synthesize Particular Functional Groups 13(4)
  Appendix H Reactions that Form Carbon--Carbon Bonds 17
  Glossary 1(1)
  Credits 1(1)
  Index 1

기본정보

ISBN	9780073101705 ( 0073101702 )
발행(출시)일자	2004년 12월 31일
쪽수	준비중