Chemistry for Today - General, Organic, and Biochemistry (9th Edition)

Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  NINTh EdITION Chemistry for Today General, Organic,...

Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  NINTh EdITION Chemistry for Today General, Organic, and Biochemistry Spencer L. Seager University of South Dakota Weber State University Michael R. Slabaugh University of South Dakota Weber State University Maren S. hansen West High School, Salt Lake City, UT Australia Brazil Mexico Singapore United Kingdom United States Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  This is an electronic version of the print textbook. Due to electronic rights restrictions, some third party content may be suppressed. Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. The publisher reserves the right to remove content from this title at any time if subsequent rights restrictions require it. 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To learn more about Cengage Learning Solutions, visit www.cengage.com Purchase any of our products at your local college store or at our preferred online store www.cengagebrain.com Printed in the United States of America Print Number: 01 Print Year: 2016 Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  To our grandchildren: Nate and Braden Barlow, Megan and Bradley Seager, and Andrew Gardner Alexander, Annie, Charlie, Christian, Elyse, Foster, Megan, and Mia Slabaugh, Addison, Hadyn, and Wyatt Hansen Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203 About the Authors Spencer L. Seager Spencer L. Seager retired from Weber State University in 2013 after serving for 52 years as a chemistry department faculty member. He served as department chairman from 1969 until 1993. He taught general and physical chemistry at the university. He was also active in projects designed to help improve chemistry and other science education in local elementary schools. He received his B.S. in chemistry and Ph.D. in physical chem- istry from the University of Utah. He currently serves as an adjunct professor at Weber State and the University of South Dakota where he teaches online courses in general chemistry, elementary organic chemistry, and elementary biochemistry. Michael R. Slabaugh Michael R. Slabaugh is an adjunct professor at the University of South Dakota and at Weber State University, where he teaches the yearlong sequence of general chemistry, organic chemistry, and biochemistry. He received his B.S. degree in chemistry from Pur- due University and his Ph.D. degree in organic chemistry from Iowa State University. His interest in plant alkaloids led to a year of postdoctoral study in biochemistry at Texas A&M University. His current professional interests are chemistry education and community involvement in science activities, particularly the State Science and Engi- neering Fair in Utah. He also enjoys the company of family, hiking in the mountains, and fishing the local streams. Maren S. Hansen Maren S. Hansen is a science teacher at West High School, where she teaches honors biology. She has also taught AP biology and biology in the International Baccalaure- ate Program. She received her B.A. and master of education degrees from Weber State University. Her professional interests have focused upon helping students participate in Science Olympiad and Science Fair. Other interests include adventure travel, mountain hiking, gardening, and the company of friends and family. She hopes to share her love of science with her two children. iv About the Authors Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203 Brief Contents Chapter 1 Chapter 13 Matter, Measurements, Alcohols, Phenols, and Ethers 424 and Calculations 2 Chapter 14 Chapter 2 Aldehydes and Ketones 458 Atoms and Molecules 46 Chapter 15 Chapter 3 Carboxylic Acids and Esters 488 Electronic Structure and the Periodic Law 72 Chapter 16 Amines and Amides 516 Chapter 4 Chapter 17 Forces between Particles 100 Carbohydrates 548 Chapter 5 Chapter 18 Chemical Reactions 144 Lipids 582 Chapter 6 Chapter 19 The States of Matter 174 Proteins 610 Chapter 7 Chapter 20 Solutions and Colloids 210 Enzymes 642 Chapter 8 Chapter 21 Reaction Rates and Equilibrium 250 Nucleic Acids and Protein Synthesis 668 Chapter 9 Chapter 22 Acids, Bases, and Salts 276 Nutrition and Energy for Life 702 Chapter 10 Chapter 23 Radioactivity and Nuclear Processes 322 Carbohydrate Metabolism 732 Chapter 11 Chapter 24 Organic Compounds: Alkanes 352 Lipid and Amino Acid Metabolism 760 Chapter 12 Chapter 25 Unsaturated Hydrocarbons 390 Body Fluids 788 Brief Contents v Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203 Contents Chapter 1 2.5 Isotopes and Atomic Weights 57 2.6 Avogadro’s Number: The Mole 58 Matter, Measurements, 2.7 The Mole and Chemical Formulas 63 and Calculations 2 Concept Summary 65 1.1 What Is Matter? 4 Key Terms and Concepts 66 1.2 Properties and Changes 5 Exercises 66 1.3 A Model of Matter 7 Additional Exercises 69 1.4 Classifying Matter 10 Chemistry for Thought 69 1.5 Measurement Units 13 Allied Health Exam Connection 70 1.6 The Metric System 14 Case Study 46 Chemistry Around us 2.1 Chemical Elements 1.7 Large and Small Numbers 19 in the Human Body 49 1.8 Significant Figures 22 Chemistry Around us 2.2 Looking at Atoms 51 1.9 Using Units in Calculations 27 ASk A phARMACIST 2.1 Uprooting Herbal Myths 54 1.10 Calculating Percentages 29 Chemistry tips for Living WeLL 2.1 1.11 Density 30 Take Care of Your Bones 55 Concept Summary 35 STudy SkILLS 2.1 Help with Mole Calculations 64 Key Terms and Concepts 36 Case Study Follow-up 65 Key Equations 36 Exercises 37 Chapter 3 Additional Exercises 43 Electronic Structure and the Chemistry for Thought 43 periodic Law 72 Allied Health Exam Connection 44 Case Study 2 3.1 The Periodic Law and Table 73 Chemistry Around us 1.1 A Central Science 5 3.2 Electronic Arrangements in Atoms 75 Chemistry Around us 1.2 Are Chemicals Getting 3.3 The Shell Model and Chemical a Bad Rap? 6 Properties 78 Chemistry Around us 1.3 Effects of Temperature 3.4 Electronic Configurations 80 on Body Function 19 3.5 Another Look at the Periodic Table 84 STudy SkILLS 1.1 Help with Calculations 30 3.6 Property Trends within the Periodic Chemistry tips for Living WeLL 1.1 Choose Table 89 Wisely for Health Information 32 Concept Summary 94 ASk AN ExpERT 1.1 Does food density matter when Key Terms and Concepts 95 you’re trying to lose weight? 34 Exercises 95 Case Study Follow-up 35 Additional Exercises 97 Chemistry for Thought 97 Chapter 2 Allied Health Exam Connection 98 Atoms and Molecules 46 Case Study 72 Chemistry tips for Living WeLL 3.1 Watch the 2.1 Symbols and Formulas 47 Salt 76 2.2 Inside the Atom 50 Chemistry Around us 3.1 A Solar 2.3 Isotopes 52 Future 83 2.4 Relative Masses of Atoms and Molecules 53 STudy SkILLS 3.1 The Convention Hotels Analogy 87 vi Contents Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  Chemistry Around us 3.2 Transition and 5.8 Energy and Reactions 157 Inner-Transition Elements in Your Smart Phone 89 5.9 The Mole and Chemical Equations 158 Case Study Follow-up 94 5.10 The Limiting Reactant 161 5.11 Reaction Yields 163 Chapter 4 Concept Summary 165 Forces between particles 100 Key Terms and Concepts 165 Key Equations 166 4.1 Noble Gas Configurations 101 Exercises 166 4.2 Ionic Bonding 103 Additional Exercises 170 4.3 Ionic Compounds 105 Chemistry for Thought 170 4.4 Naming Binary Ionic Compounds 108 Allied Health Exam Connection 171 4.5 The Smallest Unit of Ionic Compounds 110 Case Study 144 4.6 Covalent Bonding 111 Chemistry tips for Living WeLL 5.1 Add Color 4.7 Polyatomic Ions 116 to Your Diet 156 4.8 Shapes of Molecules and Polyatomic Ions 118 Chemistry Around us 5.1 Teeth 4.9 The Polarity of Covalent Molecules 122 Whitening 159 4.10 More about Naming Compounds 126 Chemistry Around us 5.2 Electric Cars 162 STudy SkILLS 5.1 Help with Oxidation Numbers 163 4.11 Other Interparticle Forces 129 Case Study Follow-up 164 Concept Summary 134 Key Terms and Concepts 135 Exercises 136 Chapter 6 Additional Exercises 140 The States of Matter 174 Chemistry for Thought 140 6.1 Observed Properties of Matter 176 Allied Health Exam Connection 141 6.2 The Kinetic Molecular Theory of Matter 178 Case Study 100 6.3 The Solid State 179 Chemistry tips for Living WeLL 4.1 Consider the Mediterranean Diet 107 6.4 The Liquid State 180 Chemistry Around us 4.1 Water: One of Earth’s 6.5 The Gaseous State 180 Special Compounds 113 6.6 The Gas Laws 181 ASk A phARMACIST 4.1 Are All Iron Preparations 6.7 Pressure, Temperature, and Volume Created Equal? 123 Relationships 184 STudy SkILLS 4.1 Help with Polar and Nonpolar 6.8 The Ideal Gas Law 189 Molecules 127 6.9 Dalton’s Law 191 Chemistry Around us 4.2 Ozone: Good up High, Bad Nearby 131 6.10 Graham’s Law 192 Case Study Follow-up 134 6.11 Changes in State 192 6.12 Evaporation and Vapor Pressure 193 6.13 Boiling and the Boiling Point 195 Chapter 5 6.14 Sublimation and Melting 196 Chemical Reactions 144 6.15 Energy and the States of Matter 197 5.1 Chemical Equations 145 Concept Summary 202 5.2 Types of Reactions 147 Key Terms and Concepts 203 5.3 Redox Reactions 148 Key Equations 203 5.4 Decomposition Reactions 151 Exercises 203 5.5 Combination Reactions 152 Additional Exercises 207 5.6 Replacement Reactions 153 Chemistry for Thought 207 5.7 Ionic Equations 155 Allied Health Exam Connection 207 Contents vii Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  Case Study 174 8.5 Factors That Influence Reaction Rates 258 Chemistry tips for Living WeLL 6.1 Get an 8.6 Chemical Equilibrium 260 Accurate Blood Pressure Reading 184 8.7 The Position of Equilibrium 262 ASk A phARMACIST 6.1 Zinc for Colds? 188 8.8 Factors That Influence Equilibrium Chemistry Around us 6.1 Air Travel 195 Position 264 Chemistry Around us 6.2 Therapeutic Uses Concept Summary 267 of Oxygen Gas 198 Key Terms and Concepts 268 STudy SkILLS 6.1 Which Gas Law to Use 200 Key Equations 268 Case Study Follow-up 201 Exercises 268 Additional Exercises 273 Chapter 7 Chemistry for Thought 273 Solutions and Colloids 210 Allied Health Exam Connection 273 Case Study 250 7.1 Physical States of Solutions 211 ASk A phARMACIST 8.1 Energy for Sale 255 7.2 Solubility 212 Chemistry tips for Living WeLL 8.1 Use Your 7.3 The Solution Process 216 Phone to Help You Stay Healthy 261 7.4 Solution Concentrations 220 Chemistry Around us 8.1 Why “Cold” Does Not 7.5 Solution Preparation 224 Exist 265 7.6 Solution Stoichiometry 227 STudy SkILLS 8.1 Le Châtelier’s Principle in Everyday 7.7 Solution Properties 229 Life 267 Case Study Follow-up 267 7.8 Colloids 235 7.9 Dialysis 238 Concept Summary 241 Chapter 9 Key Terms and Concepts 241 Key Equations 242 Acids, Bases, and Salts 276 Exercises 242 9.1 The Arrhenius Theory 277 Additional Exercises 247 9.2 The Brønsted Theory 278 Chemistry for Thought 247 9.3 Naming Acids 279 Allied Health Exam Connection 247 9.4 The Self-Ionization of Water 281 Case Study 210 9.5 The pH Concept 283 Chemistry tips for Living WeLL 7.1 Stay 9.6 Properties of Acids 286 Hydrated 222 9.7 Properties of Bases 290 STudy SkILLS 7.1 Getting Started with Molarity 9.8 Salts 291 Calculations 234 9.9 The Strengths of Acids and Bases 294 Chemistry Around us 7.1 Health Drinks 237 9.10 Analyzing Acids and Bases 300 Chemistry Around us 7.2 CO2 Emissions: A Blanket around the Earth 239 9.11 Titration Calculations 302 Case Study Follow-up 240 9.12 Hydrolysis Reactions of Salts 304 9.13 Buffers 305 Concept Summary 310 Chapter 8 Key Terms and Concepts 311 Reaction Rates and Equilibrium 250 Key Equations 311 8.1 Spontaneous and Nonspontaneous Exercises 311 Processes 251 Additional Exercises 318 8.2 Reaction Rates 253 Chemistry for Thought 318 8.3 Molecular Collisions 254 Allied Health Exam Connection 319 8.4 Energy Diagrams 257 Case Study 276 viii Contents Copyright 2018 Cengage Learning. 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WCN 02-200-203  Chemistry Around us 9.1 Sinkholes 294 11.5 Alkane Structures 361 STudy SkILLS 9.1 Writing Reactions of Acids 298 11.6 Conformations of Alkanes 365 Chemistry tips for Living WeLL 9.1 Beware of 11.7 Alkane Nomenclature 367 Heartburn 299 11.8 Cycloalkanes 373 ASk AN ExpERT 9.1 Does diet play a role in peptic ulcer 11.9 The Shape of Cycloalkanes 375 disease? 308 Case Study Follow-up 309 11.10 Physical Properties of Alkanes 378 11.11 Alkane Reactions 380 Concept Summary 381 Chapter 10 Key Terms and Concepts 382 Radioactivity and Nuclear Key Equations 382 processes 322 Exercises 382 Additional Exercises 388 10.1 Radioactive Nuclei 323 Chemistry for Thought 388 10.2 Equations for Nuclear Reactions 325 Allied Health Exam Connection 388 10.3 Isotope Half-Life 328 Case Study 352 10.4 The Health Effects of Radiation 329 STudy SkILLS 11.1 Changing Gears for Organic 10.5 Measurement Units for Radiation 331 Chemistry 356 10.6 Medical Uses of Radioisotopes 334 ASk AN ExpERT 11.1 Is organic food worth the 10.7 Nonmedical Uses of Radioisotopes 335 price? 362 10.8 Induced Nuclear Reactions 337 Chemistry Around us 11.1 Fracking Oil Wells 376 10.9 Nuclear Energy 340 Chemistry tips for Living WeLL 11.1 Take Care of Dry Skin 378 Concept Summary 345 Chemistry Around us 11.2 Reducing Your Key Terms and Concepts 345 Carbon Footprint 380 Key Equations 346 Case Study Follow-up 381 Exercises 346 Additional Exercises 348 Chapter 12 Chemistry for Thought 348 Allied Health Exam Connection 349 unsaturated hydrocarbons 390 Case Study 322 12.1 The Nomenclature of Alkenes 392 Chemistry Around us 10.1 Radiation Exposure 12.2 The Geometry of Alkenes 394 in Modern Life 332 12.3 Properties of Alkenes 398 Chemistry tips for Living WeLL 10.1 Check the Radon Level in Your Home 336 12.4 Addition Polymers 403 ASk A phARMACIST 10.1 Medications to Avoid on Test 12.5 Alkynes 406 Day 344 12.6 Aromatic Compounds and the Benzene Case Study Follow-up 344 Structure 408 12.7 The Nomenclature of Benzene Derivatives 410 Chapter 11 12.8 Properties and Uses of Aromatic Organic Compounds: Alkanes 352 Compounds 414 Concept Summary 417 11.1 Carbon: The Element of Organic Key Terms and Concepts 417 Compounds 353 Key Reactions 418 11.2 Organic and Inorganic Compounds Compared 354 Exercises 418 11.3 Bonding Characteristics and Isomerism 356 Additional Exercises 422 11.4 Functional Groups: The Organization Chemistry for Thought 422 of Organic Chemistry 359 Allied Health Exam Connection 423 Contents ix Copyright 2018 Cengage Learning. 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WCN 02-200-203  Case Study 390 Chapter 14 Chemistry Around us 12.1 Three-Dimensional Printers 396 Aldehydes and ketones 458 STudy SkILLS 12.1 Keeping a Reaction Card File 402 14.1 The Nomenclature of Aldehydes STudy SkILLS 12.2 A Reaction Map for Alkenes 404 and Ketones 460 Chemistry Around us 12.2 Polycarbonate—The 14.2 Physical Properties 463 Lucky Polymer 406 14.3 Chemical Properties 465 hoW reACtions oCCur 12.1 The Hydration of Alkenes: An Addition Reaction 409 14.4 Important Aldehydes and Ketones 476 Chemistry tips for Living WeLL 12.1 Think Concept Summary 479 before Getting Brown 412 Key Terms and Concepts 479 ASk A phARMACIST 12.1 Controlled Substances 413 Key Reactions 479 Chemistry Around us 12.3 Graphene 415 Exercises 480 Case Study Follow-up 416 Additional Exercises 485 Chemistry for Thought 485 Chapter 13 Allied Health Exam Connection 486 Alcohols, phenols, and Ethers 424 Case Study 458 Chemistry Around us 14.1 Faking 13.1 The Nomenclature of Alcohols a Tan 464 and Phenols 426 hoW reACtions oCCur 14.1 Hemiacetal 13.2 Classification of Alcohols 428 Formation 471 13.3 Physical Properties of Alcohols 429 STudy SkILLS 14.1 A Reaction Map for Aldehydes 13.4 Reactions of Alcohols 431 and Ketones 472 13.5 Important Alcohols 436 Chemistry Around us 14.2 Vanilloids: Hot Relief from Pain 474 13.6 Characteristics and Uses of Phenols 440 Chemistry tips for Living WeLL 14.1 Get the 13.7 Ethers 443 Right Dose of Exercise 476 13.8 Properties of Ethers 444 Case Study Follow-up 478 13.9 Thiols 445 13.10 Polyfunctional Compounds 448 Concept Summary 449 Chapter 15 Key Terms and Concepts 450 Carboxylic Acids and Esters 488 Key Reactions 450 15.1 The Nomenclature of Carboxylic Acids 490 Exercises 451 15.2 Physical Properties of Carboxylic Acids 491 Additional Exercises 455 15.3 The Acidity of Carboxylic Acids 493 Chemistry for Thought 455 15.4 Salts of Carboxylic Acids 494 Allied Health Exam Connection 456 15.5 Carboxylic Esters 496 Case Study 424 hoW reACtions oCCur 13.1 The Dehydration of 15.6 The Nomenclature of Esters 500 an Alcohol 433 15.7 Reactions of Esters 502 STudy SkILLS 13.1 A Reaction Map for Alcohols 438 15.8 Esters of Inorganic Acids 505 Chemistry Around us 13.1 Alcohol and Concept Summary 508 Antidepressants Don’t Mix 439 Key Terms and Concepts 509 ASk A phARMACIST 13.1 Marijuana: A Gateway Key Reactions 509 Drug 441 Exercises 510 Chemistry tips for Living WeLL 13.1 Take Advantage of Hand Sanitizers 442 Additional Exercises 514 Chemistry Around us 13.2 General Chemistry for Thought 514 Anesthetics 446 Allied Health Exam Connection 514 Case Study Follow-up 449 Case Study 488 x Contents Copyright 2018 Cengage Learning. 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WCN 02-200-203  Chemistry tips for Living WeLL 15.1 Consider 17.4 Monosaccharides 559 Low-Dose Aspirin 503 17.5 Properties of Monosaccharides 560 STudy SkILLS 15.1 A Reaction Map for Carboxylic 17.6 Important Monosaccharides 566 Acids 504 17.7 Disaccharides 567 hoW reACtions oCCur 15.1 Ester Saponification 505 17.8 Polysaccharides 571 Chemistry Around us 15.1 Nitroglycerin in Concept Summary 576 Dynamite and in Medicine 507 Key Terms and Concepts 576 Case Study Follow-up 508 Key Reactions 576 Exercises 577 Chapter 16 Additional Exercises 580 Chemistry for Thought 580 Amines and Amides 516 Allied Health Exam Connection 580 16.1 Classification of Amines 517 Case Study 548 16.2 The Nomenclature of Amines 518 Chemistry Around us 17.1 Sugar-Free Foods and Diabetes 564 16.3 Physical Properties of Amines 520 STudy SkILLS 17.1 Biomolecules: A New Focus 568 16.4 Chemical Properties of Amines 521 Chemistry tips for Living WeLL 17.1 Put Fiber 16.5 Amines as Neurotransmitters 529 into Snacks and Meals 569 16.6 Other Biologically Important Amines 532 ASk AN ExpERT 17.1 Is high-fructose corn syrup worse 16.7 The Nomenclature of Amides 535 for your health than table sugar? 574 16.8 Physical Properties of Amides 536 Case Study Follow-up 575 16.9 Chemical Properties of Amides 537 Concept Summary 540 Chapter 18 Key Terms and Concepts 540 Key Reactions 540 Lipids 582 Exercises 541 18.1 Classification of Lipids 584 Additional Exercises 545 18.2 Fatty Acids 584 Chemistry for Thought 545 18.3 The Structure of Fats and Oils 587 Allied Health Exam Connection 546 18.4 Chemical Properties of Fats and Oils 589 Case Study 516 18.5 Waxes 592 ASk AN ExpERT 16.1 Does caffeine help with weight 18.6 Phosphoglycerides 592 loss? 519 18.7 Sphingolipids 594 ASk A phARMACIST 16.1 A Wake-Up Call for Treating Insomnia 524 18.8 Biological Membranes 596 Chemistry Around us 16.1 Aspirin 18.9 Steroids 598 Substitutes 528 18.10 Steroid Hormones 601 STudy SkILLS 16.1 A Reaction Map for Amines 531 18.11 Prostaglandins 604 Chemistry tips for Living WeLL 16.1 Try a Little Concept Summary 605 Chocolate 534 Key Terms and Concepts 606 Case Study Follow-up 539 Key Reactions 606 Exercises 607 Chapter 17 Additional Exercises 608 Chemistry for Thought 608 Carbohydrates 548 Allied Health Exam Connection 609 17.1 Classes of Carbohydrates 550 Case Study 582 17.2 The Stereochemistry of Carbohydrates 551 STudy SkILLS 18.1 A Reaction Map for 17.3 Fischer Projections 555 Triglycerides 592 Contents xi Copyright 2018 Cengage Learning. 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WCN 02-200-203  Chemistry Around us 18.1 Biofuels Move into 20.4 The Mechanism of Enzyme Action 649 the Kitchen 599 20.5 Enzyme Activity 650 ASk AN ExpERT 18.1 How significantly can diet really 20.6 Factors Affecting Enzyme Activity 651 lower cholesterol? 600 20.7 Enzyme Inhibition 653 Chemistry tips for Living WeLL 18.1 Consider Olive Oil 603 20.8 The Regulation of Enzyme Activity 658 Case Study Follow-up 605 20.9 Medical Application of Enzymes 661 Concept Summary 663 Key Terms and Concepts 664 Chapter 19 Key Reactions 664 proteins 610 Exercises 664 19.1 The Amino Acids 611 Additional Exercises 665 19.2 Zwitterions 614 Chemistry for Thought 666 19.3 Reactions of Amino Acids 616 Allied Health Exam Connection 666 Case Study 642 19.4 Important Peptides 619 Chemistry tips for Living WeLL 20.1 Cut Back 19.5 Characteristics of Proteins 621 on Processed Meat 646 19.6 The Primary Structure of Proteins 625 ASk A phARMACIST 20.1 Treatment Options for 19.7 The Secondary Structure of Proteins 626 the Common Cold 648 19.8 The Tertiary Structure of Proteins 629 Chemistry Around us 20.1 Enzyme Discovery 19.9 The Quaternary Structure of Proteins 631 Heats Up 654 19.10 Protein Hydrolysis and Denaturation 633 Chemistry Around us 20.2 No Milk Please 656 Concept Summary 635 STudy SkILLS 20.1 A Summary Chart of Enzyme Key Terms and Concepts 636 Inhibitors 660 Key Reactions 636 Case Study Follow-up 663 Exercises 637 Additional Exercises 639 Chemistry for Thought 639 Chapter 21 Allied Health Exam Connection 640 Nucleic Acids and protein Case Study 610 ASk AN ExpERT 19.1 Can a higher-protein diet help me Synthesis 668 lose weight? 617 21.1 Components of Nucleic Acids 670 Chemistry tips for Living WeLL 19.1 Go for 21.2 The Structure of DNA 672 the Good Grains 620 21.3 DNA Replication 676 Chemistry Around us 19.1 Alzheimer’s Disease 624 21.4 Ribonucleic Acid (RNA) 680 Chemistry Around us 19.2 A Milk Primer 629 21.5 The Flow of Genetic Information 683 STudy SkILLS 19.1 Visualizing Protein Structure 631 21.6 Transcription: RNA Synthesis 684 ASk A phARMACIST 19.1 Who Really Needs Gluten- 21.7 The Genetic Code 686 Free Food? 633 21.8 Translation and Protein Synthesis 689 Case Study Follow-up 635 21.9 Mutations 692 21.10 Recombinant DNA 692 Chapter 20 Concept Summary 697 Key Terms and Concepts 698 Enzymes 642 Exercises 698 20.1 General Characteristics of Enzymes 643 Additional Exercises 700 20.2 Enzyme Nomenclature and Classification 645 Chemistry for Thought 700 20.3 Enzyme Cofactors 647 Allied Health Exam Connection 700 xii Contents Copyright 2018 Cengage Learning. 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WCN 02-200-203  Case Study 668 Chapter 23 Chemistry Around us 21.1 The Clone Wars 681 Carbohydrate Metabolism 732 Chemistry Around us 21.2 Is There a DNA 23.1 The Digestion of Carbohydrates 733 Checkup in Your Future? 686 23.2 Blood Glucose 734 STudy SkILLS 21.1 Remembering Key Words 688 23.3 Glycolysis 734 Chemistry Around us 21.3 Stem Cell Research 690 23.4 The Fates of Pyruvate 738 Chemistry Around us 21.4 DNA and the Crime 23.5 The Citric Acid Cycle 740 Scene 694 23.6 The Electron Transport Chain 743 Chemistry tips for Living WeLL 21.1 Reduce 23.7 Oxidative Phosphorylation 743 Your Chances for Developing Cancer 696 23.8 The Complete Oxidation of Glucose 745 Case Study Follow-up 697 23.9 Glycogen Metabolism 747 23.10 Gluconeogenesis 749 23.11 The Hormonal Control of Carbohydrate Chapter 22 Metabolism 751 Nutrition and Energy Concept Summary 753 for Life 702 Key Terms and Concepts 754 Key Reactions 754 22.1 Nutritional Requirements 703 Exercises 755 22.2 The Macronutrients 705 Additional Exercises 757 22.3 Micronutrients I: Vitamins 708 Chemistry for Thought 757 22.4 Micronutrients II: Minerals 712 Allied Health Exam Connection 758 22.5 The Flow of Energy in the Biosphere 713 Case Study 732 22.6 Metabolism and an Overview ASk AN ExpERT 23.1 How can we avoid energy of Energy Production 715 crashes? 736 22.7 ATP: The Primary Energy Carrier 718 Chemistry Around us 23.1 Lactate 22.8 Important Coenzymes in the Common Accumulation 742 Catabolic Pathway 722 STudy SkILLS 23.1 Key Numbers for ATP Concept Summary 727 Calculations 748 Key Terms and Concepts 728 Chemistry Around us 23.2 What Is the Best Weight-Loss Strategy? 750 Key Reactions 728 Chemistry tips for Living WeLL 23.1 Choose Exercises 729 Complex Carbohydrates 752 Additional Exercises 730 Case Study Follow-up 753 Chemistry for Thought 731 Allied Health Exam Connection 731 Case Study 702 Chapter 24 Chemistry Around us 22.1 The 10 Most Lipid and Amino Dangerous Foods to Eat While Driving 710 Chemistry tips for Living WeLL 22.1 Select a Acid Metabolism 760 Heart-Healthful Diet 711 24.1 Blood Lipids 761 ASk A phARMACIST 22.1 Sport Supplements: 24.2 Fat Mobilization 765 Where Is My Edge? 716 24.3 Glycerol Metabolism 766 STudy SkILLS 22.1 Bioprocesses 720 24.4 The Oxidation of Fatty Acids 766 Chemistry Around us 22.2 Calorie Language 721 24.5 The Energy from Fatty Acids 769 ASk AN ExpERT 6.1 Is it better to take a fiber 24.6 Ketone Bodies 770 supplement or to eat fiber-fortified foods? 726 24.7 Fatty Acid Synthesis 772 Case Study Follow-up 727 24.8 Amino Acid Metabolism 773 Contents xiii Copyright 2018 Cengage Learning. 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WCN 02-200-203 24.9 Amino Acid Catabolism: The Fate of the 25.4 The Constituents of Urine 796 Nitrogen Atoms 774 25.5 Fluid and Electrolyte Balance 797 24.10 Amino Acid Catabolism: The Fate of the 25.6 Acid–Base Balance 799 Carbon Skeleton 778 25.7 Buffer Control of Blood pH 799 24.11 Amino Acid Biosynthesis 781 25.8 Respiratory Control of Blood pH 800 Concept Summary 782 25.9 Urinary Control of Blood pH 800 Key Terms and Concepts 783 25.10 Acidosis and Alkalosis 801 Key Reactions 784 Concept Summary 804 Exercises 785 Key Terms and Concepts 805 Additional Exercises 786 Key Reactions 805 Chemistry for Thought 786 Exercises 805 Allied Health Exam Connection 787 Additional Exercises 806 Case Study 760 Chemistry for Thought 807 ASk AN ExpERT 24.1 Are certain foods better for the brain? 764 Allied Health Exam Connection 807 STudy SkILLS 24.1 Key Numbers for ATP Case Study 788 Calculations 771 ASk A phARMACIST 25.1 Performance-Enhancing Chemistry tips for Living WeLL 24.1 Pick the Drugs 792 Right Fats 776 Chemistry tips for Living WeLL 25.1 Select the Chemistry Around us 24.1 Phenylketonuria Right Pre-Exercise Foods 794 (PKU) 779 Chemistry Around us 25.1 Pulse Chemistry Around us 24.2 Phenylalanine and Oximetry 798 Diet Foods 780 Case Study Follow-up 804 Case Study Follow-up 782 Appendix A The International System Chapter 25 of Measurements A-1 Appendix B Answers to Even-Numbered Body Fluids 788 End-of-Chapter Exercises B-1 25.1 A Comparison of Body Fluids 789 Appendix C Solutions to Learning Checks C-1 25.2 Oxygen and Carbon Dioxide Transport 790 glossary G-1 25.3 Chemical Transport to the Cells 795 index I-1 xiv Contents Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203 preface the image of Chemistry We, as authors, are pleased that the acceptance of the previous eight editions of this text- book by students and their teachers has made it possible to publish this ninth edition. In the earlier editions, we expressed our concern about the negative image of chemistry held by many of our students, and their genuine fear of working with chemicals in the labora- tory. Unfortunately, this negative image not only persists, but seems to be intensifying. Reports in the media related to chemicals or to chemistry continue to be primarily nega- tive, and in many cases seem to be designed to increase the fear and concern of the general public. With this edition, we continue to hope that those who use this book will gain a more positive understanding and appreciation of the important contributions that chemis- try makes in their lives. theme and organization This edition continues the theme of the positive and useful contributions made by chemistry in our world. This text is designed to be used in either a two-semester or three-quarter course of study that provides an introduction to general chemistry, organic chemistry, and biochemistry. Most students who take such courses are majoring in nursing, other health professions, or the life sciences, and consider biochemistry to be the most relevant part of the course of study. However, an understanding of biochemistry depends upon a sound background in organic chemistry, which in turn depends upon a good foundation in general chemistry. We have attempted to present the general and organic chemistry in sufficient depth and breadth to make the biochemistry understandable. The decisions about what to include and what to omit from the text were based on our combined 75-plus years of teaching, input from numerous reviewers and adopters, and our philosophy that a textbook functions as a personal tutor to each student. In the role of a personal tutor, a text must be more than just a collection of facts, data, and exercises. It should also help students relate to the material they are studying, carefully guide them through more difficult material, provide them with interesting and relevant examples of chemistry in their lives, and become a reference and a resource that they can use in other courses or their professions. new to this edition In this ninth edition of the text, we have some exciting new features, including Ask a Phar- macist boxes written by Marvin Orrock and Chemistry Tips for Living Well. We have also retained features that received a positive reception from our own students, the students of other adopters, other teachers, and reviewers. The retained features are Case Studies, which begin each chapter, including 8 new to this edition; 45 Chemistry Around Us boxes, includ- ing 19 new to this edition; 23 Study Skills boxes; 4 How Reactions Occur boxes; and 10 Ask an Expert boxes. The 12 Ask a Pharmacist boxes reflect coverage of both prescription and nonprescription health-related products. The 25 Chemistry Tips for Living Well contain cur- rent chemistry-related health issues and suggestions. In addition, approximately 10% of the end-of-chapter exercises have been changed. Also new to this edition are many new photographs and updated art to further enhance student comprehension of key concepts, processes, and preparation. Preface xv Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  Revision Summary of Ninth Edition: Chapter 1: New Case Study New Case Study Follow-up Several revised figures New photography New Ask an Expert: Does Food Density Matter When You’re Trying to Lose Weight? New Chemistry Around Us: Are Chemicals Getting a Bad Rap? New Chemistry Tips for Living Well: Choose Wisely for Health Information 10% new Exercises Chapter 2: Several revised figures New photography Updated element table New Chemistry Around Us: Chemical Elements in the Human Body New Ask a Pharmacist: Uprooting Herbal Myths New Chemistry Tips for Living Well: Take Care of Your Bones 10% new Exercises Chapter 3: Several revised figures New photography New Chemistry Tips for Living Well: Watch the Salt New Chemistry Around Us: A Solar Future New Chemistry Around Us: Transition and Inner-Transition Elements in Your Smart Phone 10% new Exercises Chapter 4: Several revised figures New photography New Ask a Pharmacist: Are All Iron Preparations Created Equal? New Chemistry Tips for Living Well: Consider the Mediterranean Diet New Chemistry Around Us: Ozone: Good up High, Bad Nearby 10% new Exercises Chapter 5: New Case Study New Case Study Follow-up Several revised figures New photography New Chemistry Tips for Living Well: Add Color to Your Diet New Chemistry Around Us: Teeth Whitening New Chemistry Around Us: Electric Cars 10% new Exercises Chapter 6: Several revised figures New photography New Ask a Pharmacist: Zinc for Colds? New Chemistry Tips for Living Well: Get an Accurate Blood Pressure Reading New Chemistry Around Us: Air Travel 10% new Exercises xvi Preface Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203 Chapter 7: New Case Study New Case Study Follow-up Several revised figures New photography New Chemistry Around Us: Health Drinks New Chemistry Around Us: CO Emissions: A Blanket around the Earth 2 New Chemistry Tips for Living Well: Stay Hydrated 10% new Exercises Chapter 8: Several revised figures New photography New Ask a Pharmacist: Energy for Sale New Chemistry Around Us: Why “Cold” Does Not Exist New Chemistry Tips for Living Well: Use Your Phone to Help You Stay Healthy 10% new Exercises Chapter 9: Several revised figures New photography New Chemistry Tips for Living Well: Beware of Heartburn New Chemistry Around Us: Sinkholes 10% new Exercises Chapter 10: New Case Study New Case Study Follow-up Several revised figures New photography New Ask a Pharmacist: Medications to Avoid on Test Day New Chemistry Tips for Living Well: Check the Radon Level in Your Home 10% new Exercises Chapter 11: Several revised figures New photography New Chemistry Around Us: Fracking Oil Wells New Chemistry Around Us: Reducing Your Carbon Footprint New Chemistry Tips for Living Well: Take Care of Dry Skin 10% new Exercises Chapter 12: Several revised figures New photography New Ask a Pharmacist: Controlled Substances New Chemistry Tips for Living Well: Think before Getting Brown New Chemistry Around Us: Three-Dimensional Printers New Chemistry Around Us: Polycarbonate—The Lucky Polymer New Chemistry Around Us: Graphene 10% new Exercises Chapter 13: Several revised figures New photography Preface xvii Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  New Ask a Pharmacist: Marijuana: A Gateway Drug New Chemistry Tips for Living Well: Take Advantage of Hand Sanitizers 10% new Exercises Chapter 14: Several revised figures New photography New Chemistry Tips for Living Well: Get the Right Dose of Exercise 10% new Exercises Chapter 15: New Case Study New Case Study Follow-up Several revised figures New photography New Chemistry Tips for Living Well: Consider Low-Dose Aspirin 10% new Exercises Chapter 16: Several revised figures New photography New Ask a Pharmacist: A Wake-Up Call for Treating Insomnia New Chemistry Tips for Living Well: Try a Little Chocolate 10% new Exercises Chapter 17: Several revised figures New photography New Chemistry Tips for Living Well: Put Fiber into Snacks and Meals 10% new Exercises Chapter 18: Several revised figures New photography New Chemistry Tips for Living Well: Consider Olive Oil New Chemistry Around Us: Biofuels Move into the Kitchen 10% new Exercises Chapter 19: New Case Study New Case Study Follow-up Several revised figures New photography New Ask a Pharmacist: Who Really Needs Gluten-Free Food? New Chemistry Around Us: A Milk Primer New Chemistry Tips for Living Well: Go for the Good Grains 10% new Exercises Chapter 20: Several revised figures New photography New Ask a Pharmacist: Treatment Options for the Common Cold New Chemistry Around Us: No Milk Please New Chemistry Tips for Living Well: Cut Back on Processed Meat 10% new Exercises xviii Preface Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203 Chapter 21: New Case Study New Case Study Follow-up Several revised figures New photography New Chemistry Tips for Living Well: Reduce Your Chances for Developing Cancer 10% new Exercises Chapter 22: Several revised figures New photography New Ask a Pharmacist: Sports Supplements: Where Is My Edge? New Chemistry Tips for Living Well: Select a Heart-Healthful Diet 10% new Exercises Chapter 23: Several revised figures New photography New Chemistry Tips for Living Well: Choose Complex Carbohydrates 10% new Exercises Chapter 24: New Case Study New Case Study Follow-up New photography New Chemistry Tips for Living Well: Pick the Right Fats 10% new Exercises Chapter 25: New photography New Ask a Pharmacist: Performance-Enhancing Drugs New Chemistry Tips for Living Well: Select the Right Pre-Exercise Foods 10% new Exercises features Each chapter has features especially designed Case Study Purpose: The case study scenarios introduce diverse situations that a health care to help students study effectively, as well as professional might encounter. Their purpose is to stimulate inquiry; for that reason, organize, understand, and enjoy the material we’ve placed them at the beginning of each chapter. Vocabulary and scenarios may be in the course. unfamiliar, but our intention is to stimulate questions and to pique curiosity. Medicine Case Studies. These scenarios introduce has long been described as an art as well as a science. The questions raised by these you the students to diverse situations a health case studies rarely have a single correct answer. With the knowledge that you gain care professional might encounter. The pur- from this text, and your future training, acceptable answers to the questions raised in pose of the case studies is to stimulate in- our scenarios will become apparent. quiry; for that reason, we’ve placed them at Disclaimer: Some of the case studies are based on real-life situations. In the beginning of each chapter of the book. such cases, names have been changed to protect the individual’s anonymity. Vocabulary and scenarios may be unfamiliar to you who are studying these course materi- als, but our intent is to raise questions and pique your curiosity. Medicine has long been described as an art. The questions raised by these case studies rarely have a single cor- rect answer. With the knowledge that you gain from this text and your future training, Preface xix Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203  acceptable answers to the questions raised in our scenarios will become apparent. A Case Study Follow-up to each Case Study can be found at the end of each chapter before the Concept Summary. Chapter Outlines and Learning Objectives. At the beginning of each chapter, a list of learning objectives provides students with a convenient overview of what they should gain by studying the chapter. In order to help students navigate through each chap- ter and focus on key concepts, these objectives are repeated at the beginning of the section in which the applicable information is discussed. The objectives are referred to again in the concept summary at the end of each chapter along with one or two suggested end-of- chapter exercises. By working the suggested exercises, students get a quick indication of how well they have met the stated learning objectives. Thus, students begin each chapter with a set of objectives and end with an indication of how well they satisfied the objectives. key Terms. Identified within the text by the use of bold type, key terms are defined in the margin near the place where they are introduced. Students reviewing a chapter can quickly identify the important concepts on each page with this marginal glossary. A full glossary of key terms and concepts appears at the end of the text. Ask a pharmacist. These boxed features written by Marvin Orrock, Pharm.D., con- tain useful information about health-related products that are readily available to consum- ers with or without a prescription. The information in each box provides a connection between the chemical behavior of the product and its effect on the body. ASK A PHARMACIST 12.1 Controlled Substances United States, or a currently accepted medical use with se- vere restrictions. Abuse of the substance might lead to severe So what are controlled substance, anyway, and why do we psychological or physical dependence (e.g., Percocet, De- have them? Before we answer those questions, let’s briefly merol, Ritalin). review the major legislation that pertains to products used Schedule III: The substance has a potential for abuse less as medicines. Prior to the 1900s there were no governmen- than the compounds in Schedules I and II. The substance has tal regulations on foods or drugs. As a result, some products a currently accepted medical use for treatment in the United were contaminated and some not labeled accurately. Conse- States. Abuse of the substance might lead to moderate or quently, the U.S. Congress passed the Pure Food and Drug low physical dependence or high psychological dependence Act of 1906. It proved to be helpful, but opiates and cocaine (e.g.,Tylenol with codeine used for pain, anabolic steroids). were not regulated. A significant percentage of the popula- Schedule IV: The substance has a low potential for abuse tion became addicted, and many deaths were attributed to the relative to the compounds in Schedule III. The substance has use of products that were “pure” and “labeled” correctly but a currently accepted medical use for treatment in the United still contained addicting materials. In 1914 the Harrison Act States. Abuse of the substance might lead to limited physical was passed. It regulated heroin and cocaine sales. During the dependence or psychological dependence relative to the sub- Chemistry Around us. These boxed features present everyday applications of chemistry that emphasize in a real way the important role of chemistry in our lives. Thirty percent of these are new to this edition and emphasize health-related applications of chemistry. Chemistry Tips for Living Well. These boxed features contain current chemistry- related health issues such as “Add Color to Your Diet,” and suggestions for maintaining good health such as “Consider the Mediterranean Diet,” “Cut Back on Processed Meat,” and “Try a Little Chocolate.” ChemisTry Tips for Living WeLL 14.1 Get the Right dose of exercise Experts agree that exercise is one of the best preventative times the recommended amount), health benefits are com- “medicines” available. It increases energy, stamina, and parable to those achieved by people who merely meet the one’s sense of well-being. In the long term it also reduces minimum requirements. In other words, many extra hours the risk of premature death from cardiovascular disease. Put of exercise do not equate to huge gains in longevity. On the simply, it makes you feel better and live longer. We expect other hand, many times the recommended exercise level is medicines to make us feel better when we are ill. But exer- not considered to be harmful. It is difficult to overdose on cise acts as a powerful medicine to prevent illness. How do moderate exercise. you know what the proper dose is? Do you need to exercise Intensity, as well as frequency, should be considered on a daily basis or will a weekly dose provide the desired when calculating the ideal exercise dose. People who spend health benefits? Just how little can you get away with and part of their daily exercise time in vigorous activity, rather stay healthy? than moderate activity alone (e.g., running instead of walk- Researchers arrive at the proper dose by examining ing) reap additional health benefits. People who spent up to health survey data that includes the exercise habits of sev 30% of their exercise time in vigorous activity were 9% less xx Preface Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203 Ask an Expert. These boxed features, written by Melina B. Jampolis, M.D., engage students by presenting questions and answers about nutrition and health, as related to chemistry, that are relevant and important in today’s world. Examples. To reinforce students in their problem-solving skill development, complete step-by-step solutions for numerous examples are included. Learning Checks. Short self-check exercises follow examples and discussions of key or difficult concepts. A complete set of solutions is included in Appendix C. These allow students to measure immediately their understanding and progress. Study Skills. Most chapters contain a Study Skills feature in which a challenging topic, skill, or concept of the chapter is addressed. Study suggestions, analogies, and approaches are provided to help students master these ideas. STUdy SKILLS 14.1 A Reaction Map for Aldehydes and Ketones This reaction map is designed to help you master organic is to react with the functional group. If the reacting func- reactions. Whenever you are trying to complete an organic tional group is an aldehyde or a ketone, find the reagent in reaction, use these two basic steps: (1) Identify the func- the summary diagram, and use the diagram to predict the tional group that is to react, and (2) Identify the reagent that correct products. Aldehyde or Ketone (O) H2, Pt alcohol Oxidation Hydrogenation Hemi formation If If If If If If aldehyde ketone aldehyde ketone aldehyde ketone Carboxylic No Primary Secondary Hemiacetal Hemiketal acid reaction alcohol alcohol alcohol Acetal Ketal how Reactions Occur. The mechanisms of representative organic reactions are presented in four boxed inserts to help students dispel the mystery of how these reactions take place. Concept Summary. Located at the end of each chapter, this feature provides a con- cise review of the concepts and includes suggested exercises to check achievement of the learning objectives related to the concepts. Concept Summary Symbols and Formulas Symbols based on names have are located in the nuclei of atoms. Negatively charged elec- been assigned to every element. Most consist of a single capi- trons with a mass of 1/1836 u are located outside the nuclei tal letter followed by a lowercase letter. A few consist of a of atoms. single capital letter. Compounds are represented by form