Organic Chemistry 1st Edition Klein Test Bank

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

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2 Molecular Representations 50

2.1 Molecular Representations 51

2.2 Drawing Bond-Line Structures 53

2.3 Identifying Functional Groups 55

BioLinks Marine Natural Products 56

2.4 Carbon Atoms with Formal Charges 58

2.5 Identifying Lone Pairs 58

2.6 Three-Dimensional Bond-Line Structures 61

BioLinks The Opioids 62

2.7 Introduction to Resonance 63

2.8 Curved Arrows 65

2.9 Formal Charges in Resonance Structures 68

2.10 Drawing Resonance Structures via Pattern Recognition 70

2.11 Assessing the Relative Importance of Resonance Structures 75

2.12 The Resonance Hybrid 79

2.13 Delocalized and Localized Lone Pairs 81

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3 Acids and Bases 93

3.1 Introduction to Brønsted-Lowry Acids and Bases 94

3.2 Flow of Electron Density: Curved-Arrow Notation 94

BioLinks Antacids and Heartburn 96

3.3 Brønsted-Lowry Acidity: Comparing pK_a values 97

BioLinks Drug Distribution and pK_a 103

3.4 Brønsted-Lowry Acidity: Factors Affecting the Stability of Anions 104

3.5 Brønsted-Lowry Acidity: Assessing the Relative Acidity of Cationic Acids 115

3.6 Position of Equilibrium and Choice of Reagents 120

3.7 Leveling Effect 123

3.8 Solvating Effects 124

3.9 Counterions 125

WorldLinks Baking Soda versus Baking Powder 125

3.10 Lewis Acids and Bases 126

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4 Alkanes and Cycloalkanes 138

4.1 Introduction to Alkanes 139

4.2 Nomenclature of Alkanes 139

WorldLinks Pheromones: Chemical Messengers 143

BioLinks Naming Drugs 151

4.3 Constitutional Isomers of Alkanes 152

4.4 Relative Stability of Isomeric Alkanes 153

4.5 Sources and Uses of Alkanes 154

WorldLinks An Introduction to Polymers 156

4.6 Drawing Newman Projections 156

4.7 Conformational Analysis of Ethane and Propane 158

4.8 Conformational Analysis of Butane 160

BioLinks Drugs and Their Conformations 164

4.9 Cycloalkanes 164

BioLinks Cyclopropane as an Inhalation Anesthetic 166

4.10 Conformations of Cyclohexane 167

4.11 Drawing Chair Conformations 168

4.12 Monosubstituted Cyclohexane 170

4.13 Disubstituted Cyclohexane 172

4.14 cis-trans Stereoisomerism 176

4.15 Polycyclic Systems 177

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5 Stereoisomerism 188

5.1 Overview of Isomerism 189

5.2 Introduction to Stereoisomerism 190

WorldLinks The Sense of Smell 195

5.3 Designating Configuration Using the Cahn-Ingold-Prelog System 195

BioLinks Chiral Drugs 200

5.4 Optical Activity 201

5.5 Stereoisomeric Relationships: Enantiomers and Diastereomers 207

5.6 Symmetry and Chirality 210

5.7 Fischer Projections 214

5.8 Conformationally Mobile Systems 216

5.9 Chiral Compounds that Lack a Chiral Center 217

5.10 Resolution of Enantiomers 218

5.11 E and Z Designations for Diastereomeric Alkenes 220

BioLinks Phototherapy Treatment for Neonatal Jaundice 222

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6 Chemical Reactivity and Mechanisms 233

6.1 Enthalpy 234

6.2 Entropy 237

6.3 Gibbs Free Energy 239

WorldLinks Explosives 240

WorldLinks Do Living Organisms Violate the Second Law of Thermodynamics? 242

6.4 Equilibria 242

6.5 Kinetics 244

BioLinks Nitroglycerin: An Explosive with Medicinal Properties 247

WorldLinks Beer Making 248

6.6 Reading Energy Diagrams 249

6.7 Nucleophiles and Electrophiles 252

6.8 Mechanisms and Arrow Pushing 256

6.9 Combining the Patterns of Arrow Pushing 261

6.10 Drawing Curved Arrows 263

6.11 Carbocation Rearrangements 266

6.12 Reversible and Irreversible Reaction Arrows 268

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7 Alkyl Halides: Nucleophilic Substitution and Elimination Reactions 280

7.1 Introduction to Substitution and Elimination Reactions 281

7.2 Nomenclature and Uses of Alkyl Halides 282

7.3 S_N2 Reactions 286

BioLinks Pharmacology and Drug Design 292

7.4 Nucleophilic Strength in S_N2 Reactions 294

BioLinks S_N2 Reactions in Biological Systems—Methylation 295

7.5 Introduction to E2 Reactions 296

7.6 Stability of Alkenes and Cycloalkenes 299

7.7 Regiochemical and Stereochemical Outcomes for E2 Reactions 301

7.8 Unimolecular Reactions (S_N1 and E1) 311

7.9 Predicting Products: Substitution vs. Elimination 320

7.10 Substitution and Elimination Reactions with Other Substrates 327

7.11 Synthesis Strategies 331

BioLinks Radiolabeled Compounds in Diagnostic Medicine 338

7.12 Solvent Effects in Substitution Reactions 339

SpecialTopic Kinetic Isotope Effects 343

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8 Addition Reactions of Alkenes 356

8.1 Introduction to Addition Reactions 357

8.2 Alkenes in Nature and in Industry 358

WorldLinks Pheromones to Control Insect Populations 358

8.3 Nomenclature of Alkenes 359

8.4 Addition vs. Elimination: A Thermodynamic Perspective 361

8.5 Hydrohalogenation 363

WorldLinks Cationic Polymerization and Polystyrene 370

8.6 Acid-Catalyzed Hydration 371

8.7 Oxymercuration-Demercuration 375

8.8 Hydroboration-Oxidation 376

8.9 Catalytic Hydrogenation 382

WorldLinks Partially Hydrogenated Fats and Oils 387

8.10 Halogenation and Halohydrin Formation 388

8.11 Anti Dihydroxylation 392

8.12 Syn Dihydroxylation 395

8.13 Oxidative Cleavage 396

8.14 Predicting the Products of an Addition Reaction 398

8.15 Synthesis Strategies 400

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9 Alkynes 417

9.1 Introduction to Alkynes 418

BioLinks The Role of Molecular Rigidity 420

WorldLinks Conducting Organic Polymers 421

9.2 Nomenclature of Alkynes 421

9.3 Acidity of Acetylene and Terminal Alkynes 423

9.4 Preparation of Alkynes 426

9.5 Reduction of Alkynes 428

9.6 Hydrohalogenation of Alkynes 431

9.7 Hydration of Alkynes 433

9.8 Halogenation of Alkynes 439

9.9 Ozonolysis of Alkynes 439

9.10 Alkylation of Terminal Alkynes 440

9.11 Synthesis Strategies 442

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10 Radical Reactions 454

10.1 Radicals 455

10.2 Common Patterns in Radical Mechanisms 460

10.3 Chlorination of Methane 463

10.4 Thermodynamic Considerations for Halogenation Reactions 467

10.5 Selectivity of Halogenation 469

10.6 Stereochemistry of Halogenation 472

10.7 Allylic Bromination 474

10.8 Atmospheric Chemistry and the Ozone Layer 477

WorldLinks Fighting Fires with Chemicals 479

10.9 Autooxidation and Antioxidants 480

BioLinks Why is an Overdose of Acetaminophen Fatal? 482

10.10 Radical Addition of HBr: Anti-Markovnikov Addition 483

10.11 Radical Polymerization 487

10.12 Radical Processes in the Petrochemical Industry 489

10.13 Halogenation as a Synthetic Technique 489

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11 Synthesis 499

11.1 One-Step Syntheses 500

11.2 Functional Group Transformations 501

11.3 Reactions That Change the Carbon Skeleton 505

BioLinks Vitamins 507

11.4 How to Approach a Synthesis Problem 508

BioLinks The Total Synthesis of Vitamin B12 512

11.5 Multi-step Synthesis and Retrosynthetic Analysis 514

WorldLinks Retrosynthetic Analysis 519

11.6 Green Chemistry 519

11.7 Practical Tips for Increasing Proficiency 520

BioLinks Total Synthesis of Taxol 521

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12 Alcohols and Phenols 529

12.1 Structure and Properties of Alcohols 530

BioLinks Chain Length as a Factor in Drug Design 534

12.2 Acidity of Alcohols and Phenols 535

12.3 Preparation of Alcohols via Substitution or Addition 538

12.4 Preparation of Alcohols via Reduction 539

12.5 Preparation of Diols 546

WorldLinks Antifreeze 547

12.6 Preparation of Alcohols via Grignard Reagents 547

12.7 Protection of Alcohols 552

12.8 Preparation of Phenols 553

12.9 Reactions of Alcohols: Substitution and Elimination 554

BioLinks Drug Metabolism 557

12.10 Reactions of Alcohols: Oxidation 559

12.11 Biological Redox Reactions 563

BioLinks Biological Oxidation of Methanol and Ethanol 565

12.12 Oxidation of Phenol 565

12.13 Synthesis Strategies 567

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13 Ethers and Epoxides; Thiols and Sulfides 585

13.1 Introduction to Ethers 586

13.2 Nomenclature of Ethers 586

13.3 Structure and Properties of Ethers 588

BioLinks Ethers as Inhalation Anesthetics 589

13.4 Crown Ethers 590

WorldLinks Chelating Agents in the Food Industry and in Medicine 592

13.5 Preparation of Ethers 593

13.6 Reactions of Ethers 596

13.7 Nomenclature of Epoxides 599

BioLinks Epothilones as Novel Anticancer Agents 600

13.8 Preparation of Epoxides 600

BioLinks Active Metabolites and Drug Interactions 603

13.9 Enantioselective Epoxidation 603

13.10 Ring-Opening Reactions of Epoxides 605

WorldLinks Ethylene Oxide as a Sterilizing Agent for Sensitive Medical Equipment 608

BioLinks Cigarette Smoke and Carcinogenic Epoxides 612

13.11 Thiols and Sulfides 613

13.12 Synthesis Strategies Involving Epoxides 617

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14 Infrared Spectroscopy and Mass Spectrometry 636

14.1 Introduction to Spectroscopy 637

WorldLinks Microwave Ovens 639

14.2 IR Spectroscopy 639

BioLinks IR Thermal Imaging for Cancer Detection 640

14.3 Signal Characteristics: Wavenumber 641

14.4 Signal Characteristics: Intensity 646

WorldLinks IR Spectroscopy for Testing Blood Alcohol Levels 648

14.5 Signal Characteristics: Shape 648

14.6 Analyzing an IR Spectrum 652

14.7 Using IR Spectroscopy to Distinguish between Two Compounds 657

14.8 Introduction to Mass Spectrometry 658

WorldLinks Mass Spectrometry for Detecting Explosives 660

14.9 Analyzing the (M)^+• Peak 661

14.10 Analyzing the (M+1)^+• Peak 662

14.11 Analyzing the (M+2)^+• Peak 664

14.12 Analyzing the Fragments 665

14.13 High-Resolution Mass Spectrometry 668

14.14 Gas Chromatography–Mass Spectrometry 670

14.15 Mass Spectrometry of Large Biomolecules 671

BioLinks Medical Applications of Mass Spectrometry 671

14.16 Hydrogen Deficiency Index: Degrees of Unsaturation 672

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15 Nuclear Magnetic Resonance Spectroscopy 684

15.1 Introduction to NMR Spectroscopy 685

15.2 Acquiring a ¹H NMR Spectrum 687

15.3 Characteristics of a ¹H NMR Spectrum 688

15.4 Number of Signals 689

15.5 Chemical Shift 695

15.6 Integration 702

15.7 Multiplicity 705

15.8 Drawing the Expected ¹H NMR Spectrum of a Compound 713

15.9 Using ¹H NMR Spectroscopy to Distinguish between Compounds 715

BioLinks Detection of Impurities in Heparin Sodium Using ¹H NMR Spectroscopy 717

15.10 Analyzing a ¹H NMR Spectrum 718

15.11 Acquiring a ¹³C NMR Spectrum 721

15.12 Chemical Shifts in ¹³C NMR Spectroscopy 721

15.13 DEPT ¹³C NMR Spectroscopy 724

BioLinks Magnetic Resonance Imaging (MRI) 727

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16 Conjugated Pi Systems and Pericyclic Reactions 738

16.1 Classes of Dienes 739

16.2 Conjugated Dienes 740

16.3 Molecular Orbital Theory 742

16.4 Electrophilic Addition 746

16.5 Thermodynamic Control vs. Kinetic Control 749

WorldLinks Natural and Synthetic Rubbers 752

16.6 An Introduction to Pericyclic Reactions 753

16.7 Diels–Alder Reactions 754

16.8 MO Description of Cycloadditions 760

16.9 Electrocyclic Reactions 763

16.10 Sigmatropic Rearrangements 768

BioLinks The Photoinduced Biosynthesis of Vitamin D 770

16.11 UV-Vis Spectroscopy 771

WorldLinks Sunscreens 775

16.12 Color 776

WorldLinks Bleach 777

16.13 Chemistry of Vision 777

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17 Aromatic Compounds 788

17.1 Introduction to Aromatic Compounds 789

WorldLinks What is Coal? 790

17.2 Nomenclature of Benzene Derivatives 790

17.3 Structure of Benzene 793

17.4 Stability of Benzene 794

WorldLinks Molecular Cages 798

17.5 Aromatic Compounds Other Than Benzene 801

BioLinks The Development of Nonsedating Antihistamines 806

17.6 Reactions at the Benzylic Position 808

17.7 Reduction of Benzene and Its Derivatives 813

17.8 Spectroscopy of Aromatic Compounds 815

WorldLinks Buckyballs and Nanotubes 818

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18 Aromatic Substitution Reactions 828

18.1 Introduction to Electrophilic Aromatic Substitution 829

18.2 Halogenation 829

BioLinks Halogenation in Drug Design 832

18.3 Sulfonation 833

WorldLinks What Are Those Colors in Fruity Pebbles? 834

18.4 Nitration 835

BioLinks The Discovery of Prodrugs 837

18.5 Friedel–Crafts Alkylation 838

18.6 Friedel–Crafts Acylation 840

18.7 Activating Groups 842

18.8 Deactivating Groups 846

18.9 Halogens: The Exception 848

18.10 Determining the Directing Effects of a Substituent 850

18.11 Multiple Substituents 853

18.12 Synthesis Strategies 859

18.13 Nucleophilic Aromatic Substitution 866

18.14 Elimination-Addition 868

18.15 Identifying the Mechanism of an Aromatic Substitution Reaction 870

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19 Aldehydes and Ketones 884

19.1 Introduction to Aldehydes and Ketones 885

19.2 Nomenclature 886

19.3 Preparing Aldehydes and Ketones: A Review 888

19.4 Introduction to Nucleophilic Addition Reactions 889

19.5 Oxygen Nucleophiles 892

BioLinks Acetals as Prodrugs 898

19.6 Nitrogen Nucleophiles 900

WorldLinks Beta-Carotene and Vision 904

19.7 Hydrolysis of Acetals, Imines, and Enamines 908

BioLinks Prodrugs 911

19.8 Sulfur Nucleophiles 911

19.9 Hydrogen Nucleophiles 912

19.10 Carbon Nucleophiles 913

WorldLinks Organic Cyanide Compounds in Nature 916

19.11 Baeyer–Villiger Oxidation of Aldehydes and Ketones 921

19.12 Synthesis Strategies 922

19.13 Spectroscopic Analysis of Aldehydes and Ketones 925

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20 Carboxylic Acids and Their Derivatives 938

20.1 Introduction to Carboxylic Acids 939

20.2 Nomenclature of Carboxylic Acids 939

20.3 Structure and Properties of Carboxylic Acids 941

20.4 Preparation of Carboxylic Acids 944

20.5 Reactions of Carboxylic Acids 945

20.6 Introduction to Carboxylic Acid Derivatives 946

BioLinks Sedatives 948

20.7 Reactivity of Carboxylic Acid Derivatives 950

20.8 Preparation and Reactions of Acid Chlorides 957

20.9 Preparation and Reactions of Acid Anhydrides 962

BioLinks How Does Aspirin Work? 964

20.10 Preparation of Esters 965

20.11 Reactions of Esters 966

WorldLinks How Soap is Made 967

BioLinks Esters as Prodrugs 968

20.12 Preparation and Reactions of Amides 971

WorldLinks Polyesters and Polyamides 972

BioLinks Beta-Lactam Antibiotics 975

20.13 Preparation and Reactions of Nitriles 976

20.14 Synthesis Strategies 979

20.15 Spectroscopy of Carboxylic Acids and Their Derivatives 984

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21 Alpha Carbon Chemistry: Enols and Enolates 996

21.1 Introduction to Alpha Carbon Chemistry: Enols and Enolates 997

21.2 Alpha Halogenation of Enols and Enolates 1004

21.3 Aldol Reactions 1009

WorldLinks Muscle Power 1012

21.4 Claisen Condensations 1020

21.5 Alkylation of the Alpha Position 1022

21.6 Conjugate Addition Reactions 1031

BioLinks Glutathione Conjugation and Biological Michael Reactions 1033

21.7 Synthesis Strategies 1037

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22 Amines 1054

22.1 Introduction to Amines 1055

BioLinks Drug Metabolism Studies 1056

22.2 Nomenclature of Amines 1056

22.3 Properties of Amines 1059

BioLinks Fortunate Side Effects 1060

WorldLinks Chemical Warfare Among Ants 1064

22.4 Preparation of Amines: A Review 1065

22.5 Preparation of Amines via Substitution Reactions 1066

22.6 Preparation of Amines via Reductive Amination 1069

22.7 Synthesis Strategies 1071

22.8 Acylation of Amines 1074

22.9 Hofmann Elimination 1075

22.10 Reactions of Amines with Nitrous Acid 1078

22.11 Reactions of Aryl Diazonium Ions 1080

22.12 Nitrogen Heterocycles 1084

BioLinks H₂-Receptor Antagonists and the Development of Cimetidine 1085

22.13 Spectroscopy of Amines 1087

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23 Introduction to Organometallic Compounds 1100

23.1 General Properties of Organometallic Compounds 1101

23.2 Organolithium and Organomagnesium Compounds 1102

23.3 Lithium Dialkyl Cuprates (Gilman Reagents) 1105

23.4 The Simmons–Smith Reaction and Carbenoids 1109

23.5 Stille Coupling 1112

23.6 Suzuki Coupling 1117

23.7 Negishi Coupling 1123

23.8 The Heck Reaction 1128

23.9 Alkene Metathesis 1133

WorldLinks Improving Biodiesel via Alkene Metathesis 1138

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24 Carbohydrates 1153

24.1 Introduction to Carbohydrates 1154

24.2 Classification of Monosaccharides 1154

24.3 Configuration of Aldoses 1157

24.4 Configuration of Ketoses 1158

24.5 Cyclic Structures of Monosaccharides 1160

24.6 Reactions of Monosaccharides 1167

24.7 Disaccharides 1174

BioLinks Lactose Intolerance 1177

WorldLinks Artificial Sweeteners 1178

24.8 Polysaccharides 1179

24.9 Amino Sugars 1180

24.10 N-Glycosides 1181

BioLinks Aminoglycoside Antibiotics 1182

BioLinks Erythromycin Biosynthesis 1186

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25 Amino Acids, Peptides, and Proteins 1194

25.1 Introduction to Amino Acids, Peptides, and Proteins 1195

25.2 Structure and Properties of Amino Acids 1196

WorldLinks Nutrition and Sources of Amino Acids 1198

WorldLinks Forensic Chemistry and Fingerprint Detection 1202

25.3 Amino Acid Synthesis 1203

25.4 Structure of Peptides 1207

BioLinks Polypeptide Antibiotics 1212

25.5 Sequencing a Peptide 1213

25.6 Peptide Synthesis 1216

25.7 Protein Structure 1224

BioLinks Diseases Caused by Misfolded Proteins 1227

25.8 Protein Function 1227

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26 Lipids 1238

26.1 Introduction to Lipids 1239

26.2 Waxes 1240

26.3 Triglycerides 1241

26.4 Reactions of Triglycerides 1244

WorldLinks Soaps Versus Synthetic Detergents 1249

26.5 Phospholipids 1253

BioLinks Polyether Antibiotics 1256

26.6 Steroids 1257

BioLinks Cholesterol and Heart Disease 1260

BioLinks Anabolic Steroids and Competitive Sports 1263

26.7 Prostaglandins 1263

BioLinks NSAIDs and COX-2 Inhibitors 1265

26.8 Terpenes 1266

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27 Synthetic Polymers 1277

27.1 Introduction to Synthetic Polymers 1278

27.2 Nomenclature of Synthetic Polymers 1279

27.3 Copolymers 1280

27.4 Polymer Classification by Reaction Type 1281

27.5 Polymer Classification by Mode of Assembly 1289

27.6 Polymer Classification by Structure 1291

27.7 Polymer Classification by Properties 1294

WorldLinks Safety Glass and Car Windshields 1295

27.8 Polymer Recycling 1296

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Appendix: Nomenclature of Polyfunctional Compounds A–1

Selected Answers ANS–1

Glossary G–1

Index I–1