Principles of General, Organic and Biological Chemistry

Front Cover......Page 1
Title Page......Page 6
Copyright Page......Page 7
About the Author......Page 9
Contents in Brief......Page 10
Contents......Page 11
Preface......Page 16
Acknowledgments......Page 22
List of How To's......Page 24
List of Applications......Page 25
1 Matter and Measurement......Page 28
1.1 Chemistry—The Science of Everyday Experience......Page 29
1.2 States of Matter......Page 30
1.3 Classification of Matter......Page 32
1.4A: The Metric System......Page 36
1.4C: Measuring Mass......Page 37
1.5 Significant Figures......Page 39
1.5A: Determining the Number of Significant Figures......Page 40
1.5B: Using Significant Figures in Multiplication and Division......Page 41
1.5C: Using Significant Figures in Addition and Subtraction......Page 42
1.6 Scientific Notation......Page 43
1.7A: Conversion Factors......Page 46
1.7B: Solving a Problem Using One Conversion Factor......Page 47
1.7C: Solving a Problem Using Two or More Conversion Factors......Page 48
1.8 FOCUS ON HEALTH & MEDICINE: Problem Solving Using Clinical Conversion Factors......Page 49
1.9 Temperature......Page 51
1.10A: Density......Page 53
1.10B: Specific Gravity......Page 54
KEY CONCEPTS......Page 55
UNDERSTANDING KEY CONCEPTS......Page 56
ADDITIONAL PROBLEMS......Page 57
ANSWERS TO SELECTED PROBLEMS......Page 59
2 Atoms and the Periodic Table......Page 61
2.1 Elements......Page 62
2.1B: FOCUS ON THE HUMAN BODY: The Elements of Life......Page 63
2.1C: Compounds......Page 65
2.2 Structure of the Atom......Page 67
2.3A: Isotopes, Atomic Number, and Mass Number......Page 71
2.3C: FOCUS ON HEALTH & MEDICINE: Isotopes in Medicine......Page 73
2.4 The Periodic Table......Page 74
2.4B: Characteristics of Groups 1A, 2A, 7A, and 8A......Page 75
2.4C: The Unusual Nature of Carbon......Page 78
2.5 Electronic Structure......Page 79
2.6A: First-Row Elements (Period 1)......Page 81
2.6B: Second-Row Elements (Period 2)......Page 82
2.6C: Other Elements......Page 83
2.7A: Relating Valence Electrons to Group Number......Page 84
2.7B: Electron-Dot Symbols......Page 85
2.8A: Atomic Size......Page 86
2.8B: Ionization Energy......Page 87
KEY CONCEPTS......Page 88
UNDERSTANDING KEY CONCEPTS......Page 89
ADDITIONAL PROBLEMS......Page 90
BEYOND THE CLASSROOM......Page 92
ANSWERS TO SELECTED PROBLEMS......Page 93
3 Ionic and Covalent Compounds......Page 95
3.1 Introduction to Bonding......Page 96
3.2A: Cations and Anions......Page 97
3.2B: Relating Group Number to Ionic Charge for Main Group Elements......Page 100
3.2D: FOCUS ON THE HUMAN BODY: Important Ions in the Body......Page 101
3.3 Ionic Compounds......Page 102
3.3A: Formulas for Ionic Compounds......Page 103
3.3B: FOCUS ON HEALTH & MEDICINE: Ionic Compounds in Consumer Products......Page 104
3.4A: Naming Cations......Page 105
3.4C: Naming Ionic Compounds with Cations from Main Group Metals......Page 106
3.4D: Naming Ionic Compounds Containing Metals with Variable Charge......Page 107
3.4E: Writing a Formula from the Name of an Ionic Compound......Page 108
3.5 Physical Properties of Ionic Compounds......Page 109
3.6 Polyatomic Ions......Page 110
3.6B: Naming Ionic Compounds with Polyatomic Ions......Page 111
3.6C: FOCUS ON HEALTH & MEDICINE: Useful Ionic Compounds......Page 112
3.7 Covalent Bonding......Page 113
3.8A: Drawing Lewis Structures......Page 115
3.9 Naming Covalent Compounds......Page 116
3.10 Molecular Shape......Page 117
3.10C: Four Groups Around an Atom......Page 118
3.11 Electronegativity and Bond Polarity......Page 121
3.12 Polarity of Molecules......Page 123
KEY CONCEPTS......Page 125
ADDITIONAL PROBLEMS......Page 126
CHALLENGE PROBLEMS......Page 129
ANSWERS TO SELECTED PROBLEMS......Page 130
4 Energy and Matter......Page 132
4.1 Energy......Page 133
4.1B: FOCUS ON THE HUMAN BODY: Energy and Nutrition......Page 134
4.2 The Three States of Matter......Page 136
4.3 Intermolecular Forces......Page 137
4.3B: Dipole–Dipole Interactions......Page 138
4.3C: Hydrogen Bonding......Page 139
4.4 Boiling Point and Melting Point......Page 141
4.5 Energy and Phase Changes......Page 142
4.5A: Converting a Solid to a Liquid......Page 143
4.5B: Converting a Liquid to a Gas......Page 144
4.5C: Converting a Solid to a Gas......Page 145
4.6 Heating and Cooling Curves......Page 146
KEY CONCEPTS......Page 148
UNDERSTANDING KEY CONCEPTS......Page 149
ADDITIONAL PROBLEMS......Page 150
ANSWERS TO SELECTED PROBLEMS......Page 152
5 Chemical Reactions......Page 154
5.1A: General Features......Page 155
5.1B: Writing Chemical Equations......Page 157
5.2 Balancing Chemical Equations......Page 159
5.3 The Mole and Avogadro's Number......Page 162
5.4A: Molar Mass......Page 165
5.4B: Relating Grams to Moles......Page 166
5.5 Mole Calculations in Chemical Equations......Page 167
5.6A: Converting Moles of Reactant to Grams of Product......Page 169
5.6B: Converting Grams of Reactant to Grams of Product......Page 171
5.7A: General Features of Oxidation–Reduction Reactions......Page 175
5.7B: Examples of Oxidation–Reduction Reactions......Page 177
5.7C: FOCUS ON HEALTH & MEDICINE: Pacemakers......Page 178
5.8A: Heat of Reaction......Page 179
5.8B: Energy Diagrams......Page 180
5.9A: How Concentration and Temperature Affect Reaction Rate......Page 182
5.9B: Catalysts......Page 183
5.10 FOCUS ON THE HUMAN BODY: Body Temperature......Page 184
KEY CONCEPTS......Page 186
UNDERSTANDING KEY CONCEPTS......Page 187
ADDITIONAL PROBLEMS......Page 188
ANSWERS TO SELECTED PROBLEMS......Page 191
6 Gases......Page 194
6.1B: Gas Pressure......Page 195
6.1C: FOCUS ON HEALTH & MEDICINE: Blood Pressure......Page 196
6.2 Boyle's Law Relating Gas Pressure and Volume......Page 197
6.3 Charles's Law Relating Gas Volume and Temperature......Page 200
6.4 Gay–Lussac's Law Relating Gas Pressure and Temperature......Page 202
6.5 The Combined Gas Law......Page 204
6.6 Avogadro's Law Relating Gas Volume and Moles......Page 205
6.7 The Ideal Gas Law......Page 208
6.8 Dalton's Law and Partial Pressures......Page 211
6.9A: The Ozone Layer......Page 213
6.9B: Carbon Dioxide and Global Warming......Page 214
KEY EQUATIONS—THE GAS LAWS......Page 215
UNDERSTANDING KEY CONCEPTS......Page 216
ADDITIONAL PROBLEMS......Page 217
ANSWERS TO SELECTED PROBLEMS......Page 219
7 Solutions......Page 221
7.1 Introduction......Page 222
7.2 Solubility—General Features......Page 224
7.3A: Temperature Effects......Page 227
7.3B: Pressure Effects......Page 228
7.4A: Weight/Volume Percent......Page 229
7.4B: Volume/Volume Percent......Page 230
7.4C: Using a Percent Concentration as a Conversion Factor......Page 231
7.4D: Parts Per Million......Page 232
7.5 Concentration Units—Molarity......Page 233
7.6 Dilution......Page 236
7.7A: Osmotic Pressure......Page 239
7.7B: FOCUS ON THE HUMAN BODY: Osmosis and Biological Membranes......Page 240
7.7C: FOCUS ON HEALTH & MEDICINE: Dialysis......Page 242
KEY EQUATIONS—CONCENTRATION......Page 243
UNDERSTANDING KEY CONCEPTS......Page 244
ADDITIONAL PROBLEMS......Page 245
ANSWERS TO SELECTED PROBLEMS......Page 247
8 Acids and Bases......Page 249
8.1 Introduction to Acids and Bases......Page 250
8.1A: Brønsted–Lowry Acids......Page 251
8.1B: Brønsted–Lowry Bases......Page 253
8.2 The Reaction of a Brønsted–Lowry Acid with a Brønsted–Lowry Base......Page 255
8.3 Acid and Base Strength......Page 257
8.4 Dissociation of Water......Page 261
8.5A: Calculating pH......Page 264
8.5B: Calculating pH Using a Calculator......Page 266
8.5C: FOCUS ON THE HUMAN BODY: The pH of Body Fluids......Page 267
8.6A: Reaction of Acids with Hydroxide Bases......Page 268
8.6B: Reaction of Acids with Bicarbonate and Carbonate......Page 270
8.7 Titration......Page 271
8.8 Buffers......Page 272
8.8A: General Characteristics of a Buffer......Page 273
8.8B: FOCUS ON THE ENVIRONMENT: Acid Rain and a Naturally Buffered Lake......Page 274
8.9 FOCUS ON THE HUMAN BODY: Buffers in the Blood......Page 275
KEY CONCEPTS......Page 277
ADDITIONAL PROBLEMS......Page 278
BEYOND THE CLASSROOM......Page 280
ANSWERS TO SELECTED PROBLEMS......Page 281
9 Nuclear Chemistry......Page 283
9.1A: Isotopes......Page 284
9.1B: Types of Radiation......Page 285
9.2A: Alpha Emission......Page 287
9.2B: Beta Emission......Page 289
9.2C: Positron Emission......Page 290
9.2D: Gamma Emission......Page 291
9.3A: General Features......Page 293
9.3B: Archaeological Dating......Page 294
9.4A: Measuring the Radioactivity in a Sample......Page 295
9.4B: Measuring Human Exposure to Radioactivity......Page 296
9.5A: Radioisotopes Used in Diagnosis......Page 297
9.5B: Radioisotopes Used in Treatment......Page 298
9.5C: Positron Emission Tomography—PET Scans......Page 299
9.6A: Nuclear Fission......Page 300
9.7 FOCUS ON HEALTH & MEDICINE: Medical Imaging Without Radioactivity......Page 302
KEY TERMS......Page 303
UNDERSTANDING KEY CONCEPTS......Page 304
ADDITIONAL PROBLEMS......Page 305
BEYOND THE CLASSROOM......Page 307
ANSWERS TO SELECTED PROBLEMS......Page 308
10 Introduction to Organic Molecules......Page 310
10.1 Introduction to Organic Chemistry......Page 311
10.2 Characteristic Features of Organic Compounds......Page 312
10.3A: Condensed Structures......Page 315
10.3B: Skeletal Structures......Page 317
10.4 Functional Groups......Page 318
10.4B: Compounds Containing a Single Bond to a Heteroatom......Page 319
10.4C: Compounds Containing a C=O Group......Page 321
10.5A: Introduction......Page 324
10.5B: Acyclic Alkanes Having Fewer Than Five Carbons......Page 325
10.5C: Acyclic Alkanes Having Five or More Carbons......Page 327
10.6C: Naming Substituents......Page 329
10.6D: Naming an Acyclic Alkane......Page 330
10.6E: FOCUS ON HEALTH & MEDICINE: Naming New Drugs......Page 333
10.7A: Simple Cycloalkanes......Page 334
10.7B: Naming Cycloalkanes......Page 335
10.8 FOCUS ON THE ENVIRONMENT: Fossil Fuels......Page 336
10.9 Physical Properties......Page 337
10.10 FOCUS ON THE ENVIRONMENT: Combustion......Page 338
KEY TERMS......Page 339
UNDERSTANDING KEY CONCEPTS......Page 340
ADDITIONAL PROBLEMS......Page 341
BEYOND THE CLASSROOM......Page 345
ANSWERS TO SELECTED PROBLEMS......Page 346
11 Unsaturated Hydrocarbons......Page 349
11.1 Alkenes and Alkynes......Page 350
11.2 Nomenclature of Alkenes and Alkynes......Page 352
11.3A: Stereoisomers—A New Class of Isomer......Page 354
11.3B: FOCUS ON HEALTH & MEDICINE: Saturated and Unsaturated Fatty Acids......Page 356
11.4 FOCUS ON HEALTH & MEDICINE: Oral Contraceptives......Page 358
11.5A: Addition of Hydrogen—Hydrogenation......Page 359
11.5B: Addition of Water—Hydration......Page 360
11.6 FOCUS ON HEALTH & MEDICINE: Margarine or Butter?......Page 361
11.7A: Synthetic Polymers......Page 363
11.7B: FOCUS ON THE ENVIRONMENT: Polymer Recycling......Page 366
11.9A: Monosubstituted Benzenes......Page 367
11.9C: Polysubstituted Benzenes......Page 368
11.10B: Phenols as Antioxidants......Page 370
KEY CONCEPTS......Page 371
UNDERSTANDING KEY CONCEPTS......Page 372
ADDITIONAL PROBLEMS......Page 373
BEYOND THE CLASSROOM......Page 376
ANSWERS TO SELECTED PROBLEMS......Page 377
12 Organic Compounds That Contain Oxygen or Sulfur......Page 380
12.1 Introduction......Page 381
12.2 Structure and Properties of Alcohols......Page 382
12.2A: Physical Properties of Alcohols......Page 383
12.2B: Nomenclature of Alcohols......Page 384
12.3 Structure and Properties of Ethers......Page 385
12.4B: FOCUS ON HEALTH & MEDICINE: Ethers as Anesthetics......Page 387
12.5A: Dehydration......Page 388
12.5B: Oxidation......Page 389
12.5C: FOCUS ON THE HUMAN BODY: Oxidation and Blood Alcohol Screening......Page 391
12.5D: FOCUS ON HEALTH & MEDICINE: The Metabolism of Ethanol......Page 392
12.6 Thiols......Page 393
12.7A: Naming Aldehydes......Page 394
12.7B: Naming Ketones......Page 395
12.7C: Physical Properties......Page 396
12.8 FOCUS ON HEALTH & MEDICINE: Interesting Aldehydes and Ketones......Page 397
12.9 Oxidation of Aldehydes......Page 398
12.10A: What It Means to Be Chiral or Achiral......Page 400
12.10B: Locating Chirality Centers......Page 401
12.10C: Fischer Projections......Page 403
12.11 FOCUS ON HEALTH & MEDICINE: Chiral Drugs......Page 405
KEY TERMS......Page 407
KEY CONCEPTS......Page 408
UNDERSTANDING KEY CONCEPTS......Page 409
ADDITIONAL PROBLEMS......Page 410
BEYOND THE CLASSROOM......Page 414
ANSWERS TO SELECTED PROBLEMS......Page 415
13 Carboxylic Acids, Esters, Amines, and Amides......Page 418
13.1 Introduction......Page 419
13.2A: Naming a Carboxylic Acid—RCOOH......Page 420
13.2B: Naming an Ester—RCOOR'......Page 421
13.3 Physical Properties of Carboxylic Acids and Esters......Page 422
13.4A: FOCUS ON HEALTH & MEDICINE: Skin Care Products......Page 423
13.4B: FOCUS ON HEALTH & MEDICINE: Aspirin and Anti-Inflammatory Agents......Page 424
13.5A: Reaction with Bases......Page 425
13.5B: How Does Soap Clean Away Dirt?......Page 426
13.6A: Ester Formation......Page 428
13.6B: Ester Hydrolysis......Page 429
13.6C: FOCUS ON HEALTH & MEDICINE: Olestra, a Synthetic Fat......Page 430
13.7A: Structure and Classification......Page 431
13.7B: Nomenclature......Page 433
13.7C: Physical Properties......Page 434
13.8A: Reaction of Amines with Acids......Page 436
13.8B: Ammonium Salts......Page 437
13.8C: FOCUS ON HEALTH & MEDICINE: Ammonium Salts as Useful Drugs......Page 438
13.9 Amides......Page 439
13.9A: Naming an Amide......Page 440
13.9C: Amide Hydrolysis......Page 441
13.10 Interesting Amines and Amides......Page 442
13.10A: FOCUS ON THE HUMAN BODY: Epinephrine and Related Compounds......Page 443
13.10B: FOCUS ON HEALTH & MEDICINE: Penicillin......Page 444
KEY CONCEPTS......Page 445
UNDERSTANDING KEY CONCEPTS......Page 446
ADDITIONAL PROBLEMS......Page 447
CHALLENGE PROBLEMS......Page 449
ANSWERS TO SELECTED PROBLEMS......Page 450
14 Carbohydrates......Page 454
14.1 Introduction......Page 455
14.2 Monosaccharides......Page 456
14.2A: Fischer Projection Formulas......Page 458
14.2B: Monosaccharides with More Than One Chirality Center......Page 459
14.2C: Common Monosaccharides......Page 461
14.3 The Cyclic Forms of Monosaccharides......Page 462
14.3A: Haworth Projections......Page 463
14.3B: The Cyclic Forms of Fructose, a Ketohexose......Page 464
14.4A: Reduction of the Aldehyde Carbonyl Group......Page 465
14.4B: Oxidation of the Aldehyde Carbonyl Group......Page 466
14.5 Disaccharides......Page 468
14.5A: FOCUS ON HEALTH & MEDICINE: Lactose Intolerance......Page 470
14.5B: FOCUS ON HEALTH & MEDICINE: Sucrose and Artificial Sweeteners......Page 471
14.6A: Cellulose......Page 472
14.6B: Starch......Page 473
14.7 FOCUS ON THE HUMAN BODY: Blood Type......Page 475
KEY REACTIONS......Page 477
UNDERSTANDING KEY CONCEPTS......Page 478
ADDITIONAL PROBLEMS......Page 479
CHALLENGE PROBLEMS......Page 481
ANSWERS TO SELECTED PROBLEMS......Page 482
15 Lipids......Page 486
15.1 Introduction to Lipids......Page 487
15.2 Fatty Acids......Page 488
15.3 Waxes......Page 490
15.4A: General Features......Page 492
15.4B: FOCUS ON HEALTH & MEDICINE: Fats and Oils in the Diet......Page 494
15.5 Hydrolysis of Triacylglycerols......Page 496
15.5A: FOCUS ON THE HUMAN BODY: Metabolism of Triacylglycerols......Page 497
15.5B: Soap Synthesis......Page 498
15.6 Phospholipids......Page 499
15.7A: Structure of the Cell Membrane......Page 501
15.7B: Transport Across a Cell Membrane......Page 502
15.8 FOCUS ON HEALTH & MEDICINE: Cholesterol, the Most Prominent Steroid......Page 503
15.9 Steroid Hormones......Page 506
15.10 FOCUS ON HEALTH & MEDICINE: Fat-Soluble Vitamins......Page 508
KEY REACTIONS......Page 510
UNDERSTANDING KEY CONCEPTS......Page 511
ADDITIONAL PROBLEMS......Page 512
CHALLENGE PROBLEMS......Page 514
ANSWERS TO SELECTED PROBLEMS......Page 515
16 Amino Acids, Proteins, and Enzymes......Page 519
16.1 Introduction......Page 520
16.2A: General Features of Amino Acids......Page 521
16.2B: Stereochemistry of Amino Acids......Page 522
16.3 Acid–Base Behavior of Amino Acids......Page 524
16.4 Peptides......Page 526
16.5A: Neuropeptides—Enkephalins and Pain Relief......Page 529
16.5B: Peptide Hormones—Oxytocin and Vasopressin......Page 530
16.6A: Primary Structure......Page 531
16.6B: Secondary Structure......Page 532
16.6C: Tertiary and Quaternary Structure......Page 533
16.7A: α-Keratins......Page 535
16.7B: Collagen......Page 536
16.7C: Hemoglobin and Myoglobin......Page 537
16.8A: Protein Hydrolysis......Page 538
16.8B: Protein Denaturation......Page 540
16.9A: Characteristics of Enzymes......Page 541
16.9B: How Enzymes Work......Page 542
16.9C: Enzyme Inhibitors......Page 544
16.10A: Enzyme Levels as Diagnostic Tools......Page 545
16.10B: Treating Disease with Drugs That Interact with Enzymes......Page 546
KEY CONCEPTS......Page 547
UNDERSTANDING KEY CONCEPTS......Page 548
ADDITIONAL PROBLEMS......Page 549
ANSWERS TO SELECTED PROBLEMS......Page 551
17 Nucleic Acids and Protein Synthesis......Page 554
17.1A: Nucleosides—Joining a Monosaccharide and a Base......Page 555
17.2 Nucleic Acids......Page 560
17.3 The DNA Double Helix......Page 562
17.4 Replication......Page 565
17.5 RNA......Page 567
17.7 The Genetic Code......Page 569
17.1B: Nucleotides—Joining a Nucleoside with a Phosphate......Page 558
[1] Initiation......Page 571
[3] Termination......Page 572
17.9 Mutations and Genetic Diseases......Page 574
17.11 FOCUS ON HEALTH & MEDICINE: Viruses......Page 576
KEY CONCEPTS......Page 579
UNDERSTANDING KEY CONCEPTS......Page 580
ADDITIONAL PROBLEMS......Page 581
ANSWERS TO SELECTED PROBLEMS......Page 584
18 Energy and Metabolism......Page 587
18.1A: Energy Production in the Cell......Page 588
18.1B: The Four Stages of Catabolism......Page 590
18.2 ATP and Energy Production......Page 591
18.3A: Coenzymes NAD[sup(+)] and NADH......Page 593
18.3C: Coenzyme A......Page 595
18.4A: The Steps in Glycolysis......Page 596
18.5 The Fate of Pyruvate......Page 600
18.5B: FOCUS ON HEALTH & MEDICINE: Conversion to Lactate......Page 601
18.5C: Conversion to Ethanol......Page 602
18.6B: Specific Steps of the Citric Acid Cycle......Page 603
18.7A: The Electron Transport Chain......Page 606
18.7C: ATP Yield from Oxidative Phosphorylation......Page 608
18.8 The ATP Yield from Glucose......Page 609
18.9A: Fatty Acid Catabolism by β-Oxidation......Page 611
18.10 Ketone Bodies......Page 614
18.11A: Degradation of Amino Acids—The Fate of the Amino Group......Page 615
18.11B: Degradation of Amino Acids—The Fate of the Carbon Skeleton......Page 617
KEY CONCEPTS......Page 618
UNDERSTANDING KEY CONCEPTS......Page 619
ADDITIONAL PROBLEMS......Page 620
ANSWERS TO SELECTED PROBLEMS......Page 622
Appendix: Useful Mathematical Concepts......Page 624
Glossary......Page 630
Credits......Page 638
Index......Page 640