Test Bank for Introduction to Organic Chemistry, 4th Edition: Brown

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Product details:

• ISBN-10 ‏ : ‎ 0470129239
• ISBN-13 ‏ : ‎ 978-0470129234
• Author: William H. Brown (Author), Thomas Poon (Author)

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.

Table of contents:

1 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 of Molecules? 13

1.4 How Do We Predict If a Molecule Is Polar or Nonpolar? 17

1.5 What Is Resonance? 18

1.6 What Is the Orbital Overlap Model of Covalent Bonding? 21

1.7 What Are Functional Groups? 26

Summary of Key Questions 31

Quick Quiz 32

Problems 34

Real World Problems 37

Looking Ahead 38

Group Learning Activities 39

Chemical Connections

1A Buckyball: A New Form of Carbon 16

2 Acids and Bases 40

2.1 What Are Arrhenius Acids and Bases? 41

2.2 What Are Bronsted–Lowry Acids and Bases? 42

2.3 How Do We Measure the Strength of an Acid or Base? 44

2.4 How Do We Determine the Position of Equilibrium in an Acid–Base Reaction? 46

2.5 What Are the Relationships between Acidity and Molecular Structure? 48

2.6 What Are Lewis Acids and Bases? 52

Summary of Key Questions 55

Quick Quiz 56

Key Reactions 57

Problems 57

Real World Problems 59

Looking Ahead 59

Group Learning Activities 60

3 Alkanes and Cycloalkanes 61

3.1 What Are Alkanes? 62

3.2 What Is Constitutional Isomerism in Alkanes? 64

3.3 How Do We Name Alkanes? 66

3.4 What Are Cycloalkanes? 71

3.5 How Is the IUPAC System of Nomenclature Applied to Molecules that Contain Functional Groups? 72

3.6 What Are the Conformations of Alkanes and Cycloalkanes? 73

3.7 What Is Cis–Trans Isomerism in Cycloalkanes? 80

3.8 What Are the Physical Properties of Alkanes and Cycloalkanes? 84

3.9 What Are the Characteristic Reactions of Alkanes? 87

3.10 What Are the Sources of Alkanes? 88

Summary of Key Questions 91

Quick Quiz 92

Key Reactions 93

Problems 93

Real World Problems 97

Looking Ahead 98

Group Learning Activities 99

Putting it Together 99

Chemical Connections

3A The Poisonous Puffer Fish 81

3B Octane Rating: What Those Numbers at the Pump Mean 90

4 Alkenes and Alkynes 103

4.1 What Are the Structures and Shapes of Alkenes and Alkynes? 105

4.2 How Do We Name Alkenes and Alkynes? 107

4.3 What Are the Physical Properties of Alkenes and Alkynes? 115

4.4 Why Are 1-Alkynes (Terminal Alkynes) Weak Acids? 116

Summary of Key Questions 117

Quick Quiz 118

Problems 118

Real World Problems 121

Looking Ahead 122

Group Learning Activities 122

Chemical Connections

4A Ethylene, a Plant Growth Regulator 104

4B Cis–Trans Isomerism in Vision 106

4C Why Plants Emit Isoprene 115

5 Reactions of Alkenes and Alkynes 123

5.1 What Are the Characteristic Reactions of Alkenes? 123

5.2 What Is a Reaction Mechanism? 124

5.3 What Are the Mechanisms of Electrophilic Additions to Alkenes? 130

5.4 What Are Carbocation Rearrangements? 140

5.5 What Is Hydroboration–Oxidation of an Alkene? 143

5.6 How Can an Alkene Be Reduced to an Alkane? 145

5.7 How Can an Acetylide Anion Be Used to Create a New Carbon–Carbon Bond? 148

5.8 How Can Alkynes Be Reduced to Alkenes and Alkanes? 150

Summary of Key Questions 151

Quick Quiz 152

Key Reactions 153

Problems 154

Chemical Transformation 157

Real World Problems 158

Looking Ahead 158

Group Learning Activities 159

Chemical Connections

5A Catalytic Cracking and the Importance of Alkenes 127

6 Chirality: The Handedness of Molecules 160

6.1 What Are Stereoisomers? 161

6.2 What Are Enantiomers? 161

6.3 How Do We Designate the Configuration of a Stereocenter? 166

6.4 What Is the 2n Rule? 168

6.5 How Do We Describe the Chirality of Cyclic Molecules with Two Stereocenters? 172

6.6 How Do We Describe the Chirality of Molecules with Three or More Stereocenters? 174

6.7 What Are the Properties of Stereoisomers? 174

6.8 How Is Chirality Detected in the Laboratory? 175

6.9 What Is the Significance of Chirality in the Biological World? 176

6.10 How Can Enantiomers Be Resolved? 177

Summary of Key Questions 179

Quick Quiz 180

Problems 181

Chemical Transformations 184

Real World Problems 185

Looking Ahead 186

Group Learning Activities 187

Putting it Together 187

Chemical Connections

6A Chiral Drugs 178

7 Haloalkanes 190

7.1 How Are Haloalkanes Named? 191

7.2 What Are the Characteristic Reactions of Haloalkanes? 193

7.3 What Are the Products of Nucleophilic Aliphatic Substitution Reactions? 195

7.4 What Are the S_N2 and S_N1 Mechanisms for Nucleophilic Substitution? 197

7.5 What Determines Whether S_N1 or S_N2 Predominates? 201

7.6 How Can S_N1 and S_N2 Be Predicted Based on Experimental Conditions? 206

7.7 What Are the Products of β?Elimination? 208

7.8 What Are the E1 and E2 Mechanisms for β?Elimination? 211

7.9 When Do Nucleophilic Substitution and β?Elimination Compete? 214

Summary of Key Questions 217

Quick Quiz 218

Key Reactions 218

Problems 219

Chemical Transformations 223

Looking Ahead 224

Group Learning Activities 225

Chemical Connections

7A The Environmental Impact of Chlorofluorocarbons 193

7B The Effect of Chlorofluorocarbon Legislation on Asthma Sufferers 216

8 Alcohols, Ethers, and Thiols 226

8.1 What Are Alcohols? 227

8.2 What Are the Characteristic Reactions of Alcohols? 232

8.3 What Are Ethers? 245

8.4 What Are Epoxides? 249

8.5 What Are Thiols? 253

8.6 What Are the Characteristic Reactions of Thiols? 256

Summary of Key Questions 257

Quick Quiz 258

Key Reactions 259

Problems 260

Chemical Transformations 263

Real World Problems 264

Looking Ahead 264

Group Learning Activities 265

Chemical Connections

8A Nitroglycerin: An Explosive and a Drug 230

8B Blood Alcohol Screening 245

8C Ethylene Oxide: A Chemical Sterilant 253

9 Benzene and Its Derivatives 266

9.1 What Is the Structure of Benzene? 267

9.2 What Is Aromaticity? 270

9.3 How Are Benzene Compounds Named, and What Are Their Physical Properties? 273

9.4 What Is a Benzylic Position, and How Does It Contribute to Benzene Reactivity? 276

9.5 What Is Electrophilic Aromatic Substitution? 278

9.6 What Is the Mechanism of Electrophilic Aromatic Substitution? 279

9.7 How Do Existing Substituents on Benzene Affect Electrophilic Aromatic Substitution? 288

9.8 What Are Phenols? 296

Summary of Key Questions 303

Quick Quiz 304

Key Reactions 304

Problems 305

Chemical Transformations 309

Real World Problems 310

Looking Ahead 311

Group Learning Activities 312

Chemical Connections

9A Carcinogenic Polynuclear Aromatics and Cancer 277

9B Capsaicin, for Those Who Like It Hot 300

10 Amines 313

10.1 What Are Amines? 313

10.2 How Are Amines Named? 316

10.3 What Are the Characteristic Physical Properties of Amines? 319

10.4 What Are the Acid–Base Properties of Amines? 321

10.5 What Are the Reactions of Amines with Acids? 325

10.6 How Are Arylamines Synthesized? 327

10.7 How Do Amines Act as Nucleophiles? 328

Summary of Key Questions 330

Quick Quiz 331

Key Reactions 331

Problems 332

Chemical Transformations 334

Real World Problems 335

Looking Ahead 337

Group Learning Activities 337

Putting it Together 338

Chemical Connections

10A Morphine as a Clue in the Design and Discovery of Drugs 314

10B The Poison Dart Frogs of South America: Lethal Amines 319

11 Spectroscopy 341

11.1 What Is Electromagnetic Radiation? 342

11.2 What Is Molecular Spectroscopy? 344

11.3 What Is Infrared Spectroscopy? 344

11.4 How Do We Interpret Infrared Spectra? 347

11.5 What Is Nuclear Magnetic Resonance? 358

11.6 What Is Shielding? 360

11.7 What Is a ¹H-NMR Spectrum? 360

11.8 How Many Resonance Signals Will a Compound Yield in Its ¹H?NMR Spectrum? 362

11.9 What Is Signal Integration? 365

11.10 What Is Chemical Shift? 366

11.11 What Is Signal Splitting? 368

11.12 What Is ¹³C?NMR Spectroscopy, and How Does It Differ from ¹H?NMR Spectroscopy? 371

11.13 How Do We Solve an NMR Problem? 374

Summary of Key Questions 378

Quick Quiz 380

Problems 381

Real World Problems 393

Looking Ahead 394

Group Learning Activities 395

Chemical Connections

11A Infrared Spectroscopy: A Window on Brain Activity 348

11B Infrared Spectroscopy: A Window on Climate Change 354

11C Magnetic Resonance Imaging (MRI) 371

12 Aldehydes and Ketones 396

12.1 What Are Aldehydes and Ketones? 397

12.2 How Are Aldehydes and Ketones Named? 397

12.3 What Are the Physical Properties of Aldehydes and Ketones? 401

12.4 What Is the Most Common Reaction Theme of Aldehydes and Ketones? 402

12.5 What Are Grignard Reagents, and How Do They React with Aldehydes and Ketones? 402

12.6 What Are Hemiacetals and Acetals? 407

12.7 How Do Aldehydes and Ketones React with Ammonia and Amines? 413

12.8 What Is Keto?Enol Tautomerism? 417

12.9 How Are Aldehydes and Ketones Oxidized? 420

12.10 How Are Aldehydes and Ketones Reduced? 423

Summary of Key Questions 425

Quick Quiz 426

Key Reactions 427

Problems 428

Chemical Transformations 431

Spectroscopy 432

Real World Problems 433

Looking Ahead 435

Group Learning Activities 436

Chemical Connections

12A A Green Synthesis of Adipic Acid 422

13 Carboxylic Acids 437

13.1 What Are Carboxylic Acids? 437

13.2 How Are Carboxylic Acids Named? 438

13.3 What Are the Physical Properties of Carboxylic Acids? 441

13.4 What Are the Acid–Base Properties of Carboxylic Acids? 442

13.5 How Are Carboxyl Groups Reduced? 446

13.6 What Is Fischer Esterification? 449

13.7 What Are Acid Chlorides? 453

13.8 What Is Decarboxylation? 455

Summary of Key Questions 459

Quick Quiz 459

Key Reactions 460

Problems 461

Chemical Transformations 464

Real World Problems 464

Looking Ahead 467

Group Learning Activities 467

Chemical Connections

13A From Willow Bark to Aspirin and Beyond 446

13B Esters as Flavoring Agents 451

13C Ketone Bodies and Diabetes 456

14 Functional Derivatives of Carboxylic Acids 468

14.1 What Are Some Derivatives of Carboxylic Acids, and How Are They Named? 469

14.2 What Are the Characteristic Reactions of Carboxylic Acid Derivatives? 474

14.3 What Is Hydrolysis? 475

14.4 How Do Carboxylic Acid Derivatives React with Alcohols? 480

14.5 How Do Carboxylic Acid Derivatives React with Ammonia and Amines? 483

14.6 How Can Functional Derivatives of Carboxylic Acids Be Interconverted? 485

14.7 How Do Esters React with Grignard Reagents? 486

14.8 How Are Derivatives of Carboxylic Acids Reduced? 488

Summary of Key Questions 492

Quick Quiz 493

Key Reactions 493

Problems 495

Chemical Transformations 498

Real World Problems 498

Looking Ahead 501

Group Learning Activities 501

Putting it Together 501

Chemical Connections

14A Ultraviolet Sunscreens and Sunblocks 470

14B From Moldy Clover to a Blood Thinner 471

14C The Penicillins and Cephalosporins: β?Lactam Antibiotics 472

14D The Pyrethrins: Natural Insecticides of Plant Origin 482

14E Systematic Acquired Resistance in Plants 485

15 Enolate Anions 504

15.1 What Are Enolate Anions, and How Are They Formed? 505

15.2 What Is the Aldol Reaction? 508

15.3 What Are the Claisen and Dieckmann Condensations? 515

15.4 How Are Aldol Reactions and Claisen Condensations Involved in Biological Processes? 522

15.5 What Is the Michael Reaction? 524

Summary of Key Questions 531

Quick Quiz 531

Key Reactions 532

Problems 533

Chemical Transformations 536

Real World Problems 537

Looking Ahead 540

Group Learning Activities 541

Chemical Connections

15A Drugs That Lower Plasma Levels of Cholesterol 523

15B Antitumor Compounds: The Michael Reaction in Nature 530

16 Organic Polymer Chemistry 542

16.1 What Is the Architecture of Polymers? 543

16.2 How Do We Name and Show the Structure of a Polymer? 543

16.3 What Is Polymer Morphology? Crystalline versus Amorphous Materials 545

16.4 What Is Step?Growth Polymerization? 546

16.5 What Are Chain?Growth Polymers? 551

16.6 What Plastics Are Currently Recycled in Large Quantities? 557

Summary of Key Questions 558

Quick Quiz 559

Key Reactions 560

Problems 560

Real World Problem 562

Looking Ahead 562

Group Learning Activities 562

Chemical Connections

16A Stitches That Dissolve 551

16B Paper or Plastic? 553

17 Carbohydrates 563

17.1 What Are Carbohydrates? 563

17.2 What Are Monosaccharides? 564

17.3 What Are the Cyclic Structures of Monosaccharides? 568

17.4 What Are the Characteristic Reactions of Monosaccharides? 573

17.5 What Are Disaccharides and Oligosaccharides? 577

17.6 What Are Polysaccharides? 581

Summary of Key Questions 583

Quick Quiz 584

Key Reactions 585

Problems 586

Real World Problems 588

Looking Ahead 590

Group Learning Activities 591

Putting it Together 591

Chemical Connections

17A Relative Sweetness of Carbohydrate and Artificial Sweeteners 578

17B A, B, AB, and O Blood?Group Substances 579

18 Amino Acids and Proteins 595

18.1 What Are the Many Functions of Proteins? 595

18.2 What Are Amino Acids? 596

18.3 What Are the Acid–Base Properties of Amino Acids? 599

18.4 What Are Polypeptides and Proteins? 606

18.5 What Is the Primary Structure of a Polypeptide or Protein? 607

18.6 What Are the Three?Dimensional Shapes of Polypeptides and Proteins? 611

Summary of Key Questions 618

Quick Quiz 619

Key Reactions 620

Problems 620

Real World Problems 622

Looking Ahead 623

Group Learning Activities 623

Chemical Connections

18A Spider Silk: A Chemical and Engineering Wonder of Nature 616

19 Lipids (Online Chapter) 624

19.1 What Are Triglycerides? 624

19.2 What Are Soaps and Detergents? 628

19.3 What Are Phospholipids? 630

19.4 What Are Steroids? 632

19.5 What Are Prostaglandins? 637

19.6 What Are Fat?Soluble Vitamins? 640

Summary of Key Questions 643

Quick Quiz 644

Problems 644

Real World Problems 646

Looking Ahead 646

Group Learning Activities 647

Chemical Connections

19A Snake Venom Phospholipases 632

19B Nonsteroidal Estrogen Antagonists 636

20 Nucleic Acids (Online Chapter) 648

20.1 What Are Nucleosides and Nucleotides? 648

20.2 What Is the Structure of DNA? 652

20.3 What Are Ribonucleic Acids (RNA)? 658

20.4 What Is the Genetic Code? 660

20.5 How Is DNA Sequenced? 662

Summary of Key Questions 667

Quick Quiz 668

Problems 669

Real World Problems 671

Group Learning Activities 671

Chemical Connections

20A The Search for Antiviral Drugs 650

20B DNA Fingerprinting 666

21 The Organic Chemistry of Metabolism (Online Chapter) 672

21.1 What Are the Key Participants in Glycolysis, the β?Oxidation of Fatty Acids, and the Citric Acid Cycle? 673

21.2 What Is Glycolysis? 678

21.3 What Are the Ten Reactions of Glycolysis? 678

21.4 What Are the Fates of Pyruvate? 683

21.5 What Are the Reactions of the β?Oxidation of Fatty Acids? 685

21.6 What Are the Reactions of the Citric Acid Cycle? 689

Summary of Key Questions 692

Quick Quiz 693

Key Reactions 693

Problems 694

Real World Problems 695

Group Learning Activities 696

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

Characteristic ¹H?NMR Chemical Shifts A.1

Appendix 2 Characteristic ¹³C?NMR Chemical Shifts A.2

Characteristic Infrared Absorption Frequencies A.2

Glossary G.1

Answers Section Ans.1

Index I.1

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