Introduction to General, Organic, and Biochemistry, 12th Edition PDF by Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar J. Torres and Sara Madsen

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Introduction to General, Organic, and Biochemistry, Twelfth Edition

By Frederick A. Bettelheim, William H. Brown, Mary K. Ca mpbell, Shaw n O. Farrell, Omar J. Torres and Sara Madsen

Introduction to General, Organic, and Biochemistry

Contents:

Chapter 1 Matter, Energy, and

Measurement 1

1.1 Chemistry and the Study of Matter 1

1.2 The Scientific Method 3

1.3 Reporting Numbers in Science 5

How To Determine the Number of Significant Figures in

a Number 6

1.4 Making Measurements 7

1.5 Unit Conversions 12

How To Do Unit Conversions by the Factor-Label

Method 13

1.6 States of Matter 17

1.7 Density and Specific Gravity 18

1.8 Describing the Various Forms of Energy 20

Chapter Summary 21

Problems 22

CHEMICAL CONNECTIONS

1A Drug Dosage and Body Mass 11

Chapter 2 Atoms 26

2.1 Composition of Matter 26

2.2 Classifying Matter 27

2.3 Postulates of Dalton’s Atomic Theory 30

2.4 Composition of Atoms 33

2.5 The Periodic Table 38

2.6 Arrangement of Electrons in an Atom 44

2.7 Electron Configuration and the Periodic Table 51

2.8 Periodic Properties 52

Chapter Summary 55

Problems 56

CHEMICAL CONNECTIONS

2A Elements Necessary for Human Life 28

2B Abundance of Elements Present in the Human Body

and in the Earth’s Crust 32

2C Strontium-90 42

2D The Use of Metals as Historical Landmarks 43

Chapter 3 Chemical Bonds 63

3.1 The Octet Rule 63

3.2 Naming Anions and Cations 66

3.3 The Two Major Types of Chemical Bonds 68

3.4 An Ionic Bond 70

3.5 Naming Ionic Compounds 72

3.6 A Covalent Bond 74

How To Draw Lewis Structures 77

3.7 Naming Binary Covalent Compounds 82

3.8 Resonance 82

How To Draw Curved Arrows and Push Electrons 84

3.9 Predicting Bond Angles in Covalent Molecules 87

3.10 Determining If a Molecule Is Polar 91

Chapter Summary 93

Problems 94

CHEMICAL CONNECTIONS

3A Coral Chemistry and Broken Bones 68

3B Ionic Compounds in Medicine 75

3C Nitric Oxide: Air Pollutant and Biological

Messenger 83

Chapter 4 Chemical

Reactions and Energy

Calculations 104

4.1 The Chemical Reaction 104

4.2 Balancing Chemical

Equations 104

How To Balance a Chemical

Equation 105

4.3 Predicting Whether Ions in

Aqueous Solution Will React

with Each Other 108

4.4 Oxidation and Reduction Reactions 112

4.5 Formula Weights and Molecular Weights 117

4.6 The Mole and Calculating Mass Relationships 117

4.7 Calculating Mass Relationships in Chemical

Reactions 121

4.8 Describing Heat and the Ways in Which It Is

Transferred 128

4.9 Heat of Reaction 131

Chapter Summary 132

Problems 133

CHEMICAL CONNECTIONS

4A Solubility and Tooth Decay 112

4B Voltaic Cells 115

4C Artificial Pacemakers and Redox 116

Chapter 5 Gases, Liquids, and Solids 140

5.1 Introduction to the Three States of Matter 140

5.2 Gas Pressure and Measurements 141

5.3 The Behavior of Gases 142

5.4 Avogadro’s Law and the Ideal Gas Law 146

5.5 Dalton’s Law of Partial Pressures 148

5.6 The Kinetic Molecular Theory 150

5.7 Types of Intermolecular Attractive Forces 151

5.8 The Behavior of Liquids at the Molecular

Level 155

Chapter Summary 161

Problems 162

CHEMICAL CONNECTIONS

5A Breathing and Boyle’s Law 143

5B Hyperbaric Medicine 149

5C Blood Pressure Measurement 157

5D The Densities of Ice and Water 160

Chapter 6 Solutions and Colloids 168

6.1 Introduction to Mixtures 168

6.2 The Most Common Types of Solutions 169

6.3 The Distinguishing Characteristics of

Solutions 169

6.4 Factors Affecting Solubility 171

6.5 The Most Common Units for Concentration 174

6.6 Water as a Good Solvent 180

6.7 Colloids 185

6.8 Colligative Properties 187

Chapter Summary 194

Problems 194

CHEMICAL CONNECTIONS

6A Acid Rain 170

6B The Bends 173

6C Electrolyte Solutions in Body and Intravenous

Fluids 181

6D Hydrates and Air Pollution: The Decay of Buildings

and Monuments 184

6E Emulsions and Emulsifying Agents 186

6F Reverse Osmosis and Desalinization 191

6G Hemodialysis 193

Chapter 7 Reaction Rates and

Chemical Equilibrium 200

7.1 Measuring Reaction Rates 200

7.2 Molecular Collisions and Reactions 202

7.3 Activation Energy and Reaction Rate 204

7.4 Rate of a Chemical Reaction 206

7.5 Equilibrium 210

7.6 The Equilibrium Constant 213

How To Interpret the Value of the Equilibrium

Constant, K 216

7.7 Le Chatelier’s Principle 218

Chapter Summary 223

Problems 224

CHEMICAL CONNECTIONS

7A Why High Fever Is Dangerous 209

7B The Effects of Lowering Body Temperature 211

7C Timed-Release Medication 212

7D Sunglasses and Le Chatelier’s Principle 221

7E The Haber Process 223

Chapter 8 Acids and Bases 229

8.1 Acids and Bases 229

8.2 Defining the Strength of Acids

and Bases 231

8.3 Conjugate Acid–Base

Pairs 233

How To Name Common Acids 235

8.4 The Position of Equilibrium in

an Acid–Base Reaction 236

8.5 Acid Ionization

Constants 238

How To Use Logs and

Antilogs 239

8.6 Properties of Acids and Bases 241

8.7 Acidic and Basic Properties of Pure Water 244

8.8 pH and pOH 246

8.9 Using Titrations to Calculate Concentration 249

8.10 Buffers 251

8.11 Calculating the pH of a Buffer 255

8.12 TRIS, HEPES, and Other Biochemical Buffers 257

Chapter Summary 260

Problems 261

Chemical Connections

8A Some Important Acids and Bases 232

8B Drugstore Antacids 245

8C Respiratory and Metabolic Acidosis 258

8D Alkalosis and the Sprinter’s Trick 260

Chapter 9 Nuclear Chemistry 266

9.1 Discovery of Radioactivity 266

9.2 Defining Radioactivity 267

9.3 Nucleus and Radioactivity 268

How To Balance a Nuclear Equation 270

9.4 Nuclear Half-Life 273

9.5 Detecting and Measuring Nuclear Radiation 276

9.6 Radiation Dosimetry and Human Health 279

9.7 Nuclear Medicine 282

9.8 Nuclear Fusion 287

9.9 Nuclear Fission and Atomic Energy 289

Chapter Summary 291

Summary of Key Reactions 292

Problems 292

CHEMICAL CONNECTIONS

9A Radioactive Dating 275

9B The Indoor Radon Problem 281

9C How Radiation Damages Tissues: Free Radicals 283

9D Magnetic Resonance Imaging 285

9E Radioactive Fallout from Nuclear Accidents 291

Chapter 10 Organic Chemistry 298

10.1 Introduction to Organic Chemistry 298

10.2 Obtaining Organic Compounds 300

10.3 Writing Structural Formulas of Organic Compounds 302

10.4 Functional Groups 304

Chapter Summary 310

Problems 310

CHEMICAL CONNECTIONS

10A Taxol: A Story of Search and Discovery 301

Chapter 11 Alkanes 316

11.1 Introduction to Alkanes 316

11.2 Writing Structural Formulas of Alkanes 317

11.3 Constitutional Isomers 318

11.4 Naming Alkanes 321

11.5 Obtaining Alkanes 325

11.6 Cycloalkanes 325

11.7 Shapes of Alkanes and Cycloalkanes 327

How To Draw Alternative Chair Conformations of

Cyclohexane 329

11.8 Cis-Trans Isomerism in Cycloalkanes 331

11.9 Physical Properties of Alkanes and

Cycloalkanes 333

11.10 Characteristic Reactions of Alkanes 336

11.11 Some Important Haloalkanes 338

Chapter Summary 339

Summary of Key Reactions 340

Problems 341

CHEMICAL CONNECTIONS

11A The Poisonous Puffer Fish 330

11B Octane Rating: What Those Numbers at the Pump Mean 336

11C The Environmental Impact of Freons 338

Chapter 12 Alkenes, Alkynes, and Aromatic

Compounds 347

12.1 Introduction to Alkenes and Alkynes 347

12.2 Structures of Alkenes and Alkynes 348

12.3 Naming Alkenes and Alkynes 349

12.4 Physical Properties of Alkenes and Alkynes 354

12.5 Characteristic Reactions of Alkenes 355

12.6 Important Polymerization Reactions of Ethylene

and Substituted Ethylenes 364

12.7 Structure of Benzene 368

12.8 Naming Aromatic Compounds 370

12.9 Reactions of Benzene and Its Derivatives 372

12.10 Phenols 374

Chapter Summary 377

Summary of Key Reactions 378

Problems 379

Chemical Connections

12A Cis-Trans Isomerism in Vision 355

12B Recycling Plastics 366

12C DDT: A Boon and a Curse 372

12D Iodide Ion and Goiter 373

12E Capsaicin, for Those Who Like It Hot 376

Chapter 13 Alcohols, Ethers, and

Thiols 388

13.1 Structures, Names, and Physical Properties of

Alcohols 389

13.2 Characteristic Reactions of

Alcohols 393

13.3 Structures, Names, and Physical

Properties of Ethers 398

13.4 Structures, Names, and Physical

Properties of Thiols 402

13.5 Commercially Important

Alcohols 404

Chapter Summary 406

Summary of Key

Reactions 407

Problems 407

CHEMICAL CONNECTIONS

13A The Importance of Hydrogen Bonding in Drug-

Receptor Interactions 394

13B Breath-Alcohol Screening 399

13C Ethylene Oxide: A Chemical Sterilant 400

13D Ethers and Anesthesia 401

Chapter 14 Chirality: The Handedness of

Molecules 413

14.1 Enantiomerism 413

How To Draw Enantiomers 417

14.2 Specifying the Configuration of a Stereocenter 419

14.3 Possible Stereoisomers for Molecules with Two or

More Stereocenters 423

14.4 Optical Activity and Chirality in the Laboratory 427

14.5 Significance of Chirality in the Biological

World 428

Chapter Summary 430

Problems 430

Chemical Connections

14A Chiral Drugs 427

Chapter 15 Amines 436

15.1 Structure of Amines 436

15.2 Names of Amines 439

15.3 Physical Properties of Amines 442

15.4 Basicity of Amines 442

15.5 Characteristic Reactions of Amines 445

Chapter Summary 449

Summary of Key Reactions 449

Problems 449

CHEMICAL CONNECTIONS

15A Amphetamines (Pep Pills) 437

15B Alkaloids 438

15C Tranquilizers 443

15D The Solubility of Drugs in Body Fluids 446

15E Epinephrine: A Prototype for the Development of

New Bronchodilators 448

Chapter 16 Aldehydes and Ketones 455

16.1 Aldehydes and Ketones 455

16.2 Naming Aldehydes and Ketones 456

16.3 Physical Properties of Aldehydes and Ketones 459

16.4 Characteristic Reactions of Aldehydes and

Ketones 460

16.5 Keto-Enol Tautomerism 467

Chapter Summary 468

Summary of Key Reactions 468

Problems 469

Chemical Connections

16A From Moldy Clover to a Blood Thinner 459

Chapter 17 Carboxylic Acids 476

17.1 Carboxylic Acids 476

17.2 Names of Carboxylic Acids 476

17.3 Physical Properties of Carboxylic Acids 480

17.4 Soaps and Detergents 481

17.5 Characteristic Reactions of Carboxylic Acids 486

Chapter Summary 494

Summary of Key Reactions 494

Problems 495

CHEMICAL CONNECTIONS

17A Trans Fatty Acids: What Are They and How Do You

Avoid Them? 483

17B Esters as Flavoring Agents 491

17C Ketone Bodies and Diabetes 493

Chapter 18 Carboxylic

Anhydrides, Esters, and

Amides 502

18.1 Carboxylic Anhydrides,

Esters, and Amides 502

18.2 Preparation of Esters 506

18.3 Preparation of Amides 507

18.4 Characteristic Reactions

of Anhydrides, Esters, and

Amides 507

18.5 Phosphoric Anhydrides and

Phosphoric Esters 515

18.6 Step-Growth Polymerization 515

Chapter Summary 518

Summary of Key Reactions 519

Problems 520

Chemical Connections

18A The Pyrethrins—Natural Insecticides of Plant

Origin 504

18B The Penicillins and Cephalosporins: b-Lactam

Antibiotics 505

18C From Willow Bark to Aspirin and Beyond 506

18D Ultraviolet Sunscreens and Sunblocks 510

18E Barbiturates 514

18F Stitches That Dissolve 518

Chapter 19 Carbohydrates 525

19.1 Monosaccharides: The Simplest

Carbohydrates 525

19.2 Cyclic Structures of Monosaccharides 531

19.3 Characteristic Reactions of Monosaccharides 534

19.4 Disaccharides and Oligosaccharides 539

19.5 Polysaccharides 544

19.6 Acidic Polysaccharides 546

Chapter Summary 548

Summary of Key Reactions 549

Problems 550

Chemical Connections

19A Galactosemia 531

19B Testing for Glucose 537

19C A, B, AB, and O Blood Types 540

19D Is There a Connection Between Carbohydrates and

Obesity? 546

Chapter 20 Lipids 555

20.1 Importance of Lipids 555

20.2 Fatty Acids 556

20.3 Triglyceride Structure 559

20.4 Properties of Triglycerides 560

20.5 Structures of Complex Lipids 564

17B Esters as Flavoring Agents 491

17C Ketone Bodies and Diabetes 493

Chapter 18 Carboxylic

Anhydrides, Esters, and

Amides 502

18.1 Carboxylic Anhydrides,

Esters, and Amides 502

18.2 Preparation of Esters 506

18.3 Preparation of Amides 507

18.4 Characteristic Reactions

of Anhydrides, Esters, and

Amides 507

18.5 Phosphoric Anhydrides and

Phosphoric Esters 515

18.6 Step-Growth Polymerization 515

Chapter Summary 518

Summary of Key Reactions 519

Problems 520

Chemical Connections

18A The Pyrethrins—Natural Insecticides of Plant

Origin 504

18B The Penicillins and Cephalosporins: b-Lactam

Antibiotics 505

18C From Willow Bark to Aspirin and Beyond 506

18D Ultraviolet Sunscreens and Sunblocks 510

18E Barbiturates 514

18F Stitches That Dissolve 518

Chapter 19 Carbohydrates 525

19.1 Monosaccharides: The Simplest

Carbohydrates 525

19.2 Cyclic Structures of Monosaccharides 531

19.3 Characteristic Reactions of Monosaccharides 534

19.4 Disaccharides and Oligosaccharides 539

19.5 Polysaccharides 544

19.6 Acidic Polysaccharides 546

Chapter Summary 548

Summary of Key Reactions 549

Problems 550

Chemical Connections

19A Galactosemia 531

19B Testing for Glucose 537

19C A, B, AB, and O Blood Types 540

19D Is There a Connection Between Carbohydrates and

Obesity? 546

Chapter 20 Lipids 555

20.1 Importance of Lipids 555

20.2 Fatty Acids 556

20.3 Triglyceride Structure 559

20.4 Properties of Triglycerides 560

20.5 Structures of Complex Lipids 564

20.6 Lipids and Membrane Structure 565

20.7 Glycerophospholipids 566

20.8 Sphingolipids 568

20.9 Glycolipids 570

20.10 Steroids 571

20.11 Physiological Roles of Steroid Hormones 578

20.12 Bile Salts 583

20.13 Prostaglandins, Thromboxanes, and

Leukotrienes 584

20.14 Molecular Transport Across Membranes 589

Chapter Summary 594

Problems 596

Chemical Connections

20A Butter vs. Margarine – Which is healthier? 562

20B Lipid Storage Diseases 572

20C Anabolic Steroids 580

20D Oral Contraception 584

20E Action of Anti-inflammatory Drugs 586

20F Why Should We Eat More Salmon? 587

Chapter 21 Proteins 600

21.1 The Many Functions of Proteins 600

21.2 Amino Acids 601

21.3 Amino Acids Exist as Zwitterions 607

21.4 Amino Acids Combine to Form Proteins 610

21.5 Amino Acid Characteristics 613

21.6 Uncommon Amino Acids 615

21.7 Protein Properties 616

21.8 Protein Primary Structure 618

21.9 Protein Secondary Structure 623

21.10 Protein Tertiary Structure 625

21.11 Protein Quaternary Structure 630

21.12 Protein Denaturation 634

Chapter Summary 636

Problems 637

Chemical Connections

21A Aspartame, the Sweet Peptide 612

21B AGE and Aging 616

21C Peptide Hormones—Small Molecules with Big

Effects 620

21D Sickle Cell Anemia 622

21E Protein/Peptide Conformation–Dependent

Diseases 632

21F Laser Surgery and Protein Denaturation 635

Chapter 22 Enzymes 641

22.1 Enzymes are Biological Catalysts 641

22.2 Enzyme Nomenclature 643

22.3 Enzyme Activity 644

22.4 Enzyme Mechanisms 647

22.5 Enzyme Regulation 655

22.6 Enzymes in Medicine 659

Chapter Summary 661

Problems 662

Chemical Connections

22A Enzymes Allow Us to Enjoy Champagne 643

22B Enzymes and Memory 649

22C Medical Uses of Inhibitors 652

22D Case Study in Enzyme Regulation 660

Chapter 23 Chemical

Communications:

Neurotransmitters and

Hormones 667

23.1 Cells Communicate in Many

Ways 667

23.2 Neurotransmitters and

Hormones 668

23.3 Cholinergic Messengers 671

23.4 Amino Acid Neurotransmitters 677

23.5 Adrenergic Messengers 679

23.6 Peptides in Chemical Communications 684

23.7 Steroid Hormone Messengers 689

23.8 Drugs Affect Chemical Communications 690

Chapter Summary 693

Problems 694

Chemical Connections

23A Zebrafish, Synapses, and Sleep 672

23B Alzheimer’s Disease and Chemical

Communication 674

23C Parkinson’s Disease: Depletion of Dopamine 683

23D Diabetes 687

23E Depression—An Epidemic In Modern Times 691

Chapter 24 Nucleotides, Nucleic Acids,

and Heredity 697

24.1 DNA and RNA are the Molecules

of Heredity 697

24.2 Nucleic Acids 698

24.3 The Structure of DNA and RNA 703

24.4 RNA Types 710

24.5 Genes 714

24.6 Medical Applications of RNA 715

24.7 DNA Replication 717

24.8 DNA Amplification 721

Chapter Summary 727

Problems 728

Chemical Connections

24A Who Owns Your Genes? 701

24B DNA Fingerprinting 709

24C Telomeres, Telomerase, and Immortality 722

24D Synthetic Genome Created 722

24E Did the Neandertals Go Extinct? 725

Chapter 25 Gene Expression and Protein

Synthesis 731

25.1 DNA Leads to RNA and Protein 731

25.2 Transcription of DNA 733

25.3 Translation of RNA 735

25.4 The Genetic Code 736

25.5 Protein Synthesis 738

25.6 Gene Regulation 746

25.7 DNA Mutations 751

25.8 DNA Manipulation 755

25.9 Gene Therapy 756

25.10 Epigenetics 760

Chapter Summary 762

Problems 763

Chemical Connections

25A Breaking the Dogma: The Twenty-First Amino

Acid 744

25B Protein Synthesis Makes Memories 744

25C Mutations and Biochemical Evolution 752

25D Silent Mutations 753

25E p53: A Central Tumor Suppressor Protein 754

25F Twenty Years of Cystic Fibrosis Trials and

Tribulations 758

25G How Cancer and Aging Are Related to Epigenetic

States 761

Chapter 26 Bioenergetics: How the Body

Converts Food to Energy 766

26.1 The Nature of Metabolism 766

26.2 Mitochondria and Their Role in Metabolism 767

26.3 The Principal Compounds of Catabolic

Pathways 770

26.4 The Citric Acid Cycle and in Metabolism 773

26.5 Electron and H1 Transport 777

26.6 The Chemiosmotic Pump and ATP Production 781

26.7 Energy Yield from Aerobic Metabolism 782

26.8 Conversion of Chemical Energy to Other

Forms 783

Chapter Summary 786

Problems 787

Chemical Connections

26A Uncoupling and Obesity 780

26B ATP in Cell Signaling 785

Chapter 27 Specific Catabolic Pathways:

Carbohydrate, Lipid, and Protein

Metabolism 790

27.1 The General Outline of Catabolic Pathway 790

27.2 The Reactions of Glycolysis 793

27.3 The Energy Yield from Glucose Catabolism 798

27.4 Glycerol Catabolism 801

27.5 b-Oxidation of Fatty Acids 802

27.6 The Energy Yield from Stearic Acid

Catabolism 805

27.7 Ketone Bodies 806

27.8 Nitrogen Processing in Amino Acid

Catabolism 809

27.9 Carbon Skeleton Processing in Amino Acid

Catabolsim 814

Chapter Summary 816

Problems 817

Chemical Connections

27A Lactate Accumulation 796

27B Treating Obesity—Changing Carbohydrate

Metabolism 800

27C Ketoacidosis in Diabetes 808

27D Hereditary Defects in Amino Acid Catabolism:

PKU 813

Chapter 28 Biosynthetic

Pathways 820

28.1 The General Outline of

Biosynthetic Pathways 820

28.2 Biosynthesis of

Carbohydrates 822

28.3 Biosynthesis of Fatty

Acids 827

28.4 Biosynthesis of Membrane Lipids 829

28.5 Biosynthesis of Amino Acids 832

Chapter Summary 835

Problems 835

Chemical Connections

28A Photosynthesis 823

28B Acetyl-CoA Carboxylase—A New Target in the Fight

Against Obesity 828

28C Statin Drugs as Inhibitors of Cholesterol

Biosynthesis 831

28D Essential Amino Acids 833

Chapter 29 Nutrition 838

29.1 Nutritional Guidelines 838

29.2 Counting Calories 843

29.3 Carbohydrate Digestion 845

29.4 Fat Digestion 847

29.5 Protein Digestion 848

29.6 The Importance of Vitamins, Minerals, and

Water 850

Chapter Summary 860

Problems 861

Chemical Connections

29A The New Food Guide 841

29B Why Is It So Hard to Lose Weight? 844

29C Do Hormones or Overeating Cause Obesity? 846

29D Iron: An Example of a Mineral Requirement 856

29E Food for Performance Enhancement 857

29F Depression in America—Don’t Worry; Be

Happy 858

29G Is Gluten-Freedom a Fad? 859

Chapter 30 Immunochemistry 864

30.1 The Body’s Defense against Invasion 864

30.2 Organs and Cells of the Immune System 866

30.3 Antigens Stimulate the Immune System 870

30.4 Immunoglobulins 872

30.5 T Cells and T-Cell Receptors 878

30.6 Immunization 880

30.7 Distinguishing “Self” from “Nonself” 884

30.8 The Human Immunodeficiency Virus and

AIDS 888

Chapter Summary 898

Problems 899

Chemical Connections

30A Monoclonal Antibodies Wage War on Breast

Cancer 876

30B Antibiotics: A Double-Edged Sword 885

30C A Little Swine Goes a Long Way 894

30D Inflammation 896

Chapter 31 Body Fluids 902

To access this online-only chapter, search for

ISBN 978-1-337-57135-7 at www.cengage.com

and visit this book’s companion website.

Appendix I Exponential Notation A-1

Appendix II Significant Figures A-5

Answers To In-Text And Odd-Numbered

End-Of-Chapter Problems A-8

Glossary G-1

Index I-1

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