Introduction to General, Organic, and Biochemistry

1 An Introduction to Chemistry 1 1.1 Why Study Chemistry? 2 1.2 The Nature of Chemistry 2 1.3 Thinking Like a Chemist 2 1.4 A Scientific Approach to Problem Solving 3 Molecular Gastronomy 4 1.5 The Scientific Method 4 1.6 The Particulate Nature of Matter 5 1.7 Physical States of Matter 6 1.8 Classifying Matter 8 Review 10 Review Questions 11 Paired Exercises, Additional Exercises 12 2 Standards for Measurement 13 2.1 Scientific Notation 14 2.2 Measurement and Uncertainty 15 2.3 Significant Figures 17 2.4 Significant Figures in Calculations 18 2.5 The Metric System 21 2.6 Dimensional Analysis 23 Keeping Track of Units 27 2.7 Measuring Mass and Volume 27 Setting Standards 29 2.8 Measurement of Temperature 31 Taking the Temperature of Old Faithful 33 2.9 Density 34 Review 37 Review Questions 39 Paired Exercises, Additional Exercises Challenge Exercises 39 Answers to Practice Exercises 42 3 Elements and Compounds 43 3.1 Elements 44 3.2 Distribution of Elements 44 3.3 Names of the Elements 46 3.4 Symbols of the Elements 46 3.5 Introduction to the Periodic Table 48 Elements on UTube? 48 3.6 Elements in Their Natural States 50 3.7 Elements That Exist as Diatomic Molecules 50 Using Oxygen to Revive Damaged Art 51 3.8 Compounds 52 3.9 Chemical Formulas 53 Cars: Is Hydrogen the Answer? 54 Review 56 Review Questions 58 Paired Exercises, Additional Exercises Challenge Exercises 58 Answers to Practice Exercises 60 4 Properties of Matter 61 4.1 Properties of Substances 62 Making Money 63 4.2 Physical Changes 64 4.3 Chemical Changes 64 4.4 Conservation of Mass 66 4.5 Learning to Solve Problems 67 4.6 Energy 67 4.7 Heat: Quantitative Measurement 68 Popping Popcorn 70 4.8 Energy in Chemical Changes 71 4.9 Conservation of Energy 71 4.10 Energy in the Real World 72 Review 73 Review Questions 74 Paired Exercises, Additional Exercises Challenge Exercises 74 Answers to Practice Exercises 77 Review for Chapters 1--4 78 5 Early Atomic Theory and Structure 81 5.1 Early Thoughts 82 5.2 Dalton's Model of the Atom 82 5.3 Composition of Compounds 83 5.4 The Nature of Electric Charge 84 5.5 Discovery of Ions 84 5.6 Subatomic Parts of the Atom 85 5.7 The Nuclear Atom 87 5.8 Isotopes of the Elements 89 Isotope Detectives 91 5.9 Atomic Mass 91 Review 94 Review Questions 95 Paired Exercises, Additional Exercises Challenge Exercises 95 Answers to Practice Exercises 97 6 Nomenclature of Inorganic Compounds 98 6.1 Common and Systematic Names 99 6.2 Elements and Ions 99 What's in a Name? 101 6.3 Writing Formulas from Names of Ionic Compounds 103 6.4 Naming Binary Compounds 105 6.5 Naming Compounds Containing Polyatomic Ions 111 6.6 Acids 112 Review 114 Review Questions 115 Paired Exercises, Additional Exercises Challenge Exercises 115 Answers to Practice Exercises 118 Review for Chapters 5--6 119 7 Quantitative Composition of Compounds 121 7.1 The Mole 122 7.2 Molar Mass of Compounds 126 7.3 Percent Composition of Compounds 129 7.4 Empirical Formula versus Molecular Formula 132 Vanishing Coins? 133 7.5 Calculating Empirical Formulas 134 7.6 Calculating the Molecular Formula from the Empirical Formula 137 Review 138 Review Questions 139 Paired Exercises, Additional Exercises Challenge Exercises 139 Answers to Practice Exercises 142 8 Chemical Equations 143 8.1 The Chemical Equation 144 8.2 Writing and Balancing Chemical Equations 145 8.3 Information in a Chemical Equation 150 8.4 Types of Chemical Equations 151 CO Poisoning--A Silent Killer 152 8.5 Heat in Chemical Reactions 157 8.6 Global Warming: The Greenhouse Effect 160 Decreasing Carbon Footprints 161 Review 163 Review Questions 164 Paired Exercises, Additional Exercises Challenge Exercises 164 Answers to Practice Exercises 167 9 Calculations from Chemical Equations 168 9.1 A Short Review 169 9.2 Introduction to Stoichiometry 169 9.3 Mole--Mole Calculations 171 9.4 Mole--Mass Calculations 174 9.5 Mass--Mass Calculations 176 Trans-forming Fats 230 Goal! A Spherical Molecule 231 11.7 Lewis Structures of Compounds 231 11.8 Complex Lewis Structures 235 11.9 Compounds Containing Polyatomic Ions 236 11.10 Molecular Shape 237 Strong Enough to Stop a Bullet? 238 11.11 The Valence Shell Electron Pair Repulsion (VSEPR) Model 238 Review 242 Review Questions 244 Paired Exercises, Additional Exercises Challenge Exercises 244 Answers to Practice Exercises 247 Review for Chapters 10--11 248 12 The Gaseous State of Matter 251 12.1 General Properties 252 12.2 The Kinetic-Molecular Theory 252 12.3 Measurement of Pressure of Gases 254 12.4 Dependence of Pressure on Number of Molecules and Temperature 255 12.5 Boyle's Law 257 12.6 Charles' Law 260 12.7 Gay-Lussac's Law 263 12.8 Combined Gas Laws 264 12.9 Dalton's Law of Partial Pressures 267 Messenger Molecules 268 12.10 Avogadro's Law 269 12.11 Mole--Mass--Volume Relationships of Gases 270 12.12 Density of Gases 272 12.13 Ideal Gas Law 273 12.14 Gas Stoichiometry 275 12.15 Real Gases 279 Wetland Blanket for Global Warming 281 9.6 Limiting-Reactant and Yield Calculations 177 A Shrinking Technology 178 Review 184 Review Questions 185 Paired Exercises, Additional Exercises Challenge Exercises 186 Answers to Practice Exercises 190 Review for Chapters 7--9 191 10 Modern Atomic Theory and the Periodic Table 194 10.1 A Brief History 195 10.2 Electromagnetic Radiation 195 You Light Up My Life 196 10.3 The Bohr Atom 196 10.4 Energy Levels of Electrons 198 Atomic Clocks 200 10.5 Atomic Structures of the First 18 Elements 200 10.6 Electron Structures and the Periodic Table 203 Collecting the Elements 204 Review 208 Review Questions 209 Paired Exercises, Additional Exercises Challenge Exercises 210 Answers to Practice Exercises 212 11 Chemical Bonds: The Formation of Compounds from Atoms 213 11.1 Periodic Trends in Atomic Properties 214 11.2 Lewis Structures of Atoms 217 11.3 The Ionic Bond: Transfer of Electrons from One Atom to Another 218 11.4 Predicting Formulas of Ionic Compounds 224 11.5 The Covalent Bond: Sharing Electrons 226 11.6 Electronegativity 227 Review 282 Review Questions 285 Paired Exercises, Additional Exercises Challenge Exercises 286 Answers to Practice Exercises 289 13 Properties of Liquids 290 13.1 What Is a Liquid? 291 13.2 Evaporation 291 13.3 Vapor Pressure 292 13.4 Surface Tension 293 13.5 Boiling Point 294 Chemical Eye Candy 296 13.6 Freezing Point or Melting Point 296 13.7 Changes of State 297 13.8 The Hydrogen Bond 298 How Sweet It Is! 300 13.9 Hydrates 301 13.10 Water, a Unique Liquid 303 13.11 Water Purification 307 Quenching the Thirst for Clean Water 309 Review 310 Review Questions 311 Paired Exercises, Additional Exercises Challenge Exercises 313 Answers to Practice Exercises 315 14 Solutions 316 14.1 General Properties of Solutions 317 Exploding Silicon 318 14.2 Solubility 318 14.3 Factors Related to Solubility 319 14.4 Rate of Dissolving Solids 323 14.5 Solutions: A Reaction Medium 324 14.6 Concentration of Solutions 325 14.7 Colligative Properties of Solutions 333 The Scoop on Ice Cream 337 14.8 Osmosis and Osmotic Pressure 338 Review 340 Review Questions 341 Paired Exercises, Additional Exercises Challenge Exercises 343 Answers to Practice Exercises 346 Review for Chapters 12--14 347 15 Acids, Bases, and Salts 351 15.1 Acids and Bases 352 15.2 Reactions of Acids 355 15.3 Reactions of Bases 356 15.4 Salts 356 A Cool Fizz 357 15.5 Electrolytes and Nonelectrolytes 357 15.6 Dissociation and Ionization of Electrolytes 358 15.7 Strong and Weak Electrolytes 360 15.8 Ionization of Water 362 15.9 Introduction to pH 363 In the Pink--A Sign of Corrosion 365 15.10 Neutralization 366 15.11 Writing Net Ionic Equations 368 15.12 Acid Rain 371 15.13 Colloids 372 Foam Cars--Wave of the Future? 373 15.14 Properties of Colloids 374 15.15 Applications of Colloidal Properties 374 Review 375 Review Questions 377 Paired Exercises, Additional Exercises Challenge Exercises 377 Answers to Practice Exercises 380 16 Chemical Equilibrium 381 16.1 Reversible Reactions 382 16.2 Rates of Reaction 382 16.3 Chemical Equilibrium 384 16.4 Le Cha telier's Principle 384 New Ways in Fighting Cavities and Avoiding the Drill 385 16.5 Effect of Concentration on Equilibrium 386 16.6 Effect of Volume on Equilibrium 388 16.7 Effect of Temperature on Equilibrium 390 16.8 Effect of Catalysts on Equilibrium 391 16.9 Equilibrium Constants 391 16.10 Ion Product Constant for Water 393 16.11 Ionization Constants 395 16.12 Solubility Product Constant 398 16.13 Acid--Base Properties of Salts 401 16.14 Buffer Solutions: The Control of pH 401 Exchange of Oxygen and Carbon Dioxide in the Blood 402 Review 404 Review Questions 405 Paired Exercises, Additional Exercises Challenge Exercises 406 Answers to Practice Exercises 410 17 Oxidation-Reduction 411 17.1 Oxidation Number 412 17.2 Oxidation--Reduction 415 17.3 Balancing Oxidation--Reduction Equations 416 17.4 Balancing Ionic Redox Equations 419 Sensitive Sunglasses 421 17.5 Activity Series of Metals 423 17.6 Electrolytic and Voltaic Cells 425 Superbattery Uses Hungry Iron Ions 430 Review 431 Review Questions 433 Paired Exercises, Additional Exercises Challenge Exercises 434 Answers to Practice Exercises 436 Review for Chapters 15--17 437 18 Nuclear Chemistry 441 18.1 Discovery of Radioactivity 442 18.2 Natural Radioactivity 443 18.3 Alpha Particles, Beta Particles, and Gamma Rays 445 18.4 Radioactive Disintegration Series 448 18.5 Transmutation of Elements 449 18.6 Artificial Radioactivity 450 18.7 Measurement of Radioactivity 450 18.8 Nuclear Fission 451 Does Your Food Glow in the Dark? 452 18.9 Nuclear Power 453 18.10 The Atomic Bomb 455 18.11 Nuclear Fusion 456 18.12 Mass-Energy Relationship in Nuclear Reactions 457 18.13 Transuranium Elements 458 18.14 Biological Effects of Radiation 458 A Window into Living Organisms 459 Review 460 Review Questions 462 Paired Exercises, Additional Exercises Challenge Exercises 463 Answers to Practice Exercises 465 Review for Chapter 18 465 19 Organic Chemistry: Saturated Hydrocarbons 466 19.1 Organic Chemistry: History and Scope 467 19.2 The Carbon Atom: Bonding and Shape 468 19.3 Organic Formulas and Molecular Models 469 19.4 Classifying Organic Compounds 471 19.5 Hydrocarbons 472 19.6 Saturated Hydrocarbons: Alkanes 473 19.7 Carbon Bonding in Alkanes 474 19.8 Isomerism 475 19.9 Naming Organic Compounds 478 19.10 Introduction to the Reactions of Carbon 484 19.11 Reactions of Alkanes 485 Health, Anesthesia, and Alkyl Halides 488 19.12 Sources of Alkanes 491 19.13 Gasoline: A Major Petroleum Product 491 Gasoline, a Renewable Fuel? 493 19.14 Cycloalkanes 494 Review 497 Review Questions 499 Paired Exercises, Additional Exercises Challenge Exercise 499 Answers to Practice Exercises 503 20 Unsaturated Hydrocarbons 505 20.1 Bonding in Unsaturated Hydrocarbons 506 20.2 Nomenclature of Alkenes 509 20.3 Geometric Isomerism in Alkenes 511 20.4 Cycloalkenes 517 20.5 Preparation and Physical Properties of Alkenes 518 20.6 Chemical Properties of Alkenes 520 20.7 Alkynes: Nomenclature and Preparation 525 20.8 Physical and Chemical Properties of Alkynes 526 20.9 Aromatic Hydrocarbons: Structure 528 20.10 Naming Aromatic Compounds 530 Health and Sunscreens 532 20.11 Polycyclic Aromatic Compounds 535 Graphene--Another Amazing Form of Carbon 536 20.12 Sources and Physical Properties of Aromatic Hydrocarbons 536 20.13 Chemical Properties of Aromatic Hydrocarbons 537 Review 539 Review Questions 541 Paired Exercises, Additional Exercises Challenge Exercises 541 Answers to Practice Exercises 545 21 Polymers: Macromolecules 547 21.1 Macromolecules 548 21.2 Synthetic Polymers 548 21.3 Polymer Types 549 21.4 Addition Polymerization 550 Health and Plasticizers 552 21.5 Addition Polymers: Use and Reuse (Recycling) 553 21.6 Butadiene Polymers 554 Timed-Release Degradation--A Plastic That Self-Destructs 555 21.7 Geometric Isomerism in Polymers 557 Review 558 Review Questions 559 Paired Exercises, Additional Exercises Challenge Exercise 559 Answers to Practice Exercises 560 Review for Chapters 19--21 561 22 Alcohols, Ethers, Phenols, and Thiols 565 22.1 Functional Groups 566 22.2 Classification of Alcohols 566 22.3 Naming Alcohols 568 22.4 Physical Properties of Alcohols 570 22.5 Chemical Properties of Alcohols 572 Menthol--A Cool Chemical 576 22.6 Common Alcohols 580 22.7 Phenols 584 Health and Polyphenols 586 22.8 Properties of Phenols 586 22.9 Production of Phenol 587 22.10 Ethers 588 22.11 Structures and Properties of Ethers 590 22.12 Preparation of Ethers 591 22.13 Thiols 592 Review 593 Review Questions 595 Paired Exercises, Additional Exercises Challenge Exercise 595 Answers to Practice Exercises 600 23 Aldehydes and Ketones 602 23.1 Structures of Aldehydes and Ketones 603 23.2 Naming Aldehydes and Ketones 603 23.3 Bonding and Physical Properties 607 Health, Muscle Rubs, and Camphor 608 23.4 Chemical Properties of Aldehydes and Ketones 610 Microbial Chemical Warfare and Antibiotic Resistance 618 23.5 Common Aldehydes and Ketones 619 23.6 Condensation Polymers 621 Review 622 Review Questions 623 Paired Exercises, Additional Exercises Challenge Exercise 624 Answers to Practice Exercise 628 Review for Chapters 22--23 629 24 Carboxylic Acids and Esters 634 24.1 Carboxylic Acids 635 24.2 Nomenclature and Sources of Aliphatic Carboxylic Acids 635 24.3 Physical Properties of Carboxylic Acids 638 24.4 Classification of Carboxylic Acids 639 Health and MSG 643 24.5 Preparation of Carboxylic Acids 644 24.6 Chemical Properties of Carboxylic Acids 646 24.7 Nomenclature of Esters 648 A "Truly Green" Plastic 651 24.8 Occurrence and Physical Properties of Esters 652 24.9 Polyesters: Condensation Polymers 652 24.10 Chemical Properties of Esters 653 24.11 Glycerol Esters 654 24.12 Soaps and Synthetic Detergents 657 24.13 Esters and Anhydrides of Phosphoric Acid 660 Review 662 Review Questions 664 Paired Exercises, Additional Exercises Challenge Exercises 664 Answers to Practice Exercises 669 25 Amides and Amines: Organic Nitrogen Compounds 670 25.1 Amides: Nomenclature and Physical Properties 671 25.2 Chemical Properties of Amides 674 25.3 Polyamides: Condensation Polymers 675 25.4 Urea 676 25.5 Amines: Nomenclature and Physical Properties 677 25.6 Preparation of Amines 681 25.7 Chemical Properties of Amines 682 Supersolvents 684 25.8 Sources and Uses of Selected Amines 685 Health, Caffeine, and Learning 687 Review 688 Review Questions 690 Paired Exercises, Additional Exercises Challenge Exercise 690 Answers to Practice Exercises 694 Review for Chapters 24--25 695 26 Stereoisomerism 700 26.1 Review of Isomerism 701 26.2 Plane-Polarized Light 701 26.3 Optical Activity 703 26.4 Fischer Projection Formulas 704 26.5 Enantiomers 706 What a Difference a Shape Makes 711 26.6 Racemic Mixtures 711 26.7 Diastereomers and Meso Compounds 713 Health and the Chiral Switch 714 Review 717 Review Questions 718 Paired Exercises, Additional Exercises Challenge Exercise 718 Answers to Practice Exercises 723 27 Carbohydrates 724 27.1 Carbohydrates: A First Class of Biochemicals 725 27.2 Classification of Carbohydrates 726 27.3 Importance of Carbohydrates for Life 728 27.4 Monosaccharides 729 Health and the "Sugar High" 730 27.5 Structure of Glucose and Other Aldoses 731 27.6 Cyclic Structure of Glucose; Mutarotation 734 27.7 Hemiacetals and Acetals 737 27.8 Structures of Galactose and Fructose 738 27.9 Pentoses 739 27.10 Disaccharides 741 27.11 Structures and Properties of Disaccharides 741 27.12 Sweeteners and Diet 744 27.13 Redox Reactions of Monosaccharides 746 27.14 Polysaccharides Derived from Glucose 750 Screening for Cancer: Finding a Needle in a Haystack 753 27.15 Complex Polysaccharides 755 Review 756 Review Questions 759 Paired Exercises, Additional Exercises Challenge Exercises 759 Answers to Practice Exercises 762 28 Lipids 763 28.1 Lipids: Hydrophobic Molecules 764 28.2 Classification of Lipids 765 28.3 Simple Lipids 765 28.4 Fats in Metabolism 770 28.5 Compound Lipids 771 28.6 Steroids 775 28.7 Hydrophobic Lipids and Biology 776 Stealth Drug Delivery 778 Health, Skin, and Transdermal Patches 782 Review 782 Review Questions 784 Paired Exercises, Additional Exercises Challenge Exercise 784 Answers to Practice Exercises 787 Review for Chapters 26--28 788 29 Amino Acids, Polypeptides, and Proteins 793 29.1 The Structure--Function Connection 794 29.2 The Nature of Amino Acids 795 29.3 Essential Amino Acids 797 29.4 D-Amino Acids and L-Amino Acids 798 29.5 Amphoterism 798 29.6 Formation of Polypeptides 800 Health, Growth Factors, and Cancer 801 29.7 Protein Structure 804 29.8 Protein Functions 807 29.9 Some Examples of Proteins and Their Structures 808 Molecular Machines 816 29.10 Loss of Protein Structure 817 29.11 Tests for Proteins and Amino Acids 819 29.12 Determination of the Primary Structure of Polypeptides 822 Review 824 Review Questions 827 Paired Exercises, Additional Exercises Challenge Exercise 827 Answers to Practice Exercises 830 30 Enzymes 832 30.1 Molecular Accelerators 833 30.2 Rates of Chemical Reactions 835 30.3 Enzyme Kinetics 836 30.4 Industrial-Strength Enzymes 838 30.5 Enzyme Active Site 840 Health and Cytochrome P450 841 30.6 Temperature and pH Effects on Enzyme Catalysis 843 30.7 Enzyme Regulation 844 Aspirin and Stroke: A Very Potent Enzyme Inhibitor 845 Review 846 Review Questions 848 Paired Exercises, Additional Exercises Challenge Exercise 848 Answers to Practice Exercises 850 31 Nucleic Acids and Heredity 851 31.1 Molecules of Heredity--A Link 852 31.2 Bases and Nucleosides 852 31.3 Nucleotides: Phosphate Esters 855 31.4 High-Energy Nucleotides 856 31.5 Polynucleotides; Nucleic Acids 857 31.6 Structure of DNA 859 31.7 DNA Replication 862 The Double Helix Revisited 865 Fingerprints in the Genes 866 31.8 RNA: Genetic Transcription 867 Health and RNA 870 31.9 The Genetic Code 871 31.10 Genes and Medicine 872 31.11 Biosynthesis of Proteins 874 31.12 Changing the Genome: Mutations and Genetic Engineering 877 Review 879 Review Questions 882 Paired Exercises, Additional Exercises Challenge Exercise 882 Answers to Practice Exercises 884 Review for Chapters 29--31 885 32 Nutrition 890 32.1 Nutrients 891 32.2 Diet 892 32.3 Energy in the Diet 892 32.4 Carbohydrates in the Diet 894 Health and Fiber 895 32.5 Fats in the Diet 896 32.6 Proteins in the Diet 897 32.7 Vitamins 897 32.8 Minerals 900 32.9 Water 901 32.10 Nutrition Content Labeling 901 32.11 Food Additives 903 32.12 A Balanced Diet 904 Longevity and Diet 905 32.13 Human Digestion 907 32.14 Absorption 911 32.15 Liver Function 911 Review 913 Review Questions 915 Paired Exercises, Additional Exercises Challenge Exercise 915 Answers to Practice Exercises 917 33 Bioenergetics 918 33.1 Energy Changes in Living Organisms 919 33.2 Metabolism and Cell Structure 920 33.3 Biological Oxidation--Reduction: Energy Delivery 921 33.4 Molecular Oxygen and Metabolism 925 33.5 High-Energy Phosphate Bonds 926 33.6 Phosphorylation: Energy Conversion 928 Health, Muscles, and Creatine 933 33.7 Photosynthesis 934 Review 935 Review Questions 936 Paired Exercises, Additional Exercises Challenge Exercise 937 Answers to Practice Exercises 938 34 Carbohydrate Metabolism 939 34.1 Metabolic Pathways 940 34.2 Exercise and Energy Metabolism 942 34.3 Carbohydrate Metabolism and Cooperation 942 34.4 Anaerobic Sequence 945 Health, Carbohydrate Metabolism, and Cancer 947 34.5 Citric Acid Cycle (Aerobic Sequence) 949 34.6 Gluconeogenesis 952 34.7 Overview of Complex Metabolic Pathways 953 34.8 Hormones 953 34.9 Blood Glucose and Hormones 956 Review 958 Review Questions 959 Paired Exercises, Additional Exercises Challenge Exercise 960 Answers to Practice Exercises 962 35 Metabolism of Lipids and Proteins 963 35.1 Metabolic Energy Sources: Organs Working Together for the Common Good 964 35.2 Fatty Acid Oxidation (Beta Oxidation) 965 Health and Abdominal Fat 968 35.3 Fat Storage and Utilization 969 35.4 Biosynthesis of Fatty Acids (Lipogenesis) 969 35.5 Ketone Bodies 971 Ketone Bodies and Low Carbohydrate Diets 972 35.6 Amino Acid Metabolism 973 35.7 Metabolic Nitrogen Fixation 973 35.8 Amino Acids and Metabolic Nitrogen Balance 975 35.9 Amino Acids and Nitrogen Transfer 977 35.10 Nitrogen Excretion and the Urea Cycle 978 35.11 Acetyl-CoA, a Central Molecule in Metabolism 981 Review 982 Review Questions 984 Paired Exercises, Additional Exercises Challenge Exercise 985 Answers to Practice Exercises 986 Review for Chapters 32--35 987 Appendixes I. Mathematical Review A-1 II. Using a Scientific Calculator A-11 III. Units of Measurement A-15 IV. Vapor Pressure of Water at Various Temperatures A-16 V. Solubility Table A-17 VI. Answers to Selected Exercises A-18 VII. Answers to Putting It Together Review Exercises A-34 Glossary G-1 Photo Credits PC-1 Index I-1