Preview ISE General, Organic, Biological Chemistry (ISE HED WCB CHEMISTRY) by Janice Gorzynski Smith Dr. (2021)

Preview ISE General, Organic, Biological Chemistry (ISE HED WCB CHEMISTRY) by Janice Gorzynski Smith Dr. (2021) Preview ISE General, Organic, Biological Chemistry (ISE HED WCB CHEMISTRY) by Janice Gorzynski Smith Dr. (2021) Preview ISE General, Organic, Biological Chemistry (ISE HED WCB CHEMISTRY) by Janice Gorzynski Smith Dr. (2021) Preview ISE General, Organic, Biological Chemistry (ISE HED WCB CHEMISTRY) by Janice Gorzynski Smith Dr. (2021)

page i

General, Organic, & Biological

CHEMISTRY

Fifth Edition

Janice Gorzynski Smith

University of Hawai‘i at Ma-noa

GENERAL, ORGANIC, & BIOLOGICAL CHEMISTRY

Published by McGraw Hill LLC, 1325 Avenue of the Americas, New York, NY 10121 Copyright ©2022 by McGrawHill LLC All rights reserved Printed in the United States of America Previous editions ©2019, 2016, and 2013 Nopart of this publication may be reproduced or distributed in any form or by any means, or stored in a database orretrieval system, without the prior written consent of McGraw Hill LLC, 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 UnitedStates

This book is printed on acid-free paper

1 2 3 4 5 6 7 8 9 LWI 24 23 22 21

ISBN 978-1-264-64741-5

MHID 1-264-64741-7

Cover Image: Douglas Klug/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 notindicate an endorsement by the authors or McGraw Hill LLC, and McGraw Hill LLC does not guarantee the accuracy

of the information presented at these sites

mheducation.com/highered

page iii

About the Author

Daniel C Smith

Janice Gorzynski Smith was born in Schenectady, New York She received an A.B degree summa cum laude

in chemistry at Cornell University and a Ph.D in Organic Chemistry from Harvard University under the direction ofNobel Laureate E J Corey During her tenure with the Corey group, she completed the total synthesis of the plantgrowth hormone gibberellic acid

Following her postdoctoral work, Jan joined the faculty of Mount Holyoke College where she was employed for 21years During this time she was active in teaching chemistry lecture and lab courses, conducting a research program inorganic synthesis, and serving as department chair Her organic chemistry class was named one of Mount Holyoke’s

“Don’t-miss courses” in a survey by Boston magazine After spending two sabbaticals amidst the natural beauty and

diversity in Hawai‘i in the 1990s, Jan and her family moved there permanently in 2000 Most recently, she has served

as a faculty member at the University of Hawai‘i at Mānoa In 2003, she received the Chancellor’s Citation forMeritorious Teaching

Jan resides in Hawai‘i with her husband Dan, an emergency medicine physician, pictured with her hiking in Laos in

2019 She has four children and nine grandchildren When not teaching, writing, or enjoying her family, Jan bikes,hikes, snorkels, and scuba dives in sunny Hawai‘i, and time permitting, enjoys travel and Hawaiian quilting

D edicated to my family, especially Max, Oliver, Alijah, Koa, Logan, Elliott, Penelope, Otis, and Isabelle

About the cover Giant kelp, a type of marine algae that grows in dense forests in cold ocean waters, is a source of

atmospheric chloromethane (CH3Cl), a simple organic compound that contains the halogen chlorine Chloromethane, acolorless gas with a faint odor, is also formed in forests by wood-rotting fungi and is released during volcaniceruptions Because it is a key compound in the manufacture of polymers and drugs, chloromethane is extensively

produced by the chemical industry, but most of the chloromethane in the atmosphere is natural in origin In General,

Organic, & Biological Chemistry, we learn about the chemical properties of compounds like chloromethane.

Matter and Measurement

Atoms and the Periodic Table

Ionic Compounds

Covalent Compounds

Chemical Reactions

Energy Changes, Reaction Rates, and Equilibrium

Gases, Liquids, and Solids

Organic Compounds That Contain Oxygen, Halogen, or Sulfur

The Three-Dimensional Shape of Molecules

Aldehydes and Ketones

Carboxylic Acids, Esters, and Amides

Amines and Neurotransmitters

Lipids

Carbohydrates

Amino Acids, Proteins, and Enzymes

Nucleic Acids and Protein Synthesis

Metabolism and Energy Production

Carbohydrate, Lipid, and Protein Metabolism

Available online only in McGraw-Hill Connect® and CreateTM

Body Fluids

1.5A1.5B1.5C

1.6

1.6A1.6B

1.7

1.7A1.7B1.7C

Matter and Measurement 1

Chemistry—The Science of Everyday Experience 2 States of Matter 3

Classification of Matter 5 Measurement 8

The Metric System 8Measuring Length 10Measuring Mass 10Measuring Volume 11Significant Figures 12Determining the Number of Significant Figures 12Using Significant Figures in Multiplication and Division 13Using Significant Figures in Addition and Subtraction 15Scientific Notation 16

Writing Numbers in Scientific Notation 16Using a Scientific Calculator for Numbers in Scientific Notation 19Problem Solving Using Conversion Factors 19

Conversion Factors 19Solving a Problem Using One Conversion Factor 20Solving a Problem Using Two or More Conversion Factors 22FOCUS ON HEALTH & MEDICINE: Problem Solving Using Clinical Conversion Factors 23

Temperature 25

1.10A1.10B

2.1

2.1A2.1B2.1C

2.2

2.3

2.3A2.3B2.3C

2.4

2.4A2.4B

2.5

2.6

2.6A2.6B

Key Terms 29Key Concepts 30Key Equations 30Key Skills 31Problems 32Challenge Problems 35Answers to Problems 36

Daniel C Smith

Atoms and the Periodic Table 38

Elements 39Elements and the Periodic Table 40FOCUS ON THE HUMAN BODY: The Elements of Life 41Compounds 42

Structure of the Atom 44 Isotopes 48

Isotopes, Atomic Number, and Mass Number 48Atomic Weight 51

FOCUS ON HEALTH & MEDICINE: Isotopes in Medicine 52The Periodic Table 52

Basic Features of the Periodic Table 52Characteristics of Groups 1A, 2A, 7A, and 8A 54Electronic Structure 56

Electronic Configurations 59First-Row Elements (Period 1) 60Second-Row Elements (Period 2) 61

2.7

2.7A2.7B

2.8

2.8A2.8B

3.1

3.2

3.2A3.2B3.2C3.2D

3.3

3.3A3.3B

3.4

3.4A3.4B3.4C

Key Terms 70Key Concepts 71Key Skills 72Problems 73Challenge Problems 77Answers to Problems 77

Mark Dierker/McGraw-Hill

Ionic Compounds 79

Introduction to Bonding 80 Ions 82

Cations and Anions 82Relating Group Number to Ionic Charge for Main Group Elements 85Metals with Variable Charge 87

FOCUS ON THE HUMAN BODY: Important Ions in the Body 88Ionic Compounds 90

Formulas for Ionic Compounds 91FOCUS ON HEALTH & MEDICINE: Ionic Compounds in Consumer Products 93Naming Ionic Compounds 93

Naming Cations 93Naming Anions 94Naming Ionic Compounds with Cations from Main Group Metals 95

3.5

3.6

3.6A3.6B3.6C3.6D

4.1

4.1A4.1B

4.2

4.2A4.2B

4.3

4.3A4.3B

4.4

4.4A4.4B

Key Terms 103Key Concepts 103Key Skills 104Problems 105Challenge Problems 108Answers to Problems 109

Buttchi 3 Sha Life/Shutterstock

Covalent Compounds 111

Introduction to Covalent Bonding 112Covalent Bonding and the Periodic Table 113FOCUS ON THE HUMAN BODY: Covalent Molecules and the Cardiovascular System 115Lewis Structures 116

Drawing Lewis Structures 116Multiple Bonds 118

Exceptions to the Octet Rule 120Elements in Group 3A 120

Elements in the Third Row 120Resonance 121

Drawing Resonance Structures 121FOCUS ON THE ENVIRONMENT: Ozone 123

4.6

4.6A4.6B4.6C

5.2

5.3

5.3A5.3B

5.4

5.4A5.4B5.4C

FOCUS ON HEALTH & MEDICINE: Covalent Drugs and Medical Products 132

Chapter Review 135

Key Terms 135Key Concepts 135Key Skills 136Problems 137Challenge Problems 141Answers to Problems 142

Jill Braaten

Chemical Reactions 144

Introduction to Chemical Reactions 145General Features of Physical and Chemical Changes 145Writing Chemical Equations 147

Balancing Chemical Equations 149 Types of Reactions 154

Combination and Decomposition Reactions 154Replacement Reactions 156

Oxidation and Reduction 159General Features of Oxidation–Reduction Reactions 159Examples of Oxidation–Reduction Reactions 161FOCUS ON HEALTH & MEDICINE: Pacemakers 162

5.6

5.6A5.6B5.6C

5.7

5.8

5.8A5.8B

5.9

5.9A5.9B5.9C

5.10

5.10A5.10B5.10C

Calculating Percent Yield 177Calculating Percent Yield from Grams of Reactant 178FOCUS ON HEALTH & MEDICINE: The Importance of Percent Yield in the PharmaceuticalIndustry 180

Limiting Reactants 181Determining the Limiting Reactant 181Using the Limiting Reactant to Determine How Much Product Is Formed 183Determining the Limiting Reactant Using the Number of Grams 184

Chapter Review 185

Key Terms 185Key Concepts 186Key Skills 186Problems 188Challenge Problems 194Answers to Problems 194

Smereka/Shutterstock

Energy Changes, Reaction Rates, and Equilibrium 197

Energy 198The Units of Energy 198

6.2

6.2A6.2B

6.3

6.4

6.4A6.4B6.4C6.4D

6.5

6.5A6.5B6.5C

6.6

6.6A6.6B6.6C

Bond Dissociation Energy 201

Calculations Involving ΔH Values 203

Energy Diagrams 205 Reaction Rates 208How Concentration and Temperature Affect Reaction Rate 208Catalysts 209

FOCUS ON THE HUMAN BODY: Lactase, a Biological Catalyst 210FOCUS ON THE ENVIRONMENT: Catalytic Converters 211

Equilibrium 211The Equilibrium Constant 213The Magnitude of the Equilibrium Constant 214Calculating the Equilibrium Constant 216

Le Châtelier’s Principle 218Concentration Changes 219Temperature Changes 221Pressure Changes 222FOCUS ON THE HUMAN BODY: Body Temperature 224Chapter Review 225

Key Terms 225Key Concepts 225Key Equations 226Key Skills 226Problems 227Challenge Problems 232Answers to Problems 232

Daniel C Smith

Gases, Liquids, and Solids 235

The Three States of Matter 236

Boyle’s Law—How the Pressure and Volume of a Gas Are Related 240Charles’s Law—How the Volume and Temperature of a Gas Are Related 242Gay–Lussac’s Law—How the Pressure and Temperature of a Gas Are Related 244The Combined Gas Law 246

Avogadro’s Law—How Volume and Moles Are Related 247

The Ideal Gas Law 250

Dalton’s Law and Partial Pressures 253

Intermolecular Forces, Boiling Point, and Melting Point 255

London Dispersion Forces 255Dipole–Dipole Interactions 256Hydrogen Bonding 256

Boiling Point and Melting Point 258The Liquid State 260

Vapor Pressure 260Viscosity and Surface Tension 261The Solid State 262

Specific Heat 263

Energy and Phase Changes 266

Converting a Solid to a Liquid 266Converting a Liquid to a Gas 268Converting a Solid to a Gas 269Heating and Cooling Curves 270

Heating Curves 270Cooling Curves 271Combining Energy Calculations 272Chapter Review 273

Key Terms 273

Key Concepts 274

Key Equations—The Gas Laws 274

Key Skills 275

8.1A8.1B

8.2

8.2A8.2B

8.3

8.3A8.3B

8.4

8.4A8.4B

8.5

8.5A8.5B8.5C8.5D

8.6

8.7

8.8

8.8A8.8B

8.9

8

page x

Problems 276Challenge Problems 282Answers to Problems 283

Science Photo Library/Alamy Stock Photo

Solutions 285

Mixtures 286Solutions 286Colloids and Suspensions 287Electrolytes and Nonelectrolytes 288Classification 288

Equivalents 289Solubility—General Features 291Basic Principles 291

Ionic Compounds—Additional Principles 294Solubility—Effects of Temperature and Pressure 295Temperature Effects 295

Pressure Effects 295Concentration Units—Percent Concentration 296Weight/Volume Percent 296

Volume/Volume Percent 298Using a Percent Concentration as a Conversion Factor 298Parts Per Million 300

Concentration Units—Molarity 301 Dilution 304

Colligative Properties 307Boiling Point Elevation 307Freezing Point Depression 308Osmosis and Dialysis 310

9.1

9.1A9.1B

9.2

9.3

9.3A9.3B

9.4

9.5

9.6

9.6A9.6B9.6C

9.7

9.7A9.7B

9

Osmotic Pressure 310FOCUS ON THE HUMAN BODY: Osmosis and Biological Membranes 312FOCUS ON HEALTH & MEDICINE: Dialysis 313

Chapter Review 315

Key Terms 315Key Concepts 315Key Equations—Concentration 316Key Skills 316

Problems 318Challenge Problems 323Answers to Problems 323

Mark Dierker/McGraw-Hill

Acids and Bases 325

Introduction to Acids and Bases 326Brønsted–Lowry Acids 327

Brønsted–Lowry Bases 329The Reaction of a Brønsted–Lowry Acid with a Brønsted–Lowry Base 331 Acid and Base Strength 334

Relating Acid and Base Strength 334Using Acid Strength to Predict the Direction of Equilibrium 340Equilibrium and Acid Dissociation Constants 341

The Dissociation of Water 343 The pH Scale 346

Calculating pH 346Calculating pH Using a Calculator 348FOCUS ON THE HUMAN BODY: The pH of Body Fluids 350Common Acid–Base Reactions 350

Reaction of Acids with Hydroxide Bases 351Reaction of Acids with Bicarbonate and Carbonate 352

9.9

9.10

9.10A9.10B9.10C

9.11

10

10.1

10.1A10.1B

10.2

10.2A10.2B10.2C10.2D

10.3

10.3A10.3B

Chapter Review 363

Key Terms 363Key Concepts 363Key Equations 364Key Skills 364Problems 365Challenge Problems 370Answers to Problems 370

ClarkandCompany/Getty Images

Nuclear Chemistry 373

Introduction 374Isotopes 374Types of Radiation 376Nuclear Reactions 377Alpha Emission 377Beta Emission 378Positron Emission 380Gamma Emission 381Half-Life 382

General Features 383Archaeological Dating 385Detecting and Measuring Radioactivity 386

10.5

10.5A10.5B10.5C

10.6

10.6A10.6B

11.5

11.5A

Measuring the Radioactivity in a Sample 386FOCUS ON HEALTH & MEDICINE: The Effects of Radioactivity 388Measuring Human Exposure to Radioactivity 388

FOCUS ON HEALTH & MEDICINE: Medical Uses of Radioisotopes 389Radioisotopes Used in Diagnosis 389

Radioisotopes Used in Treatment 390Positron Emission Tomography—PET Scans 391Nuclear Fission and Nuclear Fusion 391Nuclear Fission 392

Nuclear Fusion 393FOCUS ON HEALTH & MEDICINE: Medical Imaging Without Radioactivity 395

Chapter Review 396

Key Terms 396Key Concepts 396Key Skills 396Problems 397Challenge Problems 401Answers to Problems 401

Kzenon/Alamy stock Photo

Introduction to Organic Molecules and Functional Groups 404

Introduction to Organic Chemistry 405 Characteristic Features of Organic Compounds 406 Shapes of Organic Molecules 409

Drawing Organic Molecules 414Condensed Structures 414

Skeletal Structures 417Functional Groups 420Hydrocarbons 421

11.6

11.6A11.6B11.6C

11.7

11.7A11.7B

12

12.1

12.2

12.2A12.2B12.2C12.2D

12.3

12.3A12.3B

12.4

12.4A12.4B

page xii

Compounds Containing a Single Bond to a Heteroatom 422

Compounds Containing a CO Group 423

Properties of Organic Compounds 428Polarity 428

Solubility 430FOCUS ON THE ENVIRONMENT: Environmental Pollutants 432FOCUS ON HEALTH & MEDICINE: Vitamins 433Vitamin A 433

Vitamin C 434Chapter Review 435

Key Terms 435Key Concepts 436Key Skills 437Problems 438Challenge Problems 443Answers to Problems 444

Daniel C Smith

Alkanes 447

Introduction 448 Simple Alkanes 449Acyclic Alkanes Having Fewer Than Five Carbons 449Acyclic Alkanes Having Five or More Carbons 451Classifying Carbon Atoms 453

Bond Rotation and Skeletal Structures for Acyclic Alkanes 454

An Introduction to Nomenclature 455The IUPAC System of Nomenclature 455FOCUS ON HEALTH & MEDICINE: Naming New Drugs 455Alkane Nomenclature 456

Naming Substituents 456Naming an Acyclic Alkane 457

12.5A12.5B

13.4

13.5

13.6

13.6A13.6B13.6C

Cycloalkanes 461Simple Cycloalkanes 461Naming Cycloalkanes 462FOCUS ON THE ENVIRONMENT: Methane and Other Fossil Fuels 464 Physical Properties 466

FOCUS ON THE ENVIRONMENT: Combustion 466 Halogenation of Alkanes 468

Chapter Review 469

Key Terms 469Key Concepts 469Key Reactions 470Key Skills 470Problems 471Challenge Problems 475Answers to Problems 475

Hin255/iStock/Getty Images

Unsaturated Hydrocarbons 478

Alkenes and Alkynes 479 Nomenclature of Alkenes and Alkynes 481 Cis–Trans Isomers 484

Stereoisomers—A New Class of Isomer 484FOCUS ON HEALTH & MEDICINE: Saturated and Unsaturated Fatty Acids 488Interesting Alkenes in Food and Medicine 490

FOCUS ON HEALTH & MEDICINE: Oral Contraceptives 490 Reactions of Alkenes 492

Addition of Hydrogen—Hydrogenation 493Addition of Halogen—Halogenation 494Addition of Hydrogen Halides—Hydrohalogenation 494

13.7

13.8

13.8A13.8B

13.9

13.10

13.10A13.10B13.10C13.10D

13.11

13.12

13.13

13.13A13.13B13.13C

Synthetic Polymers 499FOCUS ON THE ENVIRONMENT: Polymer Recycling 502Aromatic Compounds 503

Nomenclature of Benzene Derivatives 504Monosubstituted Benzenes 504

Disubstituted Benzenes 505Polysubstituted Benzenes 505Aromatic Compounds with More Than One Ring 506FOCUS ON HEALTH & MEDICINE: Aromatic Drugs, Sunscreens, and Carcinogens 507

FOCUS ON HEALTH & MEDICINE: Phenols as Antioxidants 508 Reactions of Aromatic Compounds 509

Chlorination and the Synthesis of the Pesticide DDT 509FOCUS ON HEALTH & MEDICINE: Nitration and Sulfa Drugs 510Sulfonation and Detergent Synthesis 511

Chapter Review 512

Key Terms 512Key Concepts 512Key Reactions 513Key Skills 513Problems 515

Challenge Problems 520Answers to Problems 520

Ed Reschke

Organic Compounds That Contain Oxygen, Halogen, or Sulfur 524

Introduction 525 Structure and Properties of Alcohols 527

14.4

14.5

14.5A14.5B

14.6

14.6A14.6B

14.7

14.7A14.7B

14.8

14.9

14.9A14.9B14.9C14.9D

14.10

15

Nomenclature of Alcohols 529 Interesting Alcohols 531

Reactions of Alcohols 533Dehydration 533

Oxidation 535FOCUS ON HEALTH & MEDICINE: Ethanol, the Most Widely Abused Drug 537

The Metabolism of Ethanol 537Health Effects of Alcohol Consumption 538Structure and Properties of Ethers 539Physical Properties 540

Naming Ethers 541FOCUS ON HEALTH & MEDICINE: Ethers as Anesthetics 542 Alkyl Halides 543

Physical Properties 543Nomenclature 544Interesting Alkyl Halides 545FOCUS ON THE ENVIRONMENT: Alkyl Halides and the Ozone Layer 545Organic Compounds That Contain Sulfur 547

Chapter Review 549

Key Terms 549Key Concepts 549Key Reactions 549Key Skills 550Problems 551Challenge Problems 556Answers to Problems 556

PeskyMonkey/Getty Images

The Three-Dimensional Shape of Molecules 559

15.2

15.2A15.2B15.2C

15.3

15.3A15.3B

15.4

15.4A15.4B

15.5

15.5A15.5B

15.6

15.7

15.7A15.7B

The Chirality of Molecules 563Chirality in Nature 564

Chirality Centers 564Locating Chirality Centers 564Drawing a Pair of Enantiomers 567Chirality Centers in Cyclic Compounds 568Locating Chirality Centers on Ring Carbons 568FOCUS ON HEALTH & MEDICINE: The Unforgettable Legacy of Thalidomide 570FOCUS ON HEALTH & MEDICINE: Chiral Drugs 571

Chiral Pain Relievers 572Parkinson’s Disease and l-Dopa 572Fischer Projections 574

Optical Activity 575The Physical Properties of Enantiomers 575Specific Rotation 577

Compounds with Two or More Chirality Centers 578 FOCUS ON THE HUMAN BODY: The Sense of Smell 580Chapter Review 581

Key Terms 581Key Concepts 582Key Skills 582Problems 583Challenge Problems 587Answers to Problems 588

Alessandro0770/Getty Images

Aldehydes and Ketones 590

16.2

16.2A16.2B

16.3

16.4

16.5

16.5A16.5B

16.6

16.6A16.6B16.6C

16.7

16.8

16.8A16.8B16.8C

General Considerations 598Oxidation of Aldehydes 598Reduction of Aldehydes and Ketones 600Specific Features of Carbonyl Reductions 601Examples of Carbonyl Reduction in Organic Synthesis 602FOCUS ON THE HUMAN BODY: Biological Reductions 603FOCUS ON THE HUMAN BODY: The Chemistry of Vision 603 Acetal Formation 605

Acetals and Hemiacetals 606Cyclic Hemiacetals 609Acetal Hydrolysis 612Chapter Review 612

Key Terms 612Key Concepts 613Key Reactions 613Key Skills 614Problems 615Challenge Problems 620Answers to Problems 620

Likit Supasai/Shutterstock

Carboxylic Acids, Esters, and Amides 624

Structure and Bonding 625

Interesting Carboxylic Acids in Consumer Products and Medicines 633FOCUS ON HEALTH & MEDICINE: Skin Care Products 633

FOCUS ON HEALTH & MEDICINE: Aspirin and Anti-Inflammatory Agents 634Interesting Esters and Amides 635

The Acidity of Carboxylic Acids 636

Reaction with Bases 636Carboxylate Anions—Salts of Carboxylic Acids 637How Does Soap Clean Away Dirt? 639

FOCUS ON HEALTH & MEDICINE: Aspirin 641

The Conversion of Carboxylic Acids to Esters and Amides 643

Ester Formation 643Amide Formation 645Hydrolysis of Esters and Amides 646

Ester Hydrolysis 647Amide Hydrolysis 648FOCUS ON HEALTH & MEDICINE: Olestra, a Synthetic Fat 649Synthetic Polymers in Modern Society—Polyamides and Polyesters 651Nylon—A Polyamide 651

Polyesters 653FOCUS ON HEALTH & MEDICINE: Dissolving Sutures 654FOCUS ON THE ENVIRONMENT: Polymer Recycling 655FOCUS ON HEALTH & MEDICINE: Penicillin 655

18.1

18.2

18.2A18.2B18.2C18.2D

18.3

18.4

18.4A18.4B

18.5

18.5A18.5B18.5C

18.6

18.6A18.6B

18.7

18.8

18.8A18.8B18.8C

18.9

18.9A18.9B

18.10

page xvi

Daniel C Smith

Amines and Neurotransmitters 667

Structure and Bonding 668 Nomenclature 671

Primary Amines 671Secondary and Tertiary Amines 671Aromatic Amines 672

Miscellaneous Nomenclature Facts 672Physical Properties 673

FOCUS ON HEALTH & MEDICINE: Caffeine and Nicotine 674Caffeine 674

Nicotine 675Alkaloids—Amines from Plant Sources 676Morphine and Related Alkaloids 676

Quinine 677Atropine 678Amines as Bases 678Reaction of Amines with Acids 678Ammonium Salts 680

FOCUS ON HEALTH & MEDICINE: Ammonium Salts as Useful Drugs 682 Neurotransmitters 683

Norepinephrine and Dopamine 684Serotonin 685

Acetylcholine and Nicotine Addiction 686FOCUS ON HEALTH & MEDICINE: Epinephrine and Related Compounds 687

Derivatives of 2-Phenylethylamine 688Drugs to Treat Asthma 689

FOCUS ON HEALTH & MEDICINE: Histamine and Antihistamines 689

19.5A19.5B

19.6

19.6A19.6B

19.7

19.7A19.7B

Fcafotodigital/iStock/Getty Images

Lipids 699

Introduction to Lipids 700 Fatty Acids 702

Waxes 704 Triacylglycerols—Fats and Oils 706General Features 707

FOCUS ON HEALTH & MEDICINE: Fats and Oils in the Diet 709Hydrolysis of Triacylglycerols 712

FOCUS ON THE HUMAN BODY: Metabolism of Triacylglycerols 713Soap Synthesis 715

Phospholipids 716Phosphoacylglycerols 716Sphingomyelins 718Cell Membranes 720Structure of the Cell Membrane 720Transport Across a Cell Membrane 721FOCUS ON HEALTH & MEDICINE: Cholesterol, the Most Prominent Steroid 722

Steroid Hormones 725 FOCUS ON HEALTH & MEDICINE: Fat-Soluble Vitamins 727

19.11A19.11B

20

20.1

20.2

20.2A20.2B20.2C

20.3

20.3A20.3B20.3C

20.4

20.4A20.4B20.4C

20.5

20.5A20.5B

MaraZe/Shutterstock

Carbohydrates 743

Introduction 744 Monosaccharides 746Fischer Projection Formulas 748Monosaccharides with More Than One Chirality Center 749Common Monosaccharides 751

The Cyclic Forms of Monosaccharides 752The Cyclic Forms of d-Glucose 752

Haworth Projections 754The Cyclic Forms of Fructose, a Ketohexose 756Reduction and Oxidation of Monosaccharides 758Reduction of the Aldehyde Carbonyl Group 758

Oxidation of the Aldehyde Carbonyl Group 759FOCUS ON HEALTH & MEDICINE: Monitoring Glucose Levels 761Disaccharides 762

FOCUS ON HEALTH & MEDICINE: Lactose Intolerance 765FOCUS ON HEALTH & MEDICINE: Sucrose and Artificial Sweeteners 766

20.6A20.6B20.6C20.6D

20.7

20.7A20.7B

21.3

21.4

21.5

21.5A21.5B

21.6

Polysaccharides 768Cellulose 768Starch 769Glycogen 771FOCUS ON HEALTH & MEDICINE: Human Milk Oligosaccharides 772FOCUS ON THE HUMAN BODY: Useful Carbohydrate Derivatives 772Glycosaminoglycans 773

Chitin 774FOCUS ON THE HUMAN BODY: Blood Type 774Chapter Review 776

Key Terms 776Key Concepts 776Key Reactions 777Key Skills 778Problems 779Challenge Problems 783Answers to Problems 783

Daniel C Smith

Amino Acids, Proteins, and Enzymes 787

Introduction 788 Amino Acids 789General Features of Amino Acids 789Stereochemistry of Amino Acids 791Acid–Base Behavior of Amino Acids 792 Peptides 794

FOCUS ON THE HUMAN BODY: Biologically Active Peptides 799Neuropeptides—Enkephalins and Pain Relief 799

Peptide Hormones—Oxytocin and Vasopressin 800Proteins 802

α-Keratins 808Collagen 808Hemoglobin and Myoglobin 809Protein Hydrolysis and Denaturation 810

Protein Hydrolysis 810Protein Denaturation 811Enzymes—Characteristics and Classification 812

Characteristics of Enzymes 812Classification of Enzymes 813Naming Enzymes 816

How Enzymes Work 817

Enzyme Specificity 817Factors That Affect Enzyme Activity 819Allosteric Control 820

Enzyme Inhibitors 821Zymogens 822

FOCUS ON HEALTH & MEDICINE: Using Enzymes to Diagnose and Treat Diseases 823

Enzyme Levels as Diagnostic Tools 823Treating Disease with Drugs That Interact withEnzymes 823Chapter Review 824

22.1

22.1A22.1B

22.11

Rafe Swan/Cultura Creative/Alamy Stock Photo

Nucleic Acids and Protein Synthesis 835

Nucleosides and Nucleotides 836Nucleosides—Joining a Monosaccharide and a Base 836Nucleotides—Joining a Nucleoside with a Phosphate 839Nucleic Acids 841

The DNA Double Helix 844 Replication 847

RNA 848 Transcription 850 The Genetic Code 851 Translation and Protein Synthesis 853 Mutations and Genetic Diseases 856 Recombinant DNA 858

General Principles 859Polymerase Chain Reaction 860FOCUS ON THE HUMAN BODY: DNA Fingerprinting 860The Human Genome Project 862

FOCUS ON HEALTH & MEDICINE: Viruses 862Chapter Review 864

Key Terms 864Key Concepts 865Key Skills 866Problems 866Challenge Problems 871Answers to Problems 872

Luis Alvarez/Getty Images

Metabolism and Energy Production 875

23.2

23.2A23.2B

23.3

23.3A23.3B23.3C

23.4

23.4A23.4B23.4C

23.5

23.5A23.5B

23.6

23.6A23.6B23.6C

23.7

24

Introduction 876

An Overview of Metabolism 877Stage [1]—Digestion 878

Stages [2]–[4] of Catabolism 879ATP and Energy Production 879General Features of ATP Hydrolysis and Formation 880Coupled Reactions in Metabolic Pathways 881

FOCUS ON THE HUMAN BODY: Creatine and Athletic Performance 884Coenzymes in Metabolism 885

Coenzymes NAD+ and NADH 885Coenzymes FAD and FADH2 887Coenzyme A 888

The Citric Acid Cycle 889Overview of the Citric Acid Cycle 889Specific Steps of the Citric Acid Cycle 890The Electron Transport Chain and Oxidative Phosphorylation 893The Electron Transport Chain 894

ATP Synthesis by Oxidative Phosphorylation 895ATP Yield from Oxidative Phosphorylation 896FOCUS ON HEALTH & MEDICINE: Hydrogen Cyanide 896Chapter Review 897

Key Terms 897Key Concepts 898Key Skills 899Problems 900Challenge Problems 902Answers to Problems 903

Daniel C Smith

Carbohydrate, Lipid, and Protein Metabolism 905

24.2

24.3

24.3A24.3B24.3C24.3D

24.4

24.4A24.4B24.4C

24.5

24.6

24.7

24.7A24.7B24.7C

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Introduction 906 Understanding Biochemical Reactions 906 Glycolysis 908

The Steps in Glycolysis 909The Net Result of Glycolysis 912Glycolysis and Other Hexoses 913FOCUS ON HEALTH & MEDICINE: Glycolysis and Cancer Cells 914The Fate of Pyruvate 914

Conversion to Acetyl CoA 914FOCUS ON HEALTH & MEDICINE: Conversion to Lactate 915FOCUS ON HEALTH & MEDICINE: Conversion to Ethanol 916The ATP Yield from Glucose 917

Gluconeogenesis 919 The Catabolism of Triacylglycerols 920Glycerol Catabolism 920

Fatty Acid Catabolism by β-Oxidation 921The Energy Yield from Fatty Acid Oxidation 923Ketone Bodies 924

Amino Acid Metabolism 926Degradation of Amino Acids—The Fate of the Amino Group 926Degradation of Amino Acids—The Fate of the Carbon Skeleton 929Chapter Review 930

Key Terms 930Key Concepts 930Key Skills 931Problems 932Challenge Problems 936Answers to Problems 936

Available online only in McGraw-Hill Connect® and CreateTM

25.1

25.2

25.2A25.2B25.2C

25.3

25.3A25.3B25.3C

25.4

25.5

25.6

25.6A25.6B25.6C

Delivering O2 and Removing CO2 25-8How CO2 Is Transported in the Blood 25-11Buffers in the Body 25-11

The Blood–Brain Barrier 25-13 The Role of the Kidneys 25-14How the Kidneys Filter the Blood 25-15Composition of Urine 25-16

The Kidneys and pH, Fluid Balance, and Electrolyte Concentration 25-16Chapter Review 25-17

Key Terms 25-17Key Concepts 25-18Problems 25-19Answers to Problems 25-21

Appendices

The Elements A-1

Periodic Table of the Elements A-2

Useful Prefixes, Conversion Factors, Physical Constants, and Common Element Colors A-3Useful Mathematical Concepts A-4

Glossary G-1

Index I-1

List of How To’s (Online)

List of Selected Applications (Online)

This textbook is written for students who have an interest in nursing, nutrition, environmental science, food science,and a wide variety of other health-related professions The content of this book is designed for an introductorychemistry course with no chemistry prerequisite, and is suitable for either a two-semester sequence or a one-semestercour se I have f ou nd that by introduci ng one new concept at a ti me, keepi ng t he basi c t hemes i n f ocus, and brea ki ng

down complex problems into small pieces, many students in these chemistry courses acquire a new appreciation ofboth the human body and the larger world around them

The Learning System Used in General, Organic, & Biological Chemistry

Writing Style A concise writing style allows students to focus on learning major concepts and themes of general,

organic, and biological chemistry Relevant materials from everyday life are used to illustrate concepts, and topicsare broken into small chunks of information that are more easily learned

Chapter Outline and Chapter Goals The chapter outline lists the main headings of the chapter to help students

map out the organization of each chapter’s content, and the chapter goals identify the key concepts that studentswill learn

Chapter Review The end-of-chapter summary sections are divided into parts: Key Terms, Key Concepts, Key Equations, Key Reactions, and Key Skills, with structures and examples to illustrate important concepts and

skills

Macro-to-Micro Illustrations Because today’s students are visual learners, and because visualizing

molecular-level representations of macroscopic phenomena is critical to the understanding of any chemistry course, manyillustrations in this text include photos or drawings of everyday objects, paired with their molecular representation,

to help students understand the chemistry behind ordinary occurrences

Problem Solving Sample Problems lead students through the thought process tied to successful problem solving by

employing Analysis and Solution parts Sample Problems are paired with Practice Problems to allow students toapply what they have just learned The Practice Problems are followed by More Practice lists to point students toend-of-chapter Problems that are similar in concept Other Problems within the chapter build on the conceptslearned in the Sample and Practice Problems Students can verify their answers to all Practice Problems and odd-numbered in-chapter and end-of-chapter Problems at the end of each chapter

How To’s Key processes are taught to students in a straightforward and easy-to-understand manner by using

examples and multiple, detailed steps to solving problems

Applications Common applications of chemistry to everyday life are found in margin-placed Health Notes,

Consumer Notes, and Environmental Notes, as well as sections titled “Focus on Health & Medicine,” “Focus on theEnvironment,” and “Focus on the Human Body.”

New To This Edition

General

CHAPTER REVIEW Chapter Review, which replaces Chapter Highlights at the end of each chapter, consists of Key

STUDY TIPS Brief Study Tips have been added to the margins in Chapters 1, 4, 7, 11, 13, and 19 to help students

develop general methods for solving recurrent types of problems, such as those that require a specific equation ordrawing the products of an organic reaction

PHOTOS Over one-half of the chapter-opening photos have been replaced with photos emphasizing relevant material

within the chapter More marginal photos of applications on topics such as glaucoma medications, plant-based burgers,and cannabis have also been added

ART The colors in artwork throughout the text were revised for emphasis, clarity, and consistency.

PROBLEMS Over 150 new problems have been added.

Other New Coverage

Some of the new material added within specific chapters is listed below

Coverage on using a scientific calculator with scientific notation and logarithms has been expanded in Sections1.6B and 9.6B Tables with art that indicates what buttons should be pressed and what calculator displays will beshown are given

Figure 3.7 presents a succinct graphic on how to name different kinds of ionic compounds

Chapter 4 opens by presenting a new current topic, the effect of sunscreens like oxybenzone on the bleaching ofcoral reefs Later in the chapter, a practice problem asks students to determine properties of oxybenzone from itsball-and-stick model Recent research on oxybenzone is also discussed in Section 13.11

In Chapter 5, a new Table 5.4 has been added to summarize reaction types with both general cases and specificexamples More color has been added to both reactions and mathematical equations throughout this chapter tohighlight the key components

The discussion of dialysis and osmosis in Section 8.9 has been edited to emphasize the distinction between theserelated concepts Three new problems on this subject have been added

New material on using PET scans to visualize the brain in Alzheimer’s patients has been added to Section 10.5.New material on anesthetics has been added to Section 11.6

New material on sources of methane in the atmosphere has been added to Section 12.6

The treatment of CFCs in Chapter 14 has been updated to include new compounds used as refrigerants that causeless harm to the ozone layer

Section 17.4B now contains information on prostaglandin analogues that are used in the treatment of glaucoma.Additional material is also added to Section 19.11A

Figure 19.1 now presents data on saturated fats, unsaturated oils, and trans fats in bar graph form for easiervisualization of lipid content

The discussion of the HIV drug amprenavir in Section 21.11 has been updated

The art used in Figures 22.2, 22.3, 22.5, and 22.7 has been updated to provide better clarity on the complexbiochemical processes shown

A brief discussion of COVID-19 has been added to Section 22.11

The art in many of the metabolic pathways in Chapters 23 and 24 has been edited to better illustrate the keyfeatures of the steps in these schemes

Our Commitment to Serving Teachers and Learners

TO THE INSTRUCTOR Writing a chemistry textbook is a colossal task Teaching chemistry for over 30 years at

both a private, liberal arts college and a large state university has given me a unique perspective with which to writethis text I have found that students arrive with vastly different levels of preparation and widely different expectationsfor their college experience As an instructor and now an author, I have tried to channel my love and knowledge ofchemistry into a form that allows this spectrum of students to understand chemical science more clearly, and then seeeveryday phenomena in a new light.

TO THE STUDENT I ho p e t h a t t h is t ext and i ts ancill ary pr ogram will hel p you to bett er underst and and appr eci at e

the world of chemistry My interactions with thousands of students in my long teaching career have profoundlyaffected the way I teach and write about chemistry, so please feel free to email me with any comments or questions at

jgsmith@hawaii.edu

•

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Learning Resources for Instructors and Students

Student Solutions Manual

Each chapter contains the solutions to all in-chapter problems, as well as the solutions to all odd-numbered chapter problems

end-of-Instructor’s Solutions Manual

This supplement contains complete, worked-out solutions for all the end-of-chapter problems in the text It can befound within the Instructor’s Resources on Connect’s online learning center

Presentation Tools

Accessed from your textbook’s Instructor’s Resources, Presentation Tools i s an online di gi tal li br ary contai ning

photos and artwork that can be used to create customized lectures, visually enhanced tests and quizzes, compellingcourse websites, or attractive printed support materials All assets are copyrighted by McGraw-Hill Higher Educationbut can be used by instructors for classroom purposes The visual resources in this collection also include:

PowerPoint Slides: For instructors who prefer to create their lectures from scratch, all illustrations, photos, and

tables are pre-inserted by chapter into PowerPoint slides

Accessible Lecture Outlines: Lecture notes incorporating illustrations have been written for the fifth edition text.

They are provided in PowerPoint format so that you may use these lectures as written or customize them to fit yourlecture