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Organic Chemistry, International Adaptation, 4th Edition

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ÁöÀºÀÌ :  David R. Klein
¹ßÇàÀÏ :  2022
ISBN :  9781119820833
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ÃâÆÇ»ç :  Wiley

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Organic Chemistry
High-Resolution NMR Techniques in Organic Chemistry 2/e

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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

World Links Biomimicry and Gecko Feet 37

BioLinks Drug- Receptor Interactions 38

1.14 Solubility 39

BioLinks Propofol: The Importance of Drug Solubility 40

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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

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3 Acids and Bases 91

3.1 Introduction to Br©ªnsted- Lowry Acids and Bases 92

3.2 Flow of Electron Density: Curved- Arrow Notation 92

BioLinks Antacids and Heartburn 94

3.3 Br©ªnsted- Lowry Acidity: Quantitative Perspective 95

BioLinks Drug Distribution and pK a 101

3.4 Br©ªnsted- Lowry Acidity: Qualitative Perspective 102

3.5 Br©ªnsted- 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

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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

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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

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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

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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 SystemsMethylation 293

7.6 The S N 1 Mechanism 295

7.7 Solvent Effects in Substitution Reactions 301

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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

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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

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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

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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

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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

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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

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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

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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 ChromatographyMass Spectrometry 682

15.15 Liquid ChromatographyMass 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 DielsAlder 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

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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

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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 FriedelCrafts Alkylation 852

19.6 FriedelCrafts 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

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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 BaeyerVilliger Oxidation of Aldehydes and Ketones 933

20.12 Synthesis Strategies 935

20.13 Spectroscopic Analysis of Aldehydes and Ketones 938

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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

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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

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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

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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 SimmonsSmith 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

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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

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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

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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

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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

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Appendix A: Nomenclature of Polyfunctional Compounds A1

Appendix B: Multiple Choice Questions A5

Glossary G1

Index I1

Selected Answers*