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  • 1. Rest in Peace to Aaron Swartz beloved friend of theinternet, defender for freedom of speech and information,May your struggle not be in vain, the earth is 4.5 billionyears, mankind has been around 160,000 yrs and theaverage span of an individual is just 70, but the idea offree universal knowledge can never die.

2. Periodic Table of ElementsRepresentative elementsHe4.0035 6 7 8 9 10B C N O F Ne10.81 12.01 14.01 16.00 19.00 20.1813 14 15 16 17 18Al Si P S Cl Ar26.98 28.09 30.97 32.07 35.45 39.95Ga Ge As Se Br KrRb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I XeCs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn114Fr Ra Ac Rf Db Sg Bh Hs MtHLi BeTransition elementsNa MgK Ca Sc Ti V Cr Mn Fe Co Ni Cu ZnActinides1Group1A2Group2A33B44B55B66B77B8 98B10 111B122B*Lanthanides111 11213 411 12219 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 3637 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 5455 56 57* 72 73 74 75 76 77 78 79 80 81 82 83 84 85 8687 88 89 104 105 106 107 108 109 110Ds Rg(272)11358 59 60 61 62 63 64 65 66 67 68 69 70 71Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu90 91 92 93 94 95 96 97 98 99 100 101 102 103Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr1.0086.941 9.01222.99 24.3139.10 40.08 44.96 47.87 50.94 52.00 54.94 55.85 58.93 58.69 63.55 65.41 69.72 72.64 74.92 78.96 79.90 83.8085.47 87.62 88.91 91.22 92.91 95.94 (99) 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3132.9 137.3 138.9 178.5 180.9 183.8 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 (209) (210) (222)(223) (226) (227) (261) (262) (266) (264) (265) (266) (271)140.1 140.9 144.2 (145) 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.0 175.0232.0 231.0 238.0 (237) (244) (243) (247) (247) (251) (252) (257) (258) (259) (262)Periodnumber123456713Group3A14Group4A15Group5A16Group6A17Group7A18Group8AAlkalimetalsNoblegasesAlkalineearthmetalsHalogensMetals Metalloids Nonmetals115(285) (284) (289) (288)116118(292) (294)Cn 3. ATOMIC MASSES OF THE ELEMENTSName Symbol Atomic Number Atomic MassaActinium Ac 89 (227)bAluminum Al 13 26.98Americium Am 95 (243)Antimony Sb 51 121.8Argon Ar 18 39.95Arsenic As 33 74.92Astatine At 85 (210)Barium Ba 56 137.3Berkelium Bk 97 (247)Beryllium Be 4 9.012Bismuth Bi 83 209.0Bohrium Bh 107 (264)Boron B 5 10.81Bromine Br 35 79.90Cadmium Cd 48 112.4Calcium Ca 20 40.08Californium Cf 98 (251)Carbon C 6 12.01Cerium Ce 58 140.1Cesium Cs 55 132.9Chlorine Cl 17 35.45Chromium Cr 24 52.00Cobalt Co 27 58.93Copernicium Cn 112 (285)Copper Cu 29 63.55Curium Cm 96 (247)Darmstadtium Ds 110 (271)Dubnium Db 105 (262)Dysprosium Dy 66 162.5Einsteinium Es 99 (252)Erbium Er 68 167.3Europium Eu 63 152.0Fermium Fm 100 (257)Fluorine F 9 19.00Francium Fr 87 (223)Gadolinium Gd 64 157.3Gallium Ga 31 69.72Germanium Ge 32 72.64Gold Au 79 197.0Hafnium Hf 72 178.5Hassium Hs 108 (265)Helium He 2 4.003Holmium Ho 67 164.9Hydrogen H 1 1.008Indium In 49 114.8Iodine I 53 126.9Iridium Ir 77 192.2Iron Fe 26 55.85Krypton Kr 36 83.80Lanthanum La 57 138.9Lawrencium Lr 103 (262)Lead Pb 82 207.2Lithium Li 3 6.941Lutetium Lu 71 175.0Magnesium Mg 12 24.31Manganese Mn 25 54.94Meitnerium Mt 109 (268)Mendelevium Md 101 (258)Mercury Hg 80 200.6Name Symbol Atomic Number Atomic MassaMolybdenum Mo 42 95.94Neodymium Nd 60 144.2Neon Ne 10 20.18Neptunium Np 93 (237)Nickel Ni 28 58.69Niobium Nb 41 92.91Nitrogen N 7 14.01Nobelium No 102 (259)Osmium Os 76 190.2Oxygen O 8 16.00Palladium Pd 46 106.4Phosphorus P 15 30.97Platinum Pt 78 195.1Plutonium Pu 94 (244)Polonium Po 84 (209)Potassium K 19 39.10Praseodymium Pr 59 140.9Promethium Pm 61 (145)Protactinium Pa 91 231.0Radium Ra 88 (226)Radon Rn 86 (222)Rhenium Re 75 186.2Rhodium Rh 45 102.9Roentgenium Rg 111 (272)Rubidium Rb 37 85.47Ruthenium Ru 44 101.1Rutherfordium Rf 104 (261)Samarium Sm 62 150.4Scandium Sc 21 44.96Seaborgium Sg 106 (266)Selenium Se 34 78.96Silicon Si 14 28.09Silver Ag 47 107.9Sodium Na 11 22.99Strontium Sr 38 87.62Sulfur S 16 32.07Tantalum Ta 73 180.9Technetium Tc 43 (99)Tellurium Te 52 127.6Terbium Tb 65 158.9Thallium Tl 81 204.4Thorium Th 90 232.0Thulium Tm 69 168.9Tin Sn 50 118.7Titanium Ti 22 47.87Tungsten W 74 183.8Uranium U 92 238.0Vanadium V 23 50.94Xenon Xe 54 131.3Ytterbium Yb 70 173.0Yttrium Y 39 88.91Zinc Zn 30 65.41Zirconium Zr 40 91.22 113 (284) 114 (289) 115 (288) 116 (292) 118 (294)aValues for atomic masses are given to four significant figures.bValues in parentheses are the mass number of an important radioactive isotope. 4. CHEMISTRY 5. K A R E N C. T I M B E R L A K ECHEMISTRYAn Introduction to General, Organic,and Biological ChemistryELEVENTH EDITION 6. Editor in Chief: Adam JaworskiMarketing Manager: Erin GardnerAssociate Editor: Jessica NeumannEditorial Assistant: Lisa TarabokjiaMarketing Assistant: Nicola HoustonManaging Editor, Chemistry and Geosciences: Gina M. CheselkaSenior Project Manager, Production: Beth SweetenSenior Media Producer: Angela BernhardtMastering Media Producer: Kate BraytonSenior Media Production Supervisor: Liz WinerMedia Editor: David ChavezSenior Technical Art Specialist: Connie LongArt Studio: Precision GraphicsArt Director: Derek BacchusInterior and Cover Design: Tamara NewnamSenior Manufacturing and Operations Manager: Nick SklitsisOperations Specialist: Maura ZaldivarImage Permissions Coordinator: Elaine SoaresPhoto Researcher: Eric ShraderProduction Supervision/Composition: Prepare, Inc.Cover Photograph: David Alayeto/Getty ImagesCredits and acknowledgments borrowed from other sources and reproduced, with permission, in thistextbook appear on p. C-1.Copyright 2012, 2009, 2006, 2003, 1999, 1996, 1992, 1988, 1983, 1979, 1976 Pearson Education, Inc.,publishing as Prentice Hall. All rights reserved. Manufactured in the United States of America. Thispublication is protected by Copyright and permission should be obtained from the publisher prior to anyprohibited reproduction, storage in a retrieval system, or transmission in any form or by any means,electronic, mechanical, photocopying, recording, or likewise. To obtain permission(s) to use material fromthis work, please submit a written request to Pearson Education, Inc., Permissions Department,1900 E. Lake Ave., Glenview, IL 60025.Many of the designations used by manufacturers and sellers to distinguish their products are claimed astrademarks. Where those designations appear in this book, and the publisher was aware of a trademarkclaim, the designations have been printed in initial caps or all caps.Prentice Hall is a trademark, in the U.S. and/or other countries, of Pearson Education, Inc. or its afffiliates.Library of Congress Cataloging-in-Publication DataTimberlake, Karen C.Chemistry : an introduction to general, organic, and biological chemistry /Karen C. Timberlake.11th ed.p. cm.Includes bibliographical references and index.ISBN 978-0-321-69345-7 (alk. paper)1. ChemistryTextbooks. I. Title.QD31.3.T55 2012540dc222010029053ISBN-10: 0-321-69345-0ISBN-13: 978-0-321-69345-7Printed in the United States10 9 8 7 6 5 4 3 2 1www.pearsonhighered.com 7. 1 Chemistry and Measurements 12 Matter and Energy 453 Atoms and Elements 854 Compounds and Their Bonds 1255 Chemical Quantities and Reactions 1676 Gases 2137 Solutions 2458 Acids and Bases 2859 Nuclear Radiation 31910 Introduction to Organic Chemistry: Alkanes 35311 Unsaturated Hydrocarbons 38512 Organic Compounds with Oxygen and Sulfur 41013 Carbohydrates 45214 Carboxylic Acids, Esters, Amines, and Amides 48115 Lipids 51716 Amino Acids, Proteins, and Enzymes 55717 Nucleic Acids and Protein Synthesis 60018 Metabolic Pathways and Energy Production 633vBRIEF CONTENTS 8. vi1Chemistry andMeasurements 11.1 Chemistry and Chemicals 3Chemistry Link to History Early Chemists:The Alchemists 31.2 A Study Plan for Learning Chemistry 51.3 Units of Measurement 8Explore Your World Units Listed on Labels 101.4 Scientific Notation 111.5 Measured Numbers and Significant Figures 141.6 Significant Figures in Calculations 171.7 Prefixes and Equalities 211.8 Writing Conversion Factors 25Explore Your World SI and Metric Equalitieson Product Labels 27Chemistry Link to Health Toxicology andRisk-Benefit Assessment 281.9 Problem Solving 29Career Focus Veterinary Technician (VT) 311.10 Density 33Explore Your World Sink or Float? 33Chemistry Link to Health Bone Density 35Concept Map 38Chapter Review 39Key Terms 40Understanding the Concepts 40Additional Questions and Problems 42Challenge Questions 42Answers 432Matter andEnergy 452.1 Classification of Matter 46Chemistry Link to Health Breathing Mixturesfor Scuba 492.2 States and Properties of Matter 502.3 Energy 54Chemistry Link to the Environment Carbon Dioxideand Global Warming 562.4 Temperature 57Career Focus Surgical Technologist 59Chemistry Link to Health Variation in BodyTemperature 612.5 Specific Heat 612.6 Energy and Nutrition 64Explore Your World Counting Calories 65Chemistry Link to Health Losing and Gaining Weight 662.7 Changes of State 67Career Focus Histologist 69Chemistry Link to Health Steam Burns 71Concept Map 75Chapter Review 76Key Terms 76Understanding the Concepts 77Additional Questions and Problems 79Challenge Questions 80Answers 81Combining Ideas from Chapters 1 and 2 833Atoms andElements 853.1 Elements and Symbols 86Chemistry Link to Health Toxicity of Mercury 88Chemistry Link to Industry Many Forms of Carbon 893.2 The Periodic Table 89Chemistry Link to Health Elements Essentialto Health 92Career Focus Materials Scientist 953.3 The Atom 96Explore Your World Repulsion and Attraction 993.4 Atomic Number and Mass Number 99Career Focus Optician 1013.5 Isotopes and Atomic Mass 1023.6 Electron Energy Levels 106Chemistry Link to the Environment Energy-SavingFluorescent Bulbs 107CONTENTS 9. CONTENTS viiChemistry Link to Health Biological Reactionsto UV Light 1113.7 Trends in Periodic Properties 111Concept Map 118Chapter Review 119Key Terms 120Understanding the Concepts 120Additional Questions and Problems 121Challenge Questions 122Answers 1234Compounds andTheir Bonds 1254.1 Octet Rule and Ions 126Chemistry Link to Industry Some Uses forNoble Gases 127Chemistry Link to Health Some Important Ionsin the Body 1304.2 Ionic Compounds 131Career Focus Physical Therapist 1324.3 Naming and Writing Ionic Formulas 1344.4 Polyatomic Ions 1374.5 Covalent Compounds and Their Names 1414.6 Electronegativity and Bond Polarity 1494.7 Shapes and Polarity of Molecules 1524.8 Attractive Forces in Compounds 158Concept Map 160Chapter Review 161Key Terms 162Understanding the Concepts 162Additional Questions and Problems 163Challenge Questions 164Answers 1655ChemicalQuantitiesand Reactions 1675.1 The Mole 1685.2 Molar Mass 172Explore Your World Calculating Molesin the Kitchen 1745.3 Chemical Reactions and Equations 1775.4 Types of Reactions 183Chemistry Link to Health Smog and Health Concerns 1885.5 OxidationReduction Reactions 189Explore Your World Oxidation of Fruitsand Vegetables 191Chemistry Link to the Environment Fuel Cells: CleanEnergy for the Future 1935.6 Mole Relationships in Chemical Equations 1935.7 Mass Calculations for Reactions 1975.8 Energy in Chemical Reactions 199Chemistry Link to Health Hot Packs and Cold Packs 200Concept Map 203Chapter Review 203Key Terms 204Understanding the Concepts 205Additional Questions and Problems 206Challenge Questions 208Answers 209Combining Ideas from Chapters 3 to 5 2116Gases 2136.1 Properties of Gases 214Explore Your World Forming a Gas 2176.2 Gas Pressure 217Chemistry Link to Health Measuring Blood Pressure 2196.3 Pressure and Volume (Boyles Law) 220Chemistry Link to Health PressureVolume Relationshipin Breathing 2236.4 Temperature and Volume (Charless Law) 224Chemistry Link to the Environment GreenhouseGases 2276.5 Temperature and Pressure (Gay-Lussacs Law) 228Career Focus Nurse Anesthetist 2296.6 The Combined Gas Law 2316.7 Volume and Moles (Avogadros Law) 2336.8 Partial Pressures (Daltons Law) 236Chemistry Link to Health Blood Gases 238Chemistry Link to Health Hyperbaric Chambers 239Concept Map 240Chapter Review 241Key Terms 241Understanding the Concepts 242Additional Questions and Problems 243Challenge Questions 243Answers 244 10. viii CONTENTS7Solutions 2457.1 Solutions 246Chemistry Link to Health Water in the Body 248Explore Your World Like Dissolves Like 2507.2 Electrolytes and Nonelectrolytes 250Career Focus Orthopedic Physician Assistant 252Chemistry Link to Health Electrolytesin Body Fluids 2547.3 Solubility 254Chemistry Link to Health Gout and Kidney Stones:A Problem of Saturation in Body Fluids 256Explore Your World Preparing Solutions 2577.4 Concentration of a Solution 2607.5 Dilution of Solutions 2667.6 Properties of Solutions 269Chemistry Link to Health Colloids and Solutionsin the Body 270Explore Your World Everyday Osmosis 273Chemistry Link to Health Dialysis by the Kidneysand the Artificial Kidney 276Concept Map 278Chapter Review 278Key Terms 279Understanding the Concepts 280Additional Questions and Problems 281Challenge Questions 282Answers 2828Acidsand Bases 2858.1 Acids and Bases 2868.2 Strengths of Acids and Bases 2918.3 Ionization of Water 2948.4 The pH Scale 297Chemistry Link to Health Stomach Acid, HCl 300Chemistry Link to the Environment Acid Rain 303Explore Your World Using Vegetables andFlowers as pH Indicators 3048.5 Reactions of Acids and Bases 304Chemistry Link to Health Antacids 3078.6 Buffers 308Chemistry Link to Health Buffers in the Blood 310Concept Map 311Chapter Review 312Key Terms 312Understanding the Concepts 313Additional Questions and Problems 314Challenge Questions 314Answers 315Combining Ideas from Chapters 6 to 8 3179NuclearRadiation 3199.1 Natural Radioactivity 320Chemistry Link to Health Biological Effectsof Radiation 3229.2 Nuclear Equations 324Chemistry Link to the Environment Radon inOur Homes 326Chemistry Link to Health Beta Emitters inMedicine 3289.3 Radiation Measurement 331Chemistry Link to Health Radiation and Food 3339.4 Half-Life of a Radioisotope 335Explore Your World Modeling Half-Lives 335Chemistry Link to the Environment Dating AncientObjects 3389.5 Medical Applications Using Radioactivity 338Chemistry Link to Health Other ImagingMethods 340Chemistry Link to Health Brachytherapy 342Chemistry Link to Health Radiation Doses in Diagnosticand Therapeutic Procedures 3429.6 Nuclear Fission and Fusion 343Chemistry Link to the Environment NuclearPower Plants 345Concept Map 346Chapter Review 347Key Terms 347Understanding the Concepts 348Additional Questions and Problems 349Challenge Questions 350Answers 350 11. CONTENTS ix10Introduction toOrganic Chemistry:Alkanes 35310.1 Organic Compounds 35410.2 Alkanes 357Career Focus Geologist 36010.3 Alkanes with Substituents 362Chemistry Link to Health Common Uses ofHalogenated Alkanes 36710.4 Properties of Alkanes 368Chemistry Link to Health Toxicity ofCarbon Monoxide 369Chemistry Link to Industry Crude Oil 37010.5 Functional Groups 371Chemistry Link to the Environment FunctionalGroups in Familiar Compounds 376Concept Map 377Chapter Review 378Summary of Naming 378Summary of Reactions 379Key Terms 379Understanding the Concepts 379Additional Questions and Problems 380Challenge Questions 382Answers 38311UnsaturatedHydrocarbons 38511.1 Alkenes and Alkynes 386Explore Your World Ripening Fruit 387Chemistry Link to the Environment Fragrant Alkenes 38911.2 CisTrans Isomers 390Explore Your World Modeling CisTrans Isomers 392Chemistry Link to the Environment Pheromones in InsectCommunication 394Chemistry Link to Health CisTrans Isomersfor Night Vision 39411.3 Addition Reactions 395Explore Your World Unsaturation in Fats and Oils 395Chemistry Link to Health Hydrogenation ofUnsaturated Fats 39611.4 Polymers of Alkenes 399Explore Your World Polymers and Recycling Plastics 39911.5 Aromatic Compounds 401Chemistry Link to Health Some CommonAromatic Compounds 403Chemistry Link to Health Polycyclic AromaticHydrocarbons (PAHs) 403Concept Map 404Chapter Review 404Summary of Naming 405Summary of Reactions 405Key Terms 405Understanding the Concepts 406Additional Questions and Problems 406Challenge Questions 408Answers 40812Organic Compoundswith Oxygenand Sulfur 41012.1 Alcohols, Phenols, Thiols, and Ethers 411Explore Your World Alcohols in Household Products 413Chemistry Link to Health Some ImportantAlcohols and Phenols 413Chemistry Link to Health Ethers as Anesthetics 41612.2 Properties of Alcohols and Ethers 417Chemistry Link to Health Hand Sanitizers and Ethanol 41912.3 Reactions of Alcohols and Thiols 420Chemistry Link to Health Methanol Poisoning 422Career Focus Pharmacist 423Chemistry Link to Health Oxidation of Alcoholin the Body 42312.4 Aldehydes and Ketones 425Chemistry Link to the Environment Vanilla 427Chemistry Link to Health Some ImportantAldehydes and Ketones 42912.5 Properties of Aldehydes and Ketones 43012.6 Chiral Molecules 434Explore Your World Using Gumdrops andToothpicks to Model Chiral Objects 436Chemistry Link to Health Enantiomers inBiological Systems 440Concept Map 441Chapter Review 441Summary of Naming 442Summary of Reactions 443Key Terms 443Understanding the Concepts 444Additional Questions and Problems 445Challenge Questions 447Answers 447Combining Ideas from Chapters 9 to 12 450 12. x CONTENTS13Carbohydrates 45213.1 Carbohydrates 45313.2 Fischer Projections of Monosaccharides 456Chemistry Link to Health Hyperglycemia andHypoglycemia 45813.3 Haworth Structures of Monosaccharides 45913.4 Chemical Properties of Monosaccharides 463Chemistry Link to Health Testing for Glucose in Urine 46413.5 Disaccharides 465Explore Your World Sugar and Sweeteners 466Career Focus Phlebotomist 467Chemistry Link to Health How Sweet IsMy Sweetener? 469Chemistry Link to Health Blood Types andCarbohydrates 47013.6 Polysaccharides 471Explore Your World Polysaccharides 473Concept Map 474Chapter Review 474Summary of Carbohydrates 475Summary of Reactions 475Key Terms 476Understanding the Concepts 476Additional Questions and Problems 477Challenge Questions 478Answers 47814Carboxylic Acids,Esters, Amines,and Amides 48114.1 Carboxylic Acids 482Chemistry Link to Health Alpha HydroxyAcids (AHAs) 48514.2 Properties of Carboxylic Acids 48614.3 Esters 488Chemistry Link to Health Salicylic Acid and Aspirin 490Chemistry Link to the Environment Plastics 491Chemistry Link to the Environment Cleaning Actionof Soaps 49414.4 Amines 495Chemistry Link to Health Amines in Health andMedicine 497Chemistry Link to Health Synthesizing Drugs 50214.5 Amides 503Career Focus Clinical Laboratory Technologist 504Chemistry Link to Health Amides in Health andMedicine 506Concept Map 508Chapter Review 508Summary of Naming 509Summary of Reactions 509Key Terms 511Understanding the Concepts 511Additional Questions and Problems 512Challenge Questions 513Answers 51415Lipids 51715.1 Lipids 518Explore Your World Solubility of Fats and Oils 51915.2 Fatty Acids 520Chemistry Link to Health Omega-3 Fatty Acidsin Fish Oils 52415.3 Waxes, Fats, and Oils 52515.4 Chemical Properties of Triacylglycerols 529Chemistry Link to Health Olestra: A Fat Substitute 530Chemistry Link to Health Trans Fatty Acidsand Hydrogenation 531Explore Your World Types of Fats 533Chemistry Link to the Environment Biodieselas an Alternative Fuel 53315.5 Glycerophospholipids 535Career Focus Physical Therapist 53715.6 Steroids: Cholesterol, Bile Salts,and Steroid Hormones 538Chemistry Link to Health Anabolic Steroids 54315.7 Cell Membranes 544Concept Map 547Chapter Review 548Summary of Reactions 548Key Terms 549Understanding the Concepts 549Additional Questions and Problems 550Challenge Questions 551Answers 551Combining Ideas from Chapters 13 to 15 555 13. CONTENTS xi16Amino Acids,Proteins,and Enzymes 55716.1 Proteins and Amino Acids 558Chemistry Link to Health Essential Amino Acids 56316.2 Amino Acids as Acids and Bases 563Career Focus Rehabilitation Specialist 56416.3 Formation of Peptides 56616.4 Levels of Protein Structure 568Chemistry Link to Health Polypeptides in the Body 568Chemistry Link to Health Protein Structure and Mad CowDisease 576Explore Your World Denaturation of Milk Protein 577Chemistry Link to Health Sickle-Cell Anemia 57816.5 Enzymes 57916.6 Enzyme Action 580Chemistry Link to Health Isoenzymes as DiagnosticTools 58316.7 Factors Affecting Enzyme Activity 584Explore Your World Enzyme Activity 58516.8 Enzyme Cofactors 589Concept Map 592Chapter Review 592Key Terms 593Understanding the Concepts 594Additional Questions and Problems 596Challenge Questions 597Answers 59717Nucleic Acidsand ProteinSynthesis 60017.1 Components of Nucleic Acids 601Career Focus Occupational Therapist 60417.2 Primary Structure of Nucleic Acids 60517.3 DNA Double Helix 607Chemistry Link to Health DNA Fingerprinting 61117.4 RNA and the Genetic Code 61117.5 Protein Synthesis 616Chemistry Link to Health Many Antibiotics InhibitProtein Synthesis 61917.6 Genetic Mutations 619Explore Your World A Model for DNA Replicationand Mutation 62117.7 Viruses 623Chemistry Link to Health Cancer 626Concept Map 627Chapter Review 628Key Terms 628Understanding the Concepts 629Additional Questions and Problems 629Challenge Questions 630Answers 63018Metabolic Pathwaysand EnergyProduction 63318.1 Metabolism and ATP Energy 634Chemistry Link to Health ATP Energy and Ca2 Neededto Contract Muscles 63818.2 Digestion of Foods 639Explore Your World Carbohydrate Digestion 639Chemistry Link to Health Lactose Intolerance 64018.3 Coenzymes in Metabolic Pathways 64218.4 Glycolysis: Oxidation of Glucose 64618.5 The Citric Acid Cycle 65218.6 Electron Transport and Oxidative Phosphorylation 656Chemistry Link to Health Toxins: Inhibitors of ElectronTransport 658Chemistry Link to Health ATP Synthase and Heatingthe Body 66018.7 Oxidation of Fatty Acids 663Explore Your World Fat Storage and Blubber 665Chemistry Link to Health Stored Fat and Obesity 666Chemistry Link to Health Ketone Bodies and Diabetes 66918.8 Degradation of Amino Acids 669Concept Map 674Chapter Review 675Summary of Key Reactions 676Key Terms 678Understanding the Concepts 678Additional Questions and Problems 679Challenge Questions 679Answers 680Combining Ideas from Chapters 16 to 18 682Credits C-1Glossary/Index I-1 14. APPLICATIONS AND ACTIVITIESxiiExplore Your WorldUnits Listed on Labels 10SI and Metric Equalities on Product Labels 27Sink or Float? 33Counting Calories 65Repulsion and Attraction 99Calculating Moles in the Kitchen 174Oxidation of Fruits and Vegetables 191Forming a Gas 217Like Dissolves Like 250Preparing Solutions 257Everyday Osmosis 273Using Vegetables and Flowers as pH Indicators 304Modeling Half-Lives 335Ripening Fruit 387Modeling CisTrans Isomers 392Unsaturation in Fats and Oils 395Polymers and Recycling Plastics 399Alcohols in Household Products 413Using Gumdrops and Toothpicks to Model Chiral Objects 436Sugar and Sweeteners 466Polysaccharides 473Solubility of Fats and Oils 519Types of Fats 533Denaturation of Milk Protein 577Enzyme Activity 585A Model for DNA Replication and Mutation 621Carbohydrate Digestion 639Fat Storage and Blubber 665Chemistry Link to HealthToxicology and Risk-Benefit Assessment 28Bone Density 35Breathing Mixtures for Scuba 49Variation in Body Temperature 61Losing and Gaining Weight 66Steam Burns 71Toxicity of Mercury 88Elements Essential to Health 92Biological Reactions to UV Light 111Some Important Ions in the Body 130Smog and Health Concerns 188Hot Packs and Cold Packs 200Measuring Blood Pressure 219PressureVolume Relationship in Breathing 223Blood Gases 238Hyperbaric Chambers 239Water in the Body 248Electrolytes in Body Fluids 254Gout and Kidney Stones: A Problem of Saturationin Body Fluids 256Colloids and Solutions in the Body 270Dialysis by the Kidneys and the Artificial Kidney 276Stomach Acid, HCl 300Antacids 307Buffers in the Blood 310Biological Effects of Radiation 322Beta Emitters in Medicine 328Radiation and Food 333Other Imaging Methods 340Brachytherapy 342Radiation Doses in Diagnostic and Therapeutic Procedures 342Common Uses of Halogenated Alkanes 367Toxicity of Carbon Monoxide 369CisTrans Isomers for Night Vision 394Hydrogenation of Unsaturated Fats 396Some Common Aromatic Compounds 403Polycyclic Aromatic Hydrocarbons (PAHs) 403Some Important Alcohols and Phenols 413Ethers as Anesthetics 416Hand Sanitizers and Ethanol 419Methanol Poisoning 422Oxidation of Alcohol in the Body 423Some Important Aldehydes and Ketones 429Enantiomers in Biological Systems 440Hyperglycemia and Hypoglycemia 458Testing for Glucose in Urine 464How Sweet Is My Sweetener? 469Blood Types and Carbohydrates 470Alpha Hydroxy Acids (AHAs) 485Salicylic Acid and Aspirin 490Amines in Health and Medicine 497Synthesizing Drugs 502Amides in Health and Medicine 506Omega-3 Fatty Acids in Fish Oils 524Olestra: A Fat Substitute 530Trans Fatty Acids and Hydrogenation 531Anabolic Steroids 543Essential Amino Acids 563Polypeptides in the Body 568Protein Structure and Mad Cow Disease 576Sickle-Cell Anemia 578Isoenzymes as Diagnostic Tools 583DNA Fingerprinting 611Many Antibiotics Inhibit Protein Synthesis 619Cancer 626ATP Energy and Ca2 Needed to Contract Muscles 638Lactose Intolerance 640Toxins: Inhibitors of Electron Transport 658ATP Synthase and Heating the Body 660Stored Fat and Obesity 666Ketone Bodies and Diabetes 669 15. APPLICATIONS AND ACTIVITIES xiiiCareer FocusVeterinary Technician (VT) 31Surgical Technologist 59Histologist 69Materials Scientist 95Optician 101Physical Therapist 132Nurse Anesthetist 229Orthopedic Physician Assistant 252Geologist 360Pharmacist 423Phlebotomist 467Clinical Laboratory Technologist 504Physical Therapist 537Rehabilitation Specialist 564Occupational Therapist 604Chemistry Link to theEnvironmentCarbon Dioxide and Global Warming 56Energy-Saving Fluorescent Bulbs 107Fuel Cells: Clean Energy for the Future 193Greenhouse Gases 227Acid Rain 303Radon in Our Homes 326Dating Ancient Objects 338Nuclear Power Plants 345Functional Groups in Familiar Compounds 376Fragrant Alkenes 389Pheromones in Insect Communication 394Vanilla 427Plastics 491Cleaning Action of Soaps 494Biodiesel as an Alternative Fuel 533Chemistry Link to IndustryMany Forms of Carbon 89Some Uses for Noble Gases 127Crude Oil 370Chemistry Link to HistoryEarly Chemists: The Alchemists 3Guide to Problem SolvingGuide to Problem Solving Using Conversion Factors 29Guide to Calculating Density 34Guide to Using Density 36Guide to Calculations Using Specific Heat 63Guide to Calculations Using Heat of Fusion 68Guide to Calculations Using Heat of Vaporization 70Guide to Naming Ionic Compounds with MetalsThat Form a Single Ion 134Guide to Naming Ionic Compounds with VariableCharge Metals 136Guide to Writing Formulas from the Name of an IonicCompound 136Guide to Naming Ionic Compounds with Polyatomic Ions 140Guide to Drawing Electron-Dot Formulas 144Guide to Naming Covalent Compounds 146Guide to Writing Formulas for Covalent Compounds 147Guide to Predicting Molecular Shape (VSEPR Theory) 156Guide to Calculating the Atoms or Moleculesof a Substance 170Guide to Calculating the Moles of an Elementin a Compound 172Guide to Calculating Molar Mass 173Guide to Calculating the Moles (or Grams) of aSubstance from Grams (or Moles) 175Guide to Balancing a Chemical Equation 180Guide to Using MoleMole Factors 196Guide to Calculating the Masses of Reactants andProducts in a Chemical Reaction 197Guide to Using the Gas Laws 221Guide to Using Molar Volume 235Guide to Solving for Partial Pressure 238Guide to Calculating Solution Concentration 261Guide to Using Concentration to Calculate Mass or Volume 264Guide to Calculating Dilution Quantities 267Guide to Calculating [H3O] and [OH] inAqueous Solutions 296Guide to Calculating pH of an Aqueous Solution 299Guide to Balancing an Equation for Neutralization 305Guide to Calculations for an AcidBase Titration 307Guide to Completing a Nuclear Equation 326Guide to Using Half-Lives 336Guide to Naming Alkanes 364Guide to Drawing Alkane Formulas 366Guide to Naming Alkenes and Alkynes 388Guide to Naming Alcohols 412Guide to Naming Aldehydes 426Guide to Naming Ketones 428Guide to Drawing Haworth Structures 462Guide to Naming Carboxylic Acids 484Guide to Naming Esters 491 16. Karen and Bill Timberlake at the Natural History Museum where they aresupporters of childrens environmental programs.KAREN TIMBERLAKEAbout the Authoris Professor Emerita of Chemistry at LosAngeles Valley College, where she taughtchemistry for allied health andpreparatory chemistry for 36 years. She receivedher bachelors degree in chemistry from the Universityof Washington and her masters degree in biochemistryfrom the University of California at Los Angeles.Professor Timberlake has been writingchemistry textbooks for 34 years. During thattime, her name has become associated withthe strategic use of pedagogical tools thatpromote student success in chemistry andthe application of chemistry to real-lifesituations. More than one million students havelearned chemistry using texts, laboratory manuals, andstudy guides written by Karen Timberlake. In additionto Chemistry: An Introduction to General, Organic, andBiological Chemistry, Eleventh Edition, she is also theauthor of General, Organic, and Biological Chemistry,Structures of Life, Third Edition, and Basic Chemistry,Third Edition.Professor Timberlake belongs to numerousscientific and educational organizations includingthe American Chemical Society (ACS) and theNational Science Teachers Association (NSTA).She was the Western Regional Winner of Excellencein College Chemistry Teaching Award given bythe Chemical ManufacturersAssociation. She received theMcGuffey Award in PhysicalSciences from the TextbookAuthors Association for hertextbook Chemistry: An Introductionto General, Organic, and BiologicalChemistry, Eighth Edition. Shereceived the Texty TextbookExcellence Award from the TextbookAuthors Association for the firstedition of Basic Chemistry. She hasparticipated in education grants forscience teaching including the LosAngeles Collaborative for TeachingExcellence (LACTE) and a Title III grant at hercollege. She speaks at conferences and educationalmeetings on the use of student-centered teachingmethods in chemistry to promote the learningsuccess of students.Her husband, William Timberlake, who hascontributed to writing this text, is Professor Emeritusof Chemistry at Los Angeles Harbor College, wherehe taught preparatory and organic chemistry for 36years. He received his bachelors degree in chemistryfrom Carnegie Mellon University and his mastersdegree in organic chemistry from the University ofCalifornia at Los Angeles. When the ProfessorsTimberlake are not writing textbooks, they relax byhiking, traveling, trying new restaurants, cooking,playing tennis, and taking care of their grandchildren,Daniel and Emily.DEDICATIONI dedicate this book tos