FUNDAMENTALS OF GENERAL, ORGANIG, AND

BLOLOGIGAL CHEMISTRY

SIXTH EDITION

JOHN R. HOLUM Augsburg College

JOHN WILEY & SONS, INC. New York / Ghichester / Weinheim

Brisbane / Singapore / Toronto

CONTENTS

1 GOALS, METHODS, AND MEASUREMENTS

1.1 Chemistry and the Molecular Basis of Life 1.2 Facts, Hypotheses, and Theories in

Science 3 1.3 Properties and the States of Matter 4 1.4 Physical Quantities, Measurement, and

Significant Figures 6 1.5 Scientific Notation 14 1.6 Factor-Label Method in Galculations 19 1.7 Density and Specific Gravity 22 Summary 24 Review Exercises 25

2 MATTER AND ENERGY

This Chapter in Gontext 30 2.1 States and Kinds of Matter 30 2.2 Atoms, Chemical Symbols, and Equations 2.3 Kinetic and Potential Energy 38 2.4 Heat 40 2.5 Heat and Molecular Kinetic Energy 43 Summary 45 Review Exercises 46

29

3 ATOMIG THEORY AND THE PERIODIC

TABLE

This Chapter in Context 50 3.1 The Nuclear Atom 50 3.2 Periodic Law and Periodic Table 53 3.3 Electron Gonfigurations, an Overview 58 3.4 Electron Configurations and Atomic

Orbitals 60 Summary 69 Review Exercises 70

4 CHEMICAL COMPOUNDS AND

CHEMICAL BONDS

This Chapter in Context 75 4.1 Electron Transfers and Ionic Compounds 4.2 Monatomic Ions and the Octet Rule 81

49

74

4.3 Redox Reactions 85 4.4 Electron Sharing and Molecular

Compounds 87 4.5 Lewis Structures and the Octet Rule 89 4.6 Structures of Polyatomic Ions 96 4.7 Writing Lewis Structures of Molecules and

Polyatomic Ions 99 4.8 Shapes of Molecules 105 4.9 Polar Molecules 107 Summary 111 Review Exercises 112

5 QUANTITATIVE RELATIONSHIPS IN

CHEMICAL REACTIONS 117

This Chapter in Gontext 118 5.1 Mole Concept 118 5.2 Atomic, Formula, and Molecular Masses 119

33 5.3 Balanced Chemical Equations and Stoichiometry 124

5.4 Reactions in Solution 131 5.5 Molar Concentration 133 5.6 Preparing Dilute Solutions from Goncentrated

Solutions 138 Summary 141 Review Exercises 141

75

6 STATES OF MATTER AND THE

KINETIC THEORY 146

This Chapter in Gontext 147 6.1 Gaseous State 147 6.2 Pressure-Volume-Temperature Relationships

for a Fixed Amount of Gas 148 6.3 Ideal Gas Law 153 6.4 Dalton's Law of Partial Pressures 156 6.5 Kinetic Theory of Gases Revisited 159 6.6 Liquid State 160 6.7 Vapor Pressure, Dynamic Equilibria, and

Ghanges of State 162 6.8 Water and the Hydrogen Bond 165 6.9 Solid State 169 Summary 171 Review Exercises 172

xii CONTENTS

7 SOLUTIONS, AND GOLLOIDS 177

This Chapter in Context 178 7.1 lypes of Homogeneous Mixtures 178 7.2 Aqueous Solutions and How They Form 180 7.3 Solubilities of Gases 185 7.4 Percentage Concentration Expressions 189 7.5 Osmosis and Dialysis 191 7.6 Dialysis and the Bloodstream 195 Summary 198 Review Exercises 198

8 ACIDS, BASES, AND IONIC COMPOUNDS 202

This Chapter in Context 203 8.1 Electrolytes 203 8.2 Acids and Bases as Electrolytes 206 8.3 Chemical Properties of Aqueous Acids and

Bases 213 8.4 Strengths of Br0nsted Acids and Bases—

A Qualitative View 223 8.5 Salts 229 Summary 239 Review Exercises 240

9 REACTION KINETICS AND CHEMICAL

EQUILIBRIA. ACID-BASE EQUILIBRIA 246

This Chapter in Context 247 9.1 Factors That Affect Reaction Rates 247 9.2 Kinetic Theory and Chemical Reactions 251 9.3 Chemical Equilibria Revisited 255 9.4 Ion Product Constant of Water 257 9.5 pH Concept 258 9.6 Acid Ionization Constants 264 9i7 Base Ionization Constants 267 9.8 pfta and pKh Concepts 271 9.9 Buffers 273 9.10 Some Quantitative Aspects of Buffers 277 9.11 Acid-Base Titrations 284 Summary 286 Review Exercises 288

10 RADIOACTIVITY AND NUCLEAR

CHEMISTRY

This Chapter in Context 294 10.1 Atomic Radiation 294

293

10.2 Ionizing Radiation—Dangers and Precautions 299

10.3 Units to Describe and Measure Radiation 304 10.4 Synthetic Radionuclides 306 10.5 Radiation Technology in the Food

Industry 307 10.6 Radiation Technology in Medicine 309 10.7 Atomic Energy and Radionuclides 312 Summary 318 Review Exercises 319

11 ORGANIC CHEMISTRY. SATURATED

HYDROCARBONS 323

This Chapter in Context 324 11.1 Organic and Inorganic Compounds 324 11.2 Some Structural Features of Organic

Compounds 325 11.3 Isomerism 334 11.4 Functional Groups 336 11.5 Alkanes and Cycloalkanes 339 11.6 Naming the Alkanes and Cycloalkanes 344 11.7 Chemical Properties of Alkanes 351 Summary 356 Review Exercises 357

12 UNSATURATED HYDROCARBONS 361

This Chapter in Context 362 12.1 Occurrence 362 12.2 Naming the Alkenes 363 12.3 Geometrie Isomers 367 12.4 Addition Reactions of the Double Bond 369 12.5 How Addition Reactions Occur 378 12.6 Addition Polymers 383 12.7 Benzene Ring and Aromatic Properties 386 12.8 Naming Compounds of Benzene 391 Summary 392 Review Exercises 394

13 ALCOHOLS, PHENOLS, ETHERS, AND

THIOALCOHOLS

This Chapter in Context 400 13.1 Occurrence, Types, and Names of

Alcohols 400 13.2 Physical Properties of Alcohols 407

399

CONTENTS xiii

13.3 Chemical Properties of Alcohols 409 13.4 Phenols 415 13.5 Ethers 417 13.6 Thioalcohols and Disulfides 420 Summary 422 Review Exercises 423

14 ALDEHYDES AND KETONES 428

This Chapter in Context 429 14.1 Structures and Physical Properties of

Aldehydes and Ketones 429 14.2 Naming Aldehydes and Ketones 430 14.3 Oxidation of Aldehydes and Ketones 434 14.4 Reduction of Aldehydes and Ketones 436 14.5 Reactions of Aldehydes and Ketones with

Alcohols 439 Summary 445 Review Exercises 446

15 CARBOXYLIC ACIDS AND ESTERS 452

This Chapter in Context 453 15.1 Occurrences, Names, and Physical Properties

of Carboxylic Acids 453 Acidity of Carboxylic Acids 456 Conversion of Carboxylic Acids to Esters 459 Occurrence, Names, and Physical Properties of Esters 463 Some Reactions of Esters 467 Organophosphate Esters and Anhydrides 470

Summary 474 Review Exercises

15.2 15.3 15.4

15.5 15.6

474

16 AMINES AND AMIDES 479

This Chapter in Context 480 16.1 Occurrence, Names, and Physical Properties

of Amines 480 16.2 Chemical Properties of Amines 482 16.3 Amides of Carboxylic Acids 487 Summary 493 Review Exercises 493

17 STEREOISOMERISM

This Chapter in Context 17.1 Types of Isomerism

498

499 499

17.2 Molecular Chirality 500 17.3 Optical Activity 509 Summary 514 Review Exercises 514

18 GARBOHYDRATES

This Chapter in Context 517 18.1 Biochemistry—An Overview 517

Introduction to Monosaccharides 518 D- and L-Families of Carbohydrates 521 Cyclic Forms of Monosaccharides 526 Disaccharides 534 Polysaccharides 537

Summary 541 Review Exercises

516

18.2 18.3 18.4 18.5 18.6

541

19 LlPIDS

This Chapter in Context 546 19.1 What Lipids Are 546 19.2 Chemical Properties of Triacylglycerols 19.3 Phospholipids 555 19.4 Steroids 559 19.5 Cell Membranes—TheirLipid

Gomponents 562 Summary 564 Review Exercises 564

545

552

20 PROTEINS 567

This Chapter in Context 568 20.1 Amino Acids. The Building Blocks of

Proteins 568 Overview of Protein Structure Primary Structures of Proteins Secondary Structures of Proteins Tertiary Structures of Proteins Quaternary Structures of Proteins

20.2 20.3 20.4 20.5 20.6 20.7 20.8

574 575

578 581

582 Common Properties of Proteins 585 Cell Membranes Revisited—Glycoprotein Components 590

20.9 Classes of Proteins 596 Summary 597 Review Exercises 598

xiv CONTENTS

21 ENZYMES 601

This Ghapter in Gontext 602 21.1 The Nature of Enzymes 602 21.2 Enzyme-Substrate Complex 606 21.3 Kinetics of Simple Enzyme-Substrate

Interactions 608 21.4 Regulation of Enzymes 612 21.5 Enzymes in Medicine 616 Summary 619 Review Exercises 620

Summary 701 Review Exercises 702

25 BlOCHEMICAL ENERGETIGS 705

This Ghapter in Context 706 25.1 Energy for Living—An Overview 706 25.2 Gitric Acid Gycle 711 25.3 Respiratory Chain 715 Summary 722 Review Exercises 723

HORMONES AND NEUROTRANSMITTERS 622

This Ghapter in Context 623 22.1 Chemical Communication—

How It Works 623 22.2 Hormones and Neurotransmitters 627 22.3 Retrograde Messengers 636 Summary 638 Review Exercises 638

23 EXTRACELLULAR FLUIDS OF THE BODY 640

This Chapter in Gontext 641 23.1 Digestive Juices 641 23.2 Blood and the Absorption of Nutrients by

Cells 645 23.3 Blood and the Exchange of Respiratory

Gases 651 23.4 Acid-Base Balance of the Blood 657 23.5 Blood and the Functions of the Kidneys 662 Summary 663 Review Exercises 664

26 METABOLISM O F GARBOHYDRATES 725

This Chapter in Context 726 26.1 Glycogen Metabolism 726 26.2 Glucose Tolerance 731 26.3 Gatabolism of Glucose 734 26.4 Gluconeogenesis 739 Summary 741 Review Exercises 742

27 METABOLISM O F LIPIDS 744

This Chapter in Context 745 27.1 Absorption and Distribution of Lipids 745 27.2 Storage and Mobilization of Lipids 747 27.3 Oxidation of Fatty Acids 750 27.4 Biosynthesis of Fatty Acids 753 27.5 Biosynthesis of Gholesterol 756 27.6 Ketoacidosis 759 Summary 762 Review Exercises 763

24 NUGLEIC ACIDS 667

This Chapter in Context 668 24.1 Heredity and the Cell 668 24.2 Structure of Nucleic Acids 670 24.3 Ribonucleic Acids 677 24.4 mRNA-Directed Polypeptide Synthesis 24.5 Viruses 687 24.6 Recombinant DNA Technology and Genetic

Engineering 690 24.7 Hereditary Diseases and Genetic

Engineering 697

28 METABOLISM OF NITROGEN

COMPOUNDS 765

This Ghapter in Gontext 766 28.1 Synthesis of Amino Acids in the Body

682 28.2 Gatabolism of Amino Acids 767 28.3 Formation of Urea 773 28.4 Gatabolism of Other Nitrogen

Compounds 775 Summary 778 Review Exercises 778

766

CONTENTS XV

29 NUTRITION

This Ghapter in Gontext 781 29.1 General Nutritional Requirements 781 29.2 Protein Requirements 785 29.3 Vitamins 789 29.4 Minerals and Trace Elements in

Nutrition 795 Summary 798 Review Exercises 799

APPENDIGES

A Mathematical Goncepts A-l B Electron Gonfigurations of the Elements B-l

C Some Rules for Naming Inorganic Compounds C-l

D Three Organic Reaction Mechanisms D-l E Answers to Practice Exercises and Selected Review

Exercises E-l

GLOSSARY G-l

PHOTO GREDITS P-I

INDEX M