General, organic, and biochemistry PDF
Preview General, organic, and biochemistry
This International Student Edition is for use outside of the U.S. G , O , eneral rGanic B and iOchemistry TENTH EDITION Katherine J. Denniston Joseph J. Topping Danaè R. Quirk Dorr Robert L. Caret General, Organic, and Biochemistry TENTH EDITION Katherine J. Denniston Towson University Joseph J. Topping Towson University Danaè R. Quirk Dorr Minnesota State University, Mankato Robert L. Caret University System of Maryland GENERAL, ORGANIC, AND BIOCHEMISTRY Published by McGraw-Hill Education, 2 Penn Plaza, New York, NY 10121. Copyright ©2020 by McGraw-Hill Education. All rights reserved. Printed in the United States of America. No part of this publication may be reproduced or distributed in any form or by any means, or stored in a database or retrieval system, without the prior written consent of McGraw-Hill Education, including, but not limited to, in any network or other electronic storage or transmission, or broadcast for distance learning. Some ancillaries, including electronic and print components, may not be available to customers outside the United States. This book is printed on acid-free paper. 1 2 3 4 5 6 7 8 9 LWI 21 20 19 ISBN 978-1-260-56588-1 MHID 1-260-56588-2 Cover Image: ©Tammy616/Getty Images All credits appearing on page or at the end of the book are considered to be an extension of the copyright page. The Internet addresses listed in the text were accurate at the time of publication. The inclusion of a website does not indicate an endorsement by the authors or McGraw-Hill Education, and McGraw-Hill Education does not guarantee the accuracy of the information presented at these sites. mheducation.com/highered Brief Contents GENERAL CHEMISTRY 1 Chemistry: Methods and Measurement . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 2 The Structure of the Atom and the Periodic Table . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44 3 Structure and Properties of Ionic and Covalent Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . 85 4 Calculations and the Chemical Equation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127 5 States of Matter: Gases, Liquids, and Solids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164 6 Solutions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 192 7 Energy, Rate, and Equilibrium . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 226 8 Acids and Bases and Oxidation-Reduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 262 9 The Nucleus, Radioactivity, and Nuclear Medicine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 299 ORGANIC CHEMISTRY 10 An Introduction to Organic Chemistry: The Saturated Hydrocarbons . . . . . . . . . . . . . . . . . 330 11 The Unsaturated Hydrocarbons: Alkenes, Alkynes, and Aromatics . . . . . . . . . . . . . . . . . . . . 369 12 Alcohols, Phenols, Thiols, and Ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 412 13 Aldehydes and Ketones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 448 14 Carboxylic Acids and Carboxylic Acid Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 478 15 Amines and Amides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 518 BIOCHEMISTRY 16 Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 556 17 Lipids and Their Functions in Biochemical Systems . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 592 18 Protein Structure and Function . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 627 19 Enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 657 20 Introduction to Molecular Genetics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 691 21 Carbohydrate Metabolism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 733 22 Aerobic Respiration and Energy Production . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 767 23 Fatty Acid Metabolism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 798 iii Contents Perspectives xii Chapter Map 37 Preface xiv Summary 38 Questions and Problems 39 Multiple Concept Problems 42 GENERAL CHEMISTRY 2 The Structure of the Atom and the Periodic Table 44 1 Chemistry: Methods and Measurement 1 2.1 Composition of the Atom 45 Electrons, Protons, and 1.1 Strategies for Success in Neutrons 45 Chemistry 2 Isotopes 47 ©antonyspencer/Getty Images The Science of Learning Chemistry 2 2.2 Development of Atomic Theory 49 Learning General Chemistry 2 ©1joe/Getty Images Dalton’s Theory 49 1.2 The Discovery Process 4 Evidence for Subatomic Particles: Electrons, Protons, Chemistry 4 and Neutrons 49 The Scientific Method 5 Chemistry at the Crime Scene: Microbial Forensics 50 Models in Chemistry 6 Evidence for the Nucleus 51 A Human Perspective: The Scientific Method 7 2.3 Light, Atomic Structure, and the Bohr Atom 52 1.3 The Classification of Matter 8 Electromagnetic Radiation 52 States of Matter 8 Photons 53 Composition of Matter 8 The Bohr Atom 53 Physical Properties and Physical Change 10 Green Chemistry: Practical Applications of Electromagnetic Chemical Properties and Chemical Change 11 Radiation 55 Intensive and Extensive Properties 12 Modern Atomic Theory 56 A Human Perspective: Atomic Spectra and the 1.4 The Units of Measurement 12 Fourth of July 57 Mass 13 Length 14 2.4 The Periodic Law and the Periodic Table 58 Volume 14 Numbering Groups in the Periodic Table 59 Time 15 Periods 60 Metals and Nonmetals 60 1.5 The Numbers of Measurement 15 A Medical Perspective: Copper Deficiency and Wilson’s Significant Figures 15 Disease 61 Recognition of Significant Figures 16 Information Contained in the Periodic Table 61 Scientific Notation 17 Accuracy and Precision 18 2.5 Electron Arrangement and the Periodic Table 62 Exact (Counted) and Inexact Numbers 19 The Quantum Mechanical Atom 62 Rounding Numbers 19 Principal Energy Levels, Sublevels, and Orbitals 63 Significant Figures in Calculation of Results 20 Electron Configurations 64 Guidelines for Writing Electron Configurations 1.6 Unit Conversion 22 of Atoms 65 Conversion of Units within the Same System 23 Electron Configurations and the Periodic Table 69 Factor-Label Method 23 Shorthand Electron Configurations 69 Conversion of Units Between Systems 25 A Medical Perspective: Curiosity and the Science 2.6 Valence Electrons and the Octet Rule 70 That Leads to Discovery 27 Valence Electrons 70 The Octet Rule 70 1.7 Additional Experimental Quantities 29 Temperature 29 Ions 71 Energy 30 Ion Formation and the Octet Rule 72 Concentration 31 A Medical Perspective: Dietary Calcium 75 Density and Specific Gravity 31 2.7 Trends in the Periodic Table 76 A Human Perspective: Food Calories 32 Atomic Size 76 A Medical Perspective: Assessing Obesity: Ion Size 76 The Body-Mass Index 35 Ionization Energy 77 A Human Perspective: Quick and Useful Analysis 36 Electron Affinity 78 Contents v Chapter Map 79 4.4 Balancing Chemical Equations 140 Summary 80 4.5 Precipitation Reactions 143 Questions and Problems 81 4.6 Net Ionic Equations 144 Multiple Concept Problems 84 Writing Net Ionic Equations 144 3 Structure and Properties of Ionic 4.7 Acid-Base Reactions 146 and Covalent Compounds 85 4.8 Oxidation-Reduction Reactions 146 3.1 Chemical Bonding 86 4.9 Calculations Using the Chemical Equation 146 Lewis Symbols 86 General Principles 146 Principal Types of Chemical Bonds: Using Conversion Factors 147 Ionic and Covalent 86 A Human Perspective: The Chemistry of Automobile Air Bags 151 Source: Centers for Disease Polar Covalent Bonding Control and Prevention (CDC) A Medical Perspective: Carbon Monoxide Poisoning: A Case of and Electronegativity 90 Combining Ratios 154 Theoretical and Percent Yield 155 3.2 Naming Compounds and Writing Formulas of Compounds 93 A Medical Perspective: Pharmaceutical Chemistry: The Practical Ionic Compounds 93 Significance of Percent Yield 156 Covalent Compounds 98 A Medical Perspective: Unwanted Crystal Formation 99 Chapter Map 158 Summary 159 3.3 Properties of Ionic and Covalent Compounds 101 Questions and Problems 160 Physical State 101 Multiple Concept Problems 163 Melting and Boiling Points 101 Structure of Compounds in the Solid State 101 5 States of Matter: Gases, A Medical Perspective: Rebuilding Our Teeth 102 Liquids, and Solids 164 Solutions of Ionic and Covalent Compounds 102 3.4 Drawing Lewis Structures of Molecules and Polyatomic Ions 102 5.1 The Gaseous State 165 Lewis Structures of Molecules 102 Ideal Gas Concept 165 A Medical Perspective: Blood Pressure and the Sodium Ion/ Measurement of Properties Potassium Ion Ratio 105 of Gases 166 ©Pixtal/AGE Fotostock Lewis Structures of Polyatomic Ions 105 Kinetic Molecular Theory of Gases 166 Lewis Structure, Stability, Multiple Bonds, and Bond Energies 109 A Human Perspective: The Demise of the Hindenburg 167 Isomers 110 Properties of Gases and the Kinetic Molecular Theory 167 Lewis Structures and Resonance 110 Boyle’s Law 168 Lewis Structures and Exceptions to the Octet Rule 112 Charles’s Law 169 Lewis Structures and Molecular Geometry; VSEPR Theory 113 Combined Gas Law 171 Periodic Molecular Geometry Relationships 116 Avogadro’s Law 173 Lewis Structures and Polarity 118 Molar Volume of a Gas 174 Gas Densities 174 3.5 Properties Based on Molecular Geometry and Intermolecular The Ideal Gas Law 175 Forces 120 Dalton’s Law of Partial Pressures 177 Solubility 120 Green Chemistry: The Greenhouse Effect and Global Climate Boiling Points of Liquids and Melting Points of Solids 120 Change 178 Chapter Map 122 Ideal Gases Versus Real Gases 178 Summary 123 5.2 The Liquid State 179 Questions and Problems 124 Compressibility 179 Multiple Concept Problems 126 Viscosity 179 4 Calculations and the Chemical Surface Tension 180 Vapor Pressure of a Liquid 180 Equation 127 Boiling Point and Vapor Pressure 181 4.1 The Mole Concept and Atoms 128 van der Waals Forces 181 The Mole and Avogadro’s Number 128 Hydrogen Bonding 182 Calculating Atoms, Moles, and Mass 130 Chemistry at the Crime Scene: Explosives at the Airport 183 4.2 The Chemical Formula, Formula 5.3 The Solid State 184 Mass, and Molar Mass 134 Properties of Solids 184 The Chemical Formula 134 ©Wilawan Khasawong/Alamy Types of Crystalline Solids 185 Stock Photo Formula Mass and Molar Mass 134 Sublimation of Solids 185 A Human Perspective: Gemstones 186 4.3 The Chemical Equation and the Information It Conveys 136 A Recipe for Chemical Change 136 Chapter Map 187 Features of a Chemical Equation 137 Summary 188 The Experimental Basis of a Chemical Equation 137 Questions and Problems 188 Strategies for Writing Chemical Equations 138 Multiple Concept Problems 191 vi Contents 6 Solutions 192 7.4 Equilibrium 245 Physical Equilibrium 245 6.1 Properties of Solutions 193 Chemical Equilibrium 246 General Properties of Liquid The Generalized Equilibrium Constant Expression for a Solutions 193 Chemical Reaction 247 True Solutions, Colloidal Dispersions, Writing Equilibrium Constant Expressions 247 and Suspensions 194 ©Juice Images/Alamy Stock Interpreting Equilibrium Constants 248 Photo Degree of Solubility 195 Calculating Equilibrium Constants 250 Solubility and Equilibrium 196 Using Equilibrium Constants 251 Solubility of Gases: Henry’s Law 196 LeChatelier’s Principle 252 A Human Perspective: Scuba Diving: Nitrogen and the Bends 197 A Human Perspective: An Extraordinary Molecule 255 Henry’s Law and Respiration 197 Chapter Map 256 A Medical Perspective: Blood Gases and Respiration 198 Summary 256 6.2 Concentration Based on Mass 198 Questions and Problems 257 Mass/Volume Percent 198 Multiple Concept Problems 260 Mass/Mass Percent 200 Parts per Thousand (ppt) and Parts per Million (ppm) 201 8 Acids and Bases and Oxidation-Reduction 262 6.3 Concentration Based on Moles 202 Molarity 202 8.1 Acids and Bases 263 Dilution 204 Acid and Base Theories 263 6.4 Concentration-Dependent Solution Properties 206 Amphiprotic Nature of Water 265 Vapor Pressure Lowering 207 Conjugate Acid-Base Pairs 265 Freezing Point Depression and Boiling Point Elevation 207 Acid and Base Strength 266 Calculating Freezing Points and Boiling Points of Aqueous Self-Ionization of Water and K 269 w ©Don Farrall/Getty Images Solutions 208 Osmosis, Osmotic Pressure, and Osmolarity 211 8.2 pH: A Measurement Scale for Acids and Bases 270 A Medical Perspective: Oral Rehydration Therapy 214 A Definition of pH 270 Measuring pH 271 6.5 Aqueous Solutions 214 Calculating pH 271 Water as a Solvent 214 A Medical Perspective: Drug Delivery 275 Kitchen Chemistry: Solubility, Surfactants, and the The Importance of pH and pH Control 275 Dishwasher 216 Concentration of Electrolytes in Solution 216 8.3 Reactions between Acids and Bases 276 Biological Effects of Electrolytes in Solution 219 Neutralization 276 A Medical Perspective: Hemodialysis 220 Polyprotic Substances 278 Green Chemistry: Hydrangea, pH, and Soil Chemistry 279 Chapter Map 221 Summary 221 8.4 Acid-Base Buffers 280 Questions and Problems 222 The Buffer Process 280 Multiple Concept Problems 225 Addition of Base or Acid to a Buffer Solution 280 Determining Buffer Solution pH 281 The Henderson-Hasselbalch Equation 284 7 Energy, Rate, and Control of Blood pH 285 Equilibrium 226 Green Chemistry: Acid Rain 286 7.1 Thermodynamics 227 8.5 Oxidation-Reduction Processes 287 The Chemical Reaction and Oxidation and Reduction 287 Energy 227 Voltaic Cells 288 The First Law of Thermodynamics 228 ©JonathanC Photography/ A Human Perspective: Lithium-Ion Batteries 290 Green Chemistry: Twenty-First Shutterstock Electrolysis 291 Century Energy 230 Applications of Oxidation and Reduction 291 The Second Law of Thermodynamics 231 Chapter Map 294 Free Energy 233 Summary 295 A Medical Perspective: Hot and Cold Packs 234 Questions and Problems 296 7.2 Experimental Determination of Energy Change in Reactions 235 Multiple Concept Problems 298 7.3 Kinetics 238 9 The Nucleus, Radioactivity, Chemical Kinetics 238 and Nuclear Medicine 299 Activation Energy and the Activated Complex 239 Factors That Affect Reaction Rate 240 9.1 Natural Radioactivity 300 Mathematical Representation of Reaction Rate 242 Alpha Particles 301 A Human Perspective: Too Fast or Too Slow? 243 Beta Particles and Positrons 301 ©Mark Kostich/Getty Images Contents vii Gamma Rays 302 10.3 Alkanes 337 Properties of Alpha, Beta, Positron, and Gamma Radiation 302 Structure 337 A Human Perspective: Origin of the Elements 303 Physical Properties 341 Alkyl Groups 341 9.2 Writing a Balanced Nuclear Equation 303 Nomenclature 343 Alpha Decay 303 Kitchen Chemistry: Alkanes in Our Food 344 Beta Decay 304 Green Chemistry: Biofuels: A Renewable Resource 346 Positron Emission 304 Constitutional or Structural Isomers 349 Gamma Production 304 Predicting Products of Nuclear Decay 305 10.4 Cycloalkanes 350 cis-trans Isomerism in Cycloalkanes 352 9.3 Properties of Radioisotopes 308 Nuclear Structure and Stability 308 10.5 Conformations of Alkanes and Cycloalkanes 354 Half-Life 308 Alkanes 354 Radiocarbon Dating 310 Green Chemistry: The Petroleum Industry and A Human Perspective: An Extraordinary Woman in Science 311 Gasoline Production 355 Cycloalkanes 355 9.4 Nuclear Power 312 10.6 Reactions of Alkanes and Cycloalkanes 356 Energy Production 312 Combustion 356 Nuclear Fission 312 Halogenation 357 Nuclear Fusion 314 A Medical Perspective: Polyhalogenated Hydrocarbons Breeder Reactors 314 Used as Anesthetics 359 Green Chemistry: Nuclear Waste Disposal 315 Chapter Map 360 9.5 Medical Applications of Radioactivity 315 Summary of Reactions 361 Cancer Therapy Using Radiation 315 Summary 361 Nuclear Medicine 316 Questions and Problems 362 Making Isotopes for Medical Applications 317 Multiple Concept Problems 367 A Medical Perspective: Magnetic Resonance Imaging 319 9.6 Biological Effects of Radiation 319 11 The Unsaturated Hydrocarbons: Radiation Exposure and Safety 319 Alkenes, Alkynes, and 9.7 Measurement of Radiation 321 Aromatics 369 Photographic Imaging 321 11.1 Alkenes and Alkynes: Structure and Computer Imaging 321 Physical Properties 370 The Geiger Counter 322 Film Badges 322 11.2 Alkenes and Alkynes: Units of Radiation Measurement 322 Nomenclature 372 Green Chemistry: Radon and Indoor Air Pollution 323 11.3 Geometric Isomers: A Consequence of Unsaturation 375 ©Cooperr/Shutterstock Chapter Map 325 A Medical Perspective: Killer Alkynes in Nature 376 Summary 326 Questions and Problems 327 11.4 Alkenes in Nature 382 Multiple Concept Problems 329 11.5 Reactions Involving Alkenes and Alkynes 384 Hydrogenation: Addition of H 384 2 Halogenation: Addition of X 388 2 Hydration: Addition of HO 390 ORGANIC CHEMISTRY 2 Hydrohalogenation: Addition of HX 393 Addition Polymers of Alkenes 394 10 An Introduction to Organic A Human Perspective: Life without Polymers? 395 Chemistry: The Saturated Green Chemistry: Plastic Recycling 396 Hydrocarbons 330 11.6 Aromatic Hydrocarbons 397 Structure and Properties 398 10.1 Strategies for Success in Organic Nomenclature 398 Chemistry 331 Kitchen Chemistry: Pumpkin Pie Spice: An Autumn Tradition 401 Prepare for Class 331 ©Pixtal/AGE Fotostock Polynuclear Aromatic Hydrocarbons 401 Make the Most of Class Time 331 Reactions Involving Benzene 402 11.7 Heterocyclic Aromatic Compounds 403 10.2 The Chemistry of Carbon 333 Kitchen Chemistry: Amazing Chocolate 404 Important Differences between Organic and Inorganic Compounds 333 Chapter Map 405 A Human Perspective: The Father of Summary of Reactions 406 Organic Chemistry 334 Summary 407 Families of Organic Compounds 334 Questions and Problems 407 Green Chemistry: Frozen Methane: Treasure or Threat? 336 Multiple Concept Problems 411 viii Contents 12 Alcohols, Phenols, Thiols, and 14 Carboxylic Acids and Carboxylic Ethers 412 Acid Derivatives 478 12.1 Alcohols: Structure and Physical 14.1 Carboxylic Acids 479 Properties 413 Structure and Physical Properties 479 Nomenclature 481 12.2 Alcohols: Nomenclature 416 IUPAC Names 416 Chemistry at the Crime Scene: ©Stockbyte/Getty Images Carboxylic Acids and the Body Farm 485 Common Names 417 ©Darren Greenwood/ Design Pics Some Important Carboxylic Acids 486 12.3 Medically Important Alcohols 419 Green Chemistry: Garbage Bags from Potato Peels? 487 Methanol 419 Reactions Involving Carboxylic Acids 490 Ethanol 419 14.2 Esters 493 Kitchen Chemistry: Sugar Alcohols and the Sweet Tooth 420 Structure and Physical Properties 493 2-Propanol 421 Nomenclature 493 1,2-Ethanediol 421 Reactions Involving Esters 495 1,2,3-Propanetriol 421 A Human Perspective: The Chemistry of Flavor and Fragrance 497 12.4 Reactions Involving Alcohols 421 A Human Perspective: Detergents 501 Preparation of Alcohols 421 Dehydration of Alcohols 424 14.3 Acid Chlorides and Acid Anhydrides 503 Oxidation Reactions 425 Acid Chlorides 503 Acid Anhydrides 503 12.5 Oxidation and Reduction in Living Systems 428 14.4 Nature’s High-Energy Compounds: Phosphoesters 12.6 Phenols 429 and Thioesters 507 Kitchen Chemistry: Spicy Phenols 430 A Medical Perspective: Esters for Appetite Control 509 A Medical Perspective: Resveratrol: Fountain of Youth? 431 Chapter Map 510 12.7 Ethers 432 Summary of Reactions 510 12.8 Thiols 435 Summary 511 Kitchen Chemistry: The Magic of Garlic 438 Questions and Problems 512 Multiple Concept Problems 516 Chapter Map 440 Summary of Reactions 441 15 Amines and Amides 518 Summary 441 Questions and Problems 442 15.1 Amines 519 Multiple Concept Problems 446 Structure and Physical Properties 519 Nomenclature 523 13 Aldehydes and Ketones 448 Medically Important Amines 526 13.1 Structure and Physical Reactions Involving Amines 528 ©ximagination/123RF Properties 449 Chemistry at the Crime Scene: Methamphetamine 530 A Human Perspective: Powerful Quaternary Ammonium Salts 532 Weak Attractions 450 15.2 Heterocyclic Amines 533 13.2 IUPAC Nomenclature and Source: FEMA/Andrea 15.3 Amides 535 Common Names 452 Booher, photographer Structure and Physical Properties 535 Naming Aldehydes 452 Kitchen Chemistry: Browning Reactions and Flavor: Naming Ketones 454 The Maillard Reaction 536 13.3 Important Aldehydes and Ketones 457 Nomenclature 536 Green Chemistry: Aldehydes, Stink Bugs, and Wine 457 Medically Important Amides 537 Reactions Involving Amides 539 13.4 Reactions Involving Aldehydes and Ketones 458 A Medical Perspective: Semisynthetic Penicillins 540 Preparation of Aldehydes and Ketones 458 Oxidation Reactions 460 15.4 A Preview of Amino Acids, Proteins, and Protein Synthesis 543 Reduction Reactions 462 15.5 Neurotransmitters 544 A Human Perspective: Alcohol Abuse and Antabuse 463 Catecholamines 544 Addition Reactions 465 Serotonin 544 Kitchen Chemistry: The Allure of Truffles 466 A Medical Perspective: Opiate Biosynthesis and the Mutant Keto-Enol Tautomers 469 Poppy 545 Chapter Map 471 Histamine 546 Summary of Reactions 472 γ-Aminobutyric Acid and Glycine 547 Summary 472 Acetylcholine 547 Questions and Problems 473 Green Chemistry: Neonicotinoid Pesticides and Honey Bees 548 Multiple Concept Problems 476 Nitric Oxide and Glutamate 548 Contents ix Chapter Map 549 17.2 Fatty Acids 595 Summary of Reactions 550 Structure and Properties 595 Summary 550 Omega-3 Fatty Acids 598 Questions and Problems 551 Eicosanoids: Prostaglandins, Leukotrienes, Multiple Concept Problems 555 and Thromboxanes 599 17.3 Glycerides 601 Neutral Glycerides 601 Chemical Reactions of Fatty Acids and Glycerides 603 BIOCHEMISTRY Phosphoglycerides 606 Chemistry at the Crime Scene: Adipocere and Mummies of Soap 608 16 Carbohydrates 556 17.4 Nonglyceride Lipids 608 16.1 Strategies for Success in Sphingolipids 608 Biochemistry 557 Steroids 610 A Medical Perspective: Disorders of Sphingolipid 16.2 Types of Carbohydrates 559 Metabolism 612 16.3 Monosaccharides 560 A Medical Perspective: Steroids and the Treatment A Medical Perspective: Chemistry ©Steve Gschmeissner/ of Heart Disease 613 through the Looking Glass 561 Science Source Waxes 615 16.4 Stereoisomers and Stereochemistry 562 17.5 Complex Lipids 615 Stereoisomers 562 17.6 The Structure of Biological Membranes 618 Rotation of Plane-Polarized Light 564 Fluid Mosaic Structure of Biological Membranes 618 The Relationship between Molecular Structure and A Medical Perspective: Liposome Delivery Systems 621 Optical Activity 565 Fischer Projection Formulas 565 Chapter Map 623 Racemic Mixtures 566 Summary 623 Diastereomers 567 Questions and Problems 624 Meso Compounds 568 Multiple Concept Problems 626 The d- and l- System of Nomenclature 569 16.5 Biologically Important Monosaccharides 569 18 Protein Structure Glucose 570 and Function 627 Fructose 574 Galactose 574 18.1 Biological Functions Ribose and Deoxyribose, Five-Carbon Sugars 575 of Proteins 628 Reducing Sugars 575 18.2 Protein Building Blocks: Kitchen Chemistry: The Chemistry of Caramels 576 The α-Amino Acids 629 ©Catmando/Shutterstock 16.6 Biologically Important Disaccharides 578 Structure of Amino Acids 629 Maltose 578 Stereoisomers of Amino Acids 629 Lactose 579 Classes of Amino Acids 629 A Medical Perspective: Human Milk Oligosaccharides 580 18.3 The Peptide Bond 632 Sucrose 580 A Human Perspective: The New Protein 635 16.7 Polysaccharides 581 18.4 The Primary Structure of Proteins 636 Starch 581 Glycogen 583 18.5 The Secondary Structure of Proteins 636 Cellulose 583 α-Helix 637 A Medical Perspective: Monosaccharide Derivatives and β-Pleated Sheet 638 Heteropolysaccharides of Medical Interest 584 18.6 The Tertiary Structure of Proteins 639 Chapter Map 586 A Medical Perspective: Collagen, Cosmetic Procedures, and Summary 587 Clinical Applications 641 Questions and Problems 588 18.7 The Quaternary Structure of Proteins 642 Multiple Concept Problems 590 18.8 An Overview of Protein Structure and Function 642 18.9 Myoglobin and Hemoglobin 644 17 Lipids and Their Functions Myoglobin and Oxygen Storage 644 in Biochemical Systems 592 Hemoglobin and Oxygen Transport 644 Oxygen Transport from Mother to Fetus 645 17.1 Biological Functions of Lipids 593 Sickle Cell Anemia 645 A Medical Perspective: Lifesaving Lipids 594 ©Juan Gaertner/Shutterstock 18.10 Proteins in the Blood 646
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