General, Organic, and Biological Chemistry

Kenneth W. Raymond is the author of General Organic and Biological Chemistry: An Integrated Approach, 4th Edition, published by Wiley.

chapter 1 Science and Measurements 1

1.1 The Scientific Method 2

HealthLink Science and Medicine5

1.2 Matter and Energy 5

1.3 Units of Measurement 9

1.4 Scientific Notation, SI and Metric Prefixes 13

1.5 Measurements and Significant Figures 15

HealthLink Body Mass Index 18

HealthLink Body Temperature 21

1.6 Conversion Factors and the Factor Label Method 22

1.7 Density, Specific Gravity, and Specific Heat 25

HealthLink Making Weight 28

1.8 Measurements in General Chemistry,Organic Chemistry, and Biochemistry 29

chapter 2 A toms and Elements 42

2.1 Atoms 44

2.2 Elements 46

2.3 Trace Elements 48

2.4 Atomic Number and Mass Number 51

HealthLink Stable Isotopes and Drug Testing 53

2.5 Periodic Table 54

HealthLink Lead 58

2.6 The Mole 59

2.7 The Arrangement of Electrons 62

BiochemistryLink Bioluminescence 67

2.8 Radioactive Isotopes 68

2.9 Radioisotopes in Medicine 71

HealthLink Radioisotopes for Sale 79

HealthLink CT and MRI Imaging 79

chapter 3 Compounds 88

3.1 Ions 90

3.2 The Octet Rule 93

BiochemistryLink Ionophores and Biological Ion Transport 95

3.3 Ionic Compounds 96

HealthLink Pass the Salt, Please 100

3.4 Covalent Bonds 101

3.5 Molecules 103

HealthLink Dental Fillings 105

3.6 Formula Weight, Molecular Weight,and Molar Mass 105

HealthLink Nitric Oxide 108

chapter 4 An Introduct ion to Organic Compounds 116

4.1 Structural Formulas 118

4.2 Polar Covalent Bonds, Shape, and Polarity 123

HealthLink Prion Diseases 128

4.3 Noncovalent Interactions 130

4.4 Families of Organic Compounds 132

BiochemistryLink Ethylene, a Plant Hormone 134

HealthLink Sunscreens 139

chapter 5 Reactions 150

5.1 Chemical Equations 152

5.2 Reaction Types 156

5.3 Reactions Involving Water 158

5.4 Oxidation and Reduction 161

HealthLink Antiseptics and Oxidation 166

5.5 Mole and Mass Relationships in Reactions 167

5.6 Calculating the Yield of a Reaction 171

5.7 Free Energy and Reaction Rate 174

HealthLink Carbonic Anhydrase 177

chapter 6 Gases, Solutions,Colloids, and Suspensions 190

6.1 Gases and Pressure 192

HealthLink Blood Pressure 196

6.2 The Gas Laws 197

6.3 Partial Pressure 202

HealthLink Breathing 203

6.4 Solutions 204

6.5 Precipitation Reactions 207

6.6 Solubility of Gases in Water 209

6.7 Organic and Biochemical Compounds 212

HealthLink Prodrugs 215

6.8 Concentration 216

6.9 Dilution 221

6.10 Colloids and Suspensions 222

HealthLink Saliva 224

6.11 Diffusion and Osmosis 225

HealthLink Diffusion and the Kidneys 227

chapter 7 Acids, Bases, and Equilibrium 238

7.1 Acids and Bases 240

7.2 Brønsted–Lowry Acids and Bases 241

7.3 Equilibrium 243

7.4 Le Châtelier’s Principle 246

BiochemistryLink Diving Mammals, Oxygen, and Myoglobin 249

7.5 Ionization of Water 250

7.6 The pH Scale 251

7.7 Acid and Base Strength 254

BiochemistryLink Plants as pH Indicators 257

7.8 Neutralizing Acids and Bases 257

7.9 Effect of pH on Acid and Conjugate Base Concentrations 259

7.10 Buffers 261

BiochemistryLink The Henderson–Hasselbalch Equation 262

7.11 Maintaining the pH of Blood Serum 263

chapter 8 Organic Reactions 1—Hydrocarbons,Carboxylic Acids,Amines, and Related Compounds 276

8.1 Alkanes 278

8.2 Constitutional Isomers 282

8.3 Conformations 284

8.4 Cycloalkanes 285

8.5 Alkenes, Alkynes, and Aromatic Compounds 287

8.6 Reactions of Hydrocarbons 291

8.7 Carboxylic Acids 297

8.8 Phenols 299

HealthLink A Chili Pepper Painkiller 300

8.9 Carboxylic Acids and Phenols as Weak Organic Acids 301

8.10 Preparing Esters 304

HealthLink Alpha Hydroxy Acids 306

8.11 Amines 307

HealthLink Adrenaline and Related Compounds 310

8.12 Amines as Weak Organic Bases 311

8.13 Amides 313

HealthLink Biofilms 315

BiochemistryLink A Cure for Fleas 316

chapter 9 Organic Reactions 2—Alcohols, Ethers, Aldehydes, and Ketones 334

9.1 Alcohols, Ethers, and Related Compounds 336

9.2 Preparation 339

9.3 Reactions 341

9.4 Aldehydes and Ketones 344

9.5 Oxidation of Aldehydes 347

HealthLink Aldehyde Dehydrogenase 349

9.6 Reduction of Aldehydes and Ketones 349

HealthLink Protective Enzymes 351

9.7 Reactions of Alcohols with Aldehydes and Ketones 352

HealthLink Drugs in the Environment 354

chapter 10 Carbohydrates 370

10.1 Monosaccharides 372

10.2 Stereoisomers 374

10.3 Important Monosaccharides and Monosaccharide Derivatives 381

10.4 Reactions of Monosaccharides 384

10.5 Monosaccharides in Their Cyclic Form 386

10.6 Oligosaccharides 390

HealthLink Natural and Artificial Sweeteners 397

HealthLink Stevia 400

10.7 Polysaccharides 401

chapter 11 Lipids and Membranes 420

11.1 Fatty Acids 422

HealthLink Omega-3 Fatty Acids 426

11.2 Waxes 427

11.3 Triglycerides 429

HealthLink Trans Fats 435

HealthLink Olestra 436

11.4 Phospholipids and Glycolipids 437

11.5 Steroids 441

HealthLink Anabolic Steroids 445

11.6 Eicosanoids 445

11.7 Membranes 447

chapter 12 Peptides, Proteins, and Enzymes 458

12.1 Amino Acids 460

12.2 The Peptide Bond 464

12.3 Peptides, Proteins, and pH 468

12.4 Protein Structure 469

BiochemistryLink Hemoglobin, a Globular Protein, and Collagen, a Fibrous Protein 475

HealthLink Immunotherapy 476

12.5 Denaturation 477

12.6 Enzymes 478

12.7 Control of Enzyme-Catalyzed Reactions 482

HealthLink Tamiflu and Relenza as Enzyme Inhibitors 486

HealthLink Proteins in Medicine 489

chapter 13 Nucleic Acids 498

13.1 Nucleic Acid Building Blocks 500

13.2 Nucleoside Di- and Triphosphates, Cyclic Nucleotides 505

13.3 Polynucleotides 506

13.4 DNA Structure 509

13.5 Denaturation 512

13.6 Nucleic Acids and Information Flow 514

13.7 DNA Replication 515

13.8 Transcription and RNA 517

HealthLink Lupus 519

13.9 Translation 520

13.10 Control of Gene Expression 522

HealthLink RNA Interference 524

13.11 Mutation 524

13.12 Recombinant DNA 525

BiochemistryLink Glowing Cats 528

13.13 DNA Fingerprinting 529

chapter 14 Metabolism 540

14.1 Metabolic Pathways, Energy, and Coupled Reactions 542

14.2 Overview of Metabolism 543

14.3 Digestion 548

14.4 Glycolysis 551

14.5 Gluconeogenesis 556

14.6 Glycogen Metabolism 558

14.7 Citric Acid Cycle 560

14.8 Electron Transport Chain and Oxidative Phosphorylation 562

HealthLink Brown Fat 566

14.9 Lipid Metabolism 566

14.10 Amino Acid Metabolism 571

Appendix A Important Families of Organic Compounds 582

Appendix B Naming Ions, Ionic Compounds, Binary Molecules, and Organic Compounds 584

Appendix C Answers to Odd-Numbered

Problems 591

Appendix D Glossary 639

Index I-1