CONCISE I PRACTICAL I INTEGRATED General, Organic, and Biological CHEMISTRY Second Edition Laura Frost Florida Gulf Coast University Todd Deal Georgia Southern University With Contributions By Karen C. Timberlake PEARSON Boston Columbus Indianapolis New York San Francisco Upper Saddle River Amsterdam Cape Town Dubai London Madrid Milan Munich Paris Montreal Toronto Delhi Mexico City Sao Paulo Sydney Hong Kong Seoul Singapore Taipei Tokyo
Contents 1 Chemistry Basics Matter and Measurement 2 Discovering the Concepts; Classifying Matter 3 1.1 Classifying Matter: Mixture or Pure Substance 4 Mixtures 5 Pure Substances 6 Discovering the Concepts: The Periodic Table 7 1.2 Elements, Compounds, and the Periodic Table 7 Compounds 9 1.3 Math Counts 11 Units, Prefixes, and Conversion Factors 11 Converting Units 12 Significant Figures 13 Calculating Numbers and Rounding 15 Scientific Notation 16 Percent 18 Calculating Percent 19 1.4 Matter: The "Stuff" of Chemistry 20 Mass 20 Volume 21 Density 21 Temperature 24 Body Temperature 25 Energy 25 Heat and Specific Heat 27 States of Matter 27 1.5 Measuring Matter 29 Accuracy and Precision 29 Measurement in Health: Units and Dosing 30 Reading Lab Reports 31 Percents in Health 32 1.6 How Matter Changes 34 Physical Change 35 Chemical Reaction 35 Chemical Equations 36 Balancing a Chemical Equation 37 Summary 40 Study Guide Chapter 1 41 Key Terms 42 Important Equations 43 Additional Problems 43 Challenge Problems 46 Answers to Odd-Numbered Problems 46 2 Atoms and Radioactivity 48 2.1 Atoms and Their Components 49 Subatomic Particles 49 Structure of an Atom 49 2.2 Atomic Number and Mass Number 51 Atomic Number 51 Mass Number 51 Discovering the Concepts: Isotopes 53 2.3 isotopes and Atomic Mass 54 Atomic Mass 55 2.4 Radioactivity and Radioisotopes 56 Forms of Radiation 57 Biological Effects of Radiation 57 Discovering the Concepts: Radioactivity 59 2.5 Nuclear Equations and Radioactive Decay 59 Alpha Decay 60 Writing a Nuclear Decay Equation for Alpha Decay 60 Beta Decay and Positron Emission 61 Writing a Nuclear Decay Equation for Beta Decay 61 Gamma Decay 62 Producing Radioactive Isotopes 62 2.6 Radiation Units and Half-Lives 63 Radioactivity Units 63 Half Life 63 Determining Half-Life 64 2.7 Medical Applications for Radioisotopes 65 Radioisotopes and Cancer Treatment 66 Positron Emission Tomography 67 Summary 68 Study Guide Chapter 2 69 Key Terms 70
Additional Problems 70 Challenge Problems 72 Answers to Odd-Numbered Problems 72 3 Compounds Putting Particles Together 74 3.1 Electron Arrangements and the Octet Rule 75 The Octet Rule 77 3.2 In Search of an Octet, Part 1: Ion Formation 78 Trends in Ion Formation 79 Naming Ions 82 Important Ions in the Body 82 Discovering the Concepts: Ionic Compounds 84 3.3 Ionic Compounds Electron Give and Take 85 Formulas of Ionic Compounds 86 Checking a Chemical Formula 87 Predicting Number and Charge in an Ionic Compound 87 Naming Ionic Compounds 89 3.4 In Search of an Octet, Part 2: Covalent Bonding 90 Covalent Bond Formation 91 Formulas and Structures of Covalent Compounds 92 Naming Covalent Compounds 94 Naming Covalent Compounds 94 3.5 The Mole: Counting Atoms and Compounds 96 Avogadro's Number 97 Converting between Units 98 Molar Mass and Formula Weight 99 Calculating Molar Mass for a Compound 100 Finding the Number of Molecules in a Sample 101 Discovering the Concepts: Molecular Shape 101 3.6 Getting Covalent Compounds into Shape 103 Determining the Shape of a Molecule 103 Nonbonding Electrons and Their Effect on Molecular Shape 105 Molecular Shape of Larger Molecules 106 Discovering the Concepts: Bond Polarity 107 3.7 Electronegativity and Molecular Polarity 108 Electronegativity 108 Molecular Polarity 111 Summary 114 Study Guide Chapter 3 115 Key Terms 116 Additional Problems 116 Challenge Problems 119 Answers to Odd-Numbered Problems 119 4 Introduction to Organic Compounds 122 4.1 Alkanes: The Simplest Organic Compounds 124 Straight-Chain Alkanes 124 Cycloalkanes 126 Alkanes Are Nonpolar Compounds 127 Discovering the Concepts: Representing Molecules on Paper 128 4.2 Representing the Structures of Organic Compounds 129 Condensed Structural Formulas 129 Skeletal Structures 131 Drawing Skeletal Structures 132 Discovering the Concepts: Meet the Hydrocarbons 134 4.3 Families of Organic Compounds Functional Groups 135 Unsaturated Hydrocarbons Alkenes, Alkynes, and Aromatics 139 Pharmaceuticals Are Organic Compounds 142 Lipids Are Hydrocarbons Fatty Fatty Acids in Our Diets 145 4.4 Nomenclature of Simple Alkanes 146 Branched-Chain Alkanes 147 Naming Branched-Chain Alkanes 147 Haloalkanes 150 Cycloalkanes 150 4.5 Isomerism in Organic Compounds 152 Acids 143 Structural Isomers and Conformational Isomers 153
~\ Distinguishing Structural and Conformational Isomers 154 Cis-Trans Stereoisomers in Cycloalkanes and Alkenes 155 Unsaturated Fatty Acids Contain Cis Alkenes 158 Stereoisomers Chiral Molecules and Enantiomers 160 Identifying Chiral Carbons in a Molecule 162 5.6 Organic Addition Reactions to Alkenes 201 Hydrogenation 201 Hydration 202 Summary 204 Study Guide Chapter 5 205 Key Terms 206 Summary of Reactions 207 Additional Problems 207 Challenge Problems 210 Answers to Odd-Numbered Problems 210 The Consequences of Chirality 165 Summary 168 Study Guide Chapter 4 169 Key Terms 170 Additional Problems 171 Challenge Problems 174 Answers to Odd-Numbered Problems 174 6 Carbohydrates Life's Sweet Molecules 212 6.1 Classes of Carbohydrates 214 Fiber in Your Diet 214 5 Chemical Reactions m 5.1 Thermodynamics 179 Heat of Reaction 179 Activation Energy 181 Calorimetry: An Application of Thermodynamics 182 Energy Content in Food 183 Low-Calorie Foods 184 Discovering the Concepts: Reaction Energy Diagrams 185 5.2 Chemical Reactions: Kinetics 186 Factors Affecting Reaction Rates 186 Enzymes Are Biological Catalysts 187 Discovering the Concepts: Types of Chemical Reactions 188 5.3 Overview of Chemical Reactions 189 Types of Chemical Reactions 189 Reversible and Irreversible Reactions 190 Combustion 191 Distinguishing Chemical Reactions 192 Discovering the Concepts: Oxidation-Reduction Reactions 194 5.4 Oxidation and Reduction 196 Inorganic Oxidation and Reduction 196 Organic Oxidation and Reduction 197 Oxidation in Cells 198 5.5 Organic Reactions: Condensation and Hydrolysis 199 6.2 Functional Groups in Monosaccharides 215 Alcohol 215 Aldehyde 216 Ketone 216 Discovering the Concepts: Fischer Projections 218 6.3 Stereochemistry in Monosaccharides 219 Representing Stereoisomers The Fischer Projection 220 Drawing an Enantiomer in a Fischer Projection 222 Stereoisomers That Are Not Enantiomers 223 Important Monosaccharides 224 Discovering the Concepts: Ring Formation 227 6.4 Reactions of Monosaccharides 228 Ring Formation The Truth about Monosaccharide Structure 228 Drawing Pyranose Rings from Linear Monosaccharides 230 Oxidation-Reduction and Reducing Sugars 232 6.5 Disaccharides 236 Condensation and Hydrolysis Forming and Breaking Glycosidic Bonds 236 Naming Glycosidic Bonds 238 Three Important Disaccharides Maltose, Lactose, and Sucrose 239 Relative Sweetness of Sugars and Artificial Sweeteners 241 ; J vii
"A V viii 6.6 Polysaccharides 243 Storage Polysaccharides 243 Structural Polysaccharides 245 6.7 Carbohydrates and Blood 247 ABO Blood Types 247 Universal Donors and Acceptors 248 Heparin 249 Summary 250 Study Guide Chapter 6 251 Key Terms 252 Summary of Reactions 253 Additional Problems 254 Challenge Problems 256 Answers to Odd-Numbered Problems 257 7 What's the Attraction? State Changes, Solubility, and Lipids 260 Discovering the Concepts: The Attractive Forces 261 7.1 Types of Attractive Forces 263 London Forces 263 Dipole-Dipole Attractions 264 Hydrogen Bonding 265 Drawing Hydrogen Bonds 266 lon-dipole Attraction 268 Ionic Attraction 268 Identifying Attractive Forces in Compounds 269 Attractive Forces Keep Biomolecules in Shape 270 7.2 Liquids and Solids: Attractive Forces Are Everywhere 271 Heat and Attractive Forces 272 Boiling Points and Alkanes 273 The Unique Behavior of Water 275 Predicting Boiling Points 276 Discovering the Concepts: Solubility in Water 278 7.3 Attractive Forces and Solubility 280 The Golden Rule of Solubility 280 Predicting Solubility 280 How Soap Works 283 Predicting Solubility in Water 284 7.4 Gases: Attractive Forces Are Limited 285 Gases and Pressure 285 Pressure and Volume Boyle's Law 286 Boyle's Law 287 Boyle's Law and Breathing 288 Temperature and Volume Charles's Law 289 Charles's Law 290 7.5 Dietary Lipids and Trans Fats 291 Fats Are Solids 291 Oils Are Liquids 292 Partial Hydrogenation and Trans Fats 292 7.6 Attractive Forces and the Cell Membrane 295 A Look at Phospholipids 295 The Cell Membrane Is a Bilayer 296 Steroids in Membranes: Cholesterol 297 Summary 298 Study Guide Chapter 7 299 Key Terms 300 Additional Problems 301 Challenge Problems 303 Answers to Odd-Numbered Problems 303 8 Solution Chemistry How Sweet Is Your Tea? 306 8.1 Solutions Are Mixtures 307 States of Solutes and Solvents 307 Colloids and Suspensions 308 8.2 Formation of Solutions 309 Factors Affecting Solubility and Saturated Solutions 310 Gout, Kidney Stones, and Solubility 310 Solubility and Temperature 311 Solubility and Pressure Henry's Law 311 Discovering the Concepts: Electrolytes 314 8.3 Chemical Equations for Solution Formation 314 Strong Electrolytes 315 Nonelectrolytes 315 Weak Electrolytes 316 Balancing Hydration Equations 317 Ionic Solutions and Equivalents 318. )
^ Electrolytes in Blood Plasma 319 8.4 Concentrations 320 Millimoles per Liter (mmol/l) and Molarity (M) 321 Calculating Molarity 321 Percent (%) Concentration 323 Relationship to Other Common Units 324 Parts per Million (ppm) and Parts per 8.5 Dilution 326 Billion (ppb) 324 Using the Dilution Equation 327 Discovering the Concepts: Osmosis 328 8.6 Osmosis and Diffusion 329 Osmosis 329 Diffusion and Dialysis 331 Kidney Dialysis 332 8.7 Transport across Cell Membranes 333 Summary 336 Study Guide Chapter 8 337 Key Terms 338 Important Equations 339 Additional Problems 339 Challenge Problems 341 Answers to Odd-Numbered Problems 341 9 Acids, Bases, and Buffers in the Body 344 9.1 Acids and Bases Definitions 345 Acids 345 Bases 346 Acids and Bases Are Both Present in Aqueous Solution 346 9.2 Strong Acids and Bases 347 Neutralization 348 Completing a Neutralization Reaction 349 Antacids 350 9.3 Chemical Equilibrium 351 The Equilibrium Constant K 352 Effect of Concentration on Equilibrium LeChatelier's Principle 353 Effect of Temperature on Equilibrium 354 Discovering the Concepts: Weak Acids 356 9.4 Weak Acids and Bases 357 The Equilibrium Constant Ka 357 Conjugate Acids and Bases 358 Writing Weak Acid-Base Equations 360 Weak Acids, Oxygen Transport, and Le Chatelier's Principle 361 9.5 ph and the ph Scale 362 The Autoionization of Water, Kw 362 9.6 pka 366 [H30+], [OH-], and ph 363 Measuring ph 364 Calculating ph 364 Calculating [H30+] 365 9.7 Amino Acids: Common Biological Weak Acids 368 Discovering the Concepts: The Bicarbonate Buffer System 370 9.8 Buffers and Blood: The Bicarbonate Buffer System 371 Maintaining Physiological ph with Bicarbonate Buffer: Homeostasis 371 Summary 374 Study Guide Chapter 9 375 Key Terms 376 Additional Problems 376 Challenge Problems 378 Answers to Odd-Numbered Problems 378 10 Proteins Workers of the Cell 3so Discovering the Concepts: Characteristics of Amino Acids 381 10.1 Amino Acids A Second Look 382 Classification of Amino Acids 386 Discovering Peptide Bond 388 10.2 Protein Formation 388 the Concepts: Condensation and the Biological Condensation Reactions 388 Writing Condensation and Hydrolysis Products 389 Amides and the Peptide Bond 390 IX
10.3 The Three-Dimensional Structure of Proteins 393 Primary Structure 393 Secondary Structure 393 Tertiary Structure 394 Collagen and Vitamin C 397 Quaternary Structure 397 10.4 Denaturation of Proteins 399 10.5 Protein Functions 401 Proteins as Messengers, Receptors, and Transporters 401 Hemoglobin Your Body's Oxygen Transporter 402 Antibodies Your Body's Defense Protein 402 10.6 Enzymes Life's Catalysts 403 The Active Site 404 Enzyme-Substrate Models 405 Rates of Reaction 405 Discovering the Concepts: Factors That Affect Enzyme Activity 407 10.7 Factors That Affect Enzyme Activity 408 Substrate Concentration 409 ph 409 Temperature 410 Inhibitors 411 Antibiotics Inhibit Bacterial Enzymes 413 Summary 414 Study Guide Chapter 10 415 Key Terms 416 Additional Problems 417 Challenge Problems 420 Answers to Odd-Numbered Problems 420 11.2 Nucleic Acid Formation 434 Primary Structure: Nucleic Acid Sequence 434 Discovering the Concepts: The Unique Structure * of DNA 437 11.3 DNA 438 Secondary Structure: Complementary Base Pairing 438 Tertiary Structure: Chromosomes 440 11.4 RNA and Protein Synthesis 441 RNA Types and Where They Fit In 441 Discovering the Concepts: The Genetic Code 444 11.5 Putting It Together: The Genetic Code and Protein Synthesis 445 The Genetic Code 445 Protein Synthesis 446 11.6 Genetic Mutations 448 Sources of Mutations 449 11.7 Viruses 451 Retroviruses 452 HIV-1 and AIDS 453 11.8 Recombinant DNA Technology 454 Therapeutic Proteins 456 Genetically Modified Crops 456 Genetic Testing 456 Nuclear Transplantation Cloning an Organism 457 Summary 458 Study Guide Chapter 11 459 Key Terms 460 Additional Problems 460 Challenge Problems 462 Answers to Odd-Numbered Problems 462 11 Nucleic Acids Big Molecules with a Big Role 424 Discovering the Concepts: Components of Nucleotides 426 11.1 Components of Nucleic Acids 427 Nitrogenous Bases 427 Ribose and Deoxyribose 428 Condensation of the Components 428 Writing Condensation Products for Nucleotide Components 430 Naming Nucleotides 431 12 Food as Fuel A Metabolic Overview 464 Discovering the Concepts: Reaction Pathways 465 12.1 How Metabolism Works 466 Metabolic Pathways in the Animal Cell 468 12.2 Metabolically Relevant Nucleotides 470 ATP/ADP 471 NADH/NAD+ and FADH/FAD 471 Acetyl Coenzyme A and Coenzyme A 472
12.3 Digestion From Food Molecules to Hydrolysis Products 472 Carbohydrates 473 Fats 473 Proteins 475 12.4 Glycolysis From" Hydrolysis Products to Common Metabolites 476 The Chemical Reactions in Glycolysis 476 Regulation of Glycolysis 480 The Fates of Pyruvate 480 Fructose and Glycolysis 481 12.5 The Citric Acid Cycle Central Processing 483 Reactions of the Citric Acid Cycle 483 Citric Acid Cycle Summary 485 12.6 Electron Transport and Oxidative Phosphorylation 485 Electron Transport 486 Oxidative Phosphorylation 487 Thermogenesis Uncoupling ATP Synthase 488 12.7 ATP Production 489 Counting ATP from One Glucose 490 Discovering the Concepts: Fatty Acid Catabolism (Beta Oxidation) 492 12.8 Other Fuel Choices 493 Energy from Fatty Acids 493 Producing ATP from j3 Oxidation 494 Too Much Acetyl CoA Ketosis 496 Energy from Amino Acids 496 Putting It Together Linking the Pathways 498 Summary 500 Study Guide Chapter 12 501 Key Terms 502 Summary of Reactions 502 Additional Problems 503 Challenge Problems 504 Answers to Odd-Numbered Problems 504 Discovering the Concepts: ATP Production 489