Introduction to Organic Chemistry / Edition 5

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This text 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.

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Product Details

  • ISBN-13: 9781118083383
  • Publisher: Wiley
  • Publication date: 12/26/2012
  • Edition description: New Edition
  • Edition number: 5
  • Pages: 792
  • Sales rank: 340,727
  • Product dimensions: 8.50 (w) x 11.00 (h) x 1.20 (d)

Meet the Author

William H. Brown is Professor Emeritus at Beloit College,where he was twice named Teacher of the Year. He is also the authorof two other college textbooks: Organic Chemistry 5/e,coauthored with Chris Foote, Brent Iverson, and Eric Anslyn,published in 2009, and General, Organic, and Biochemistry9/e, coauthored with Fred Bettelheim, Mary Campbell, and ShawnFarrell, published in 2010. He received his Ph.D. from ColumbiaUniversity under the direction of Gilbert Stork and didpostdoctoral work at California Institute of Technology and theUniversity of Arizona. Twice he was Director of a Beloit CollegeWorld Affairs Center seminar at the University of Glasgow,Scotland. In 1999, he retired from Beloit College to devote moretime to writing and development of educational materials. Althoughofficially retired, he continues to teach Special Topics in OrganicSynthesis on a yearly basis. Bill and his wife Carolyn enjoy hikingin the canyon country of the Southwest. In addition, they bothenjoy quilting and quilts.

Thomas Poon is Associate Professor of Chemistry in theJoint Science Department of Claremont McKenna, Pitzer, and ScrippsColleges, three of the five undergraduate institutions that make upthe Claremont Colleges in Claremont, California. He received hisB.S. degree from Fairfield University (CT) and his Ph.D. from theUniversity of California, Los Angeles under the direction ofChristopher S. Foote. Poon was a Camille and Henry DreyfusPostdoctoral Fellow under Bradford P. Mundy at Colby College (ME)before joining the faculty at Randolph-Macon College (VA) where hereceived the Thomas Branch Award for Excellence in Teaching in1999. He was a visiting scholar at Columbia University (NY) in 2002(and again in 2004) where he worked on projects in both researchand education with his friend and mentor, Nicholas J. Turro. He hastaught organic chemistry, forensic chemistry, upper-level coursesin advanced laboratory techniques, and a first-year seminar classtitled Science of Identity. His favorite activity is workingalongside undergraduates in the laboratory on research problemsinvolving the investigation of synthetic methodology in zeolites,zeolite photochemistry, natural products isolation, and reactionsof singlet oxygen. When not in the lab, he likes to play guitar andsing funny chemistry songs to his daughter Sophie.

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Table of Contents

01 Covalent Bonding and Shapes of Molecules 1

1.1 How Do We Describe the Electronic Structure of Atoms?2

1.2 What Is the Lewis Model of Bonding? 5

1.3 How Do We Predict Bond Angles and the Shapes ofMolecules? 14

1.4 How Do We Predict If a Molecule Is Polar or Nonpolar?18

1.5 What Is Resonance? 19

1.6 What Is the Orbital Overlap Model of CovalentBonding? 22

1.7 What Are Functional Groups? 28

Summary of Key Questions 32

Quick Quiz 34

Problems 35

Looking Ahead 40

Group Learning Activities 40


1A Buckyball: A New Form of Carbon 17

02 Acids and Bases 41

2.1 What Are Arrhenius Acids and Bases? 42

2.2 What Are Brønsted–Lowry Acids and Bases?43

2.3 How Do We Measure the Strength of an Acid or Base?46

2.4 How Do We Determine the Position of Equilibrium in anAcid–Base Reaction? 48

2.5 What Are the Relationships between Acidity andMolecular Structure? 50

2.6 What Are Lewis Acids and Bases? 54

Summary of Key Questions 57

Quick Quiz 58

Key Reactions 59

Problems 59

Looking Ahead 62

Group Learning Activities 62

03 Alkanes and Cycloalkanes 63

3.1 What Are Alkanes? 64

3.2 What Is Constitutional Isomerism in Alkanes?66

3.3 How Do We Name Alkanes? 69

3.4 What Are Cycloalkanes? 73

3.5 What Is the IUPAC System of Nomenclature?75

3.6 What Are the Conformations of Alkanes andCycloalkanes? 76

3.7 What Is Cis–Trans Isomerism inCycloalkanes? 83

3.8 What Are the Physical Properties of Alkanes andCycloalkanes? 87

3.9 What Are the Characteristic Reactions of Alkanes?91

3.10 What Are the Sources of Alkanes? 91

Summary of Key Questions 94

Quick Quiz 96

Key Reactions 97

Problems 97

Looking Ahead 102

Group Learning Activities 104

Putting It Together 104


3A The Poisonous Puffer Fish 84

3B Octane Rating: What Those Numbers at the Pump Mean94

04 Alkenes and Alkynes 108

4.1 What Are the Structures and Shapes of Alkenes andAlkynes? 110

4.2 How Do We Name Alkenes and Alkynes? 112

4.3 What Are the Physical Properties of Alkenes andAlkynes? 120

4.4 Why Are 1-Alkynes (Terminal Alkynes) Weak Acids?122

Summary of Key Questions 123

Quick Quiz 124

Problems 124

Looking Ahead 128

Group Learning Activities 128


4A Ethylene, a Plant Growth Regulator 109

4B Cis–Trans Isomerism in Vision111

4C Why Plants Emit Isoprene 121

05 Reactions of Alkenes and Alkynes 129

5.1 What Are the Characteristic Reactions of Alkenes?130

5.2 What Is a Reaction Mechanism? 130

5.3 What Are the Mechanisms of Electrophilic Additions toAlkenes? 136

5.4 What Are Carbocation Rearrangements? 147

5.5 What Is Hydroboration–Oxidation of an Alkene?150

5.6 How Can an Alkene Be Reduced to an Alkane?153

5.7 How Can an Acetylide Anion Be Used to Create a NewCarbon–Carbon Bond? 155

5.8 How Can Alkynes Be Reduced to Alkenes and Alkanes?157

Summary of Key Questions 158

Quick Quiz 159

Key Reactions 160

Problems 161

Looking Ahead 165

Group Learning Activities 166


5A Catalytic Cracking and the Importance of Alkenes133

06 Chirality: The Handedness of Molecules 167

6.1 What Are Stereoisomers? 168

6.2 What Are Enantiomers? 169

6.3 How Do We Designate the Configuration of aStereocenter? 173

6.4 What Is the 2n Rule? 176

6.5 How Do We Describe the Chirality of Cyclic Moleculeswith Two Stereocenters? 180

6.6 How Do We Describe the Chirality of Molecules withThree or More Stereocenters? 182

6.7 What Are the Properties of Stereoisomers?183

6.8 How Is Chirality Detected in the Laboratory?184

6.9 What Is the Significance of Chirality in theBiological World? 185

6.10 How Can Enantiomers Be Resolved? 186

Summary of Key Questions 189

Quick Quiz 190

Problems 191

Chemical Transformations 195

Looking Ahead 196

Group Learning Activities 196

Putting It Together 196


6A Chiral Drugs 187

07 Haloalkanes 200

7.1 How Are Haloalkanes Named? 201

7.2 What Are the Characteristic Reactions of Haloalkanes?203

7.3 What Are the Products of Nucleophilic AliphaticSubstitution Reactions? 206

7.4 What Are the SN2 and SN1 Mechanisms for NucleophilicSubstitution? 208

7.5 What Determines Whether SN1 or SN2 Predominates?211

7.6 How Can SN1 and SN2 Be Predicted Based onExperimental Conditions? 217

7.7 What Are the Products of b-Elimination?219

7.8 What Are the E1 and E2 Mechanisms for b-Elimination?222

7.9 When Do Nucleophilic Substitution and b-EliminationCompete? 225

Summary of Key Questions 229

Quick Quiz 230

Key Reactions 231

Problems 231

Chemical Transformations 236

Looking Ahead 237

Group Learning Activities 238


7A The Environmental Impact of Chlorofluorocarbons204

7B The Effect of Chlorofluorocarbon Legislation on AsthmaSufferers 228

08 Alcohols, Ethers, and Thiols 239

8.1 What Are Alcohols? 240

8.2 What Are the Characteristic Reactions of Alcohols?246

8.3 What Are Ethers? 260

8.4 What Are Epoxides? 264

8.5 What Are Thiols? 268

8.6 What Are the Characteristic Reactions of Thiols?271

Summary of Key Questions 272

Quick Quiz 274

Key Reactions 274

Problems 275

Chemical Transformations 279

Looking Ahead 280

Group Learning Activities 281


8A Nitroglycerin: An Explosive and a Drug 243

8B Blood Alcohol Screening 260

8C Ethylene Oxide: A Chemical Sterilant 268

09 Benzene and Its Derivatives 282

9.1 What Is the Structure of Benzene? 283

9.2 What Is Aromaticity? 286

9.3 How Are Benzene Compounds Named, and What Are TheirPhysical Properties? 289

9.4 What Is the Benzylic Position, and How Does ItContribute to Benzene Reactivity? 292

9.5 What Is Electrophilic Aromatic Substitution?295

9.6 What Is the Mechanism of Electrophilic AromaticSubstitution? 296

9.7 How Do Existing Substituents on Benzene AffectElectrophilic Aromatic Substitution? 305

9.8 What Are Phenols? 314

Summary of Key Questions 321

Quick Quiz 322

Key Reactions 322

Problems 324

Chemical Transformations 329

Looking Ahead 330

Group Learning Activities 330


9A Carcinogenic Polynuclear Aromatics and Cancer293

9B Capsaicin, for Those Who Like It Hot 318

10 Amines 331

10.1 What Are Amines? 333

10.2 How Are Amines Named? 334

10.3 What Are the Characteristic Physical Properties ofAmines? 337

10.4 What Are the Acid–Base Properties of Amines?340

10.5 What Are the Reactions of Amines with Acids?344

10.6 How Are Arylamines Synthesized? 346

10.7 How Do Amines Act as Nucleophiles? 347

Summary of Key Questions 349

Quick Quiz 350

Key Reactions 350

Problems 351

Chemical Transformations 356

Looking Ahead 357

Group Learning Activities 357

Putting It Together 357


10A Morphine as a Clue in the Design and Discovery ofDrugs 332

10B The Poison Dart Frogs of South America: Lethal Amines338

11 Spectroscopy 361

11.1 What Is Electromagnetic Radiation? 362

11.2 What Is Molecular Spectroscopy? 364

11.3 What Is Infrared Spectroscopy? 364

11.4 How Do We Interpret Infrared Spectra? 367

11.5 What Is Nuclear Magnetic Resonance? 378

11.6 What Is Shielding? 380

11.7 What Is an NMR Spectrum? 380

11.8 How Many Resonance Signals Will a Compound Yield inIts NMR Spectrum? 382

11.9 What Is Signal Integration? 385

11.10 What Is Chemical Shift? 386

11.11 What Is Signal Splitting? 388

11.12 What Is 13C-NMR Spectroscopy, and How Does ItDiffer from 1H-NMR Spectroscopy? 391

11.13 How Do We Solve an NMR Problem? 394

Summary of Key Questions 398

Quick Quiz 400

Problems 401

Looking Ahead 414

Group Learning Activities 415


11A Infrared Spectroscopy: A Window on Brain Activity368

11B Magnetic Resonance Imaging 391

12 Aldehydes and Ketones 416

12.1 What Are Aldehydes and Ketones? 417

12.2 How Are Aldehydes and Ketones Named? 417

12.3 What Are the Physical Properties of Aldehydes andKetones? 421

12.4 What Is the Most Common Reaction Theme of Aldehydesand Ketones? 422

12.5 What Are Grignard Reagents, and How Do They Reactwith Aldehydes and Ketones? 423

12.6 What Are Hemiacetals and Acetals? 427

12.7 How Do Aldehydes and Ketones React with Ammonia andAmines? 434

12.8 What Is Keto–Enol Tautomerism? 437

12.9 How Are Aldehydes and Ketones Oxidized?441

12.10 How Are Aldehydes and Ketones Reduced?443

Summary of Key Questions 445

Quick Quiz 447

Key Reactions 447

Problems 448

Chemical Transformations 454

Spectroscopy 455

Looking Ahead 456

Group Learning Activities 456


12A A Green Synthesis of Adipic Acid 442

13 Carboxylic Acids 457

13.1 What Are Carboxylic Acids? 458

13.2 How Are Carboxylic Acids Named? 458

13.3 What Are the Physical Properties of CarboxylicAcids? 461

13.4 What Are the Acid–Base Properties ofCarboxylic Acids? 462

13.5 How Are Carboxyl Groups Reduced? 466

13.6 What Is Fischer Esterification? 470

13.7 What Are Acid Chlorides? 473

13.8 What Is Decarboxylation? 475

Summary of Key Questions 479

Quick Quiz 480

Key Reactions 480

Problems 481

Chemical Transformations 486

Looking Ahead 487

Group Learning Activities 487


13A From Willow Bark to Aspirin and Beyond 466

13B Esters as Flavoring Agents 472

13C Ketone Bodies and Diabetes 476

14 Functional Derivatives of Carboxylic Acids 488

14.1 What Are Some Derivatives of Carboxylic Acids, andHow Are They Named? 489

14.2 What Are the Characteristic Reactions of CarboxylicAcid Derivatives? 495

14.3 What Is Hydrolysis? 496

14.4 How Do Carboxylic Acid Derivatives React withAlcohols? 501

14.5 How Do Carboxylic Acid Derivatives React withAmmonia and Amines? 503

14.6 How Can Functional Derivatives of Carboxylic AcidsBe Interconverted? 505

14.7 How Do Esters React with Grignard Reagents?507

14.8 How Are Derivatives of Carboxylic Acids Reduced?509

Summary of Key Questions 513

Quick Quiz 514

Key Reactions 515

Problems 516

Chemical Transformations 522

Looking Ahead 523

Group Learning Activities 523

Putting It Together 523


14A Ultraviolet Sunscreens and Sunblocks 490

14B From Moldy Clover to a Blood Thinner 491

14C The Penicillins and Cephalosporins: b-LactamAntibiotics 492

14D The Pyrethrins: Natural Insecticides of Plant Origin503

14E Systematic Acquired Resistance in Plants506

15 Enolate Anions 526

15.1 What Are Enolate Anions, and How Are They Formed?527

15.2 What Is the Aldol Reaction? 530

15.3 What Are the Claisen and Dieckmann Condensations?537

15.4 How Are Aldol Reactions and Claisen CondensationsInvolved in Biological Processes? 545

15.5 What Is the Michael Reaction? 547

Summary of Key Questions 554

Quick Quiz 554

Key Reactions 555

Problems 556

Chemical Transformations 561

Looking Ahead 562

Group Learning Activities 563


15A Drugs That Lower Plasma Levels of Cholesterol546

15B Antitumor Compounds: The Michael Reaction in Nature553

16 Organic Polymer Chemistry 564

16.1 What Is the Architecture of Polymers? 565

16.2 How Do We Name and Show the Structure of a Polymer?565

16.3 What Is Polymer Morphology? Crystalline versusAmorphous Materials 567

16.4 What Is Step-Growth Polymerization? 568

16.5 What Are Chain-Growth Polymers? 573

16.6 What Plastics Are Currently Recycled in LargeQuantities? 579

Summary of Key Questions 580

Quick Quiz 581

Key Reactions 582

Problems 582

Looking Ahead 584

Group Learning Activities 585


16A Stitches That Dissolve 573

16B Paper or Plastic? 575

17 Carbohydrates 586

17.1 What Are Carbohydrates? 586

17.2 What Are Monosaccharides? 587

17.3 What Are the Cyclic Structures of Monosaccharides?591

17.4 What Are the Characteristic Reactions ofMonosaccharides? 596

17.5 What Are Disaccharides and Oligosaccharides?601

17.6 What Are Polysaccharides? 604

Summary of Key Questions 606

Quick Quiz 608

Key Reactions 608

Problems 609

Looking Ahead 614

Group Learning Activities 614

Putting It Together 615


17A Relative Sweetness of Carbohydrate and ArtificialSweeteners 602

17B A, B, AB, and O Blood-Group Substances 603

18 Amino Acids and Proteins 619

18.1 What Are the Many Functions of Proteins?620

18.2 What Are Amino Acids? 620

18.3 What Are the Acid–Base Properties of AminoAcids? 623

18.4 What Are Polypeptides and Proteins? 630

18.5 What Is the Primary Structure of a Polypeptide orProtein? 631

18.6 What Are the Three-Dimensional Shapes ofPolypeptides and Proteins? 635

Summary of Key Questions 642

Quick Quiz 643

Key Reactions 644

Problems 645

Looking Ahead 648

Group Learning Activities 648


18A Spider Silk: A Chemical and Engineering Wonder ofNature 640

19 Lipids 649

19.1 What Are Triglycerides? 650

19.2 What Are Soaps and Detergents? 653

19.3 What Are Phospholipids? 655

19.4 What Are Steroids? 657

19.5 What Are Prostaglandins? 662

19.6 What Are Fat-Soluble Vitamins? 665

Summary of Key Questions 668

Quick Quiz 669

Problems 669

Looking Ahead 672

Group Learning Activities 673


19A Snake Venom Phospholipases 657

19B Nonsteroidal Estrogen Antagonists 661

20 Nucleic Acids (Online Chapter) 674

20.1 What Are Nucleosides and Nucleotides? 675

20.2 What Is the Structure of DNA? 678

20.3 What Are Ribonucleic Acids (RNA)? 685

20.4 What Is the Genetic Code? 687

20.5 How Is DNA Sequenced? 689

Summary of Key Questions 694

Quick Quiz 696

Problems 696

Group Learning Activities 699


20A The Search for Antiviral Drugs 677

20B DNA Fingerprinting 694

21 The Organic Chemistry of Metabolism (Online Chapter)700

21.1 What Are the Key Participants in Glycolysis, theb-Oxidation of Fatty Acids, and the Citric Acid Cycle?701

21.2 What Is Glycolysis? 706

21.3 What Are the Ten Reactions of Glycolysis?707

21.4 What Are the Fates of Pyruvate? 711

21.5 What Are the Reactions of the b-Oxidation of FattyAcids? 713

21.6 What Are the Reactions of the Citric Acid Cycle?717

Summary of Key Questions 720

Quick Quiz 721

Key Reactions 722

Problems 722

Group Learning Activities 724

Appendix 1 Acid Ionization Constants for the Major Classes ofOrganic Acids A.1

Appendix 2 Characteristic 1H-NMR Chemical Shifts A.2

Appendix 3 Characteristic 13C-NMR Chemical Shifts A.3

Appendix 4 Characteristic Infrared Absorption FrequenciesA.4

Glossary G.1

Answers Section Ans.1

Index I.1

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