Chemistry For Today: General, Organic, and Biochemistry. ISBN 1133602274, 978-1133602279

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Chemistry for Today: General, Organic, and Biochemistry

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Chemistry for Today: General, Organic, © 2014, 2011 Brooks/Cole, Cengage Learning
and Biochemistry Eighth Edition
ALL RIGHTS RESERVED. No part of this work covered by the copyright herein
Spencer L. Seager, Michael R. Slabaugh may be reproduced, transmitted, stored, or used in any form or by any means
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To our grandchildren:
Nate and Braden Barlow, Megan and Bradley Seager, and Andrew Gardner
Alexander, Annie, Christian, Elyse, Foster, Megan, and Mia Slabaugh, Addison and Hadyn Hansen

Unless otherwise noted all art on this page © Cengage Learning 2014

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
About the Authors

Spencer L. Seager
Spencer L. Seager is a professor of chemistry at Weber State University, where he served
as chemistry department chairman from 1969 until 1993. He teaches general chemistry
at the university and is also active in projects to help improve chemistry and other
science education in local elementary schools. He received his B.S. degree in chemistry
and Ph.D. degree in physical chemistry from the University of Utah. Other interests
include making minor home repairs, reading history of science and technology, listening
to classical music, and walking for exercise.

Michael R. Slabaugh
Michael R. Slabaugh is a senior fellow at Weber State University, where he teaches
the year-long sequence of general chemistry, organic chemistry, and biochemistry. He
received his B.S. degree in chemistry from Purdue University and his Ph.D. degree
in organic chemistry from Iowa State University. His interest in plant alkaloids led to
a year of postdoctoral study in biochemistry at Texas A&M University. His current
professional interests are chemistry education and community involvement in science
activities, particularly the State Science and Engineering Fair in Utah. He also enjoys
the company of family, hiking in the mountains, and fishing the local streams.

iv   About the Authors Unless otherwise noted all art on this page © Cengage Learning 2014

Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
About the Cover

Dr. Melina B. Jampolis, M.D. is an internist and board-certified Physician Nutrition


Specialist (one of only several hundred in the country). She specializes exclusively in
nutrition for weight loss and disease prevention and treatment.
A graduate of Tufts University as well as Tufts School of Medicine, she completed
her residency in internal medicine at Santa Clara Valley Medical Center, a Stanford
University teaching hospital. In 2005, Dr. Jampolis hosted a program on the Discovery
Network’s FIT TV titled Fit TV’s Diet Doctor, and she currently serves as the diet and
fitness expert for CNNHealth.com. She serves as a member of the medical advisory
board of Better Homes and Gardens and VivMag.com.
Her first book, The No-Time-to-Lose Diet, was released in January 2007, and the
paperback version, The Busy Person’s Guide to Permanent Weight Loss, was released in
May 2008. Her latest book, The Calendar Diet, was released in March 2012.
Dr. Jampolis lectures throughout the country on nutrition for weight loss and optimal
health. She has been interviewed on nutrition and weight loss–related topics by USA
Today, USA Weekend, New York Post, The Washington Post, Family Circle, Better Homes
and Gardens, Glamour.com, Ladies’ Home Journal, First for Women, Women’s World,
Alternative Medicine, Women’s Health, SanFrancisco Magazine, Clean Eating, Baby
Talk, and more. She has appeared numerous times on Live with Regis & Kelly, CNN,
FOX News Channel, FOX Business Network, as well as on The Dr. Oz Show, Dr. Drew’s
Lifechangers, and local television and radio stations, including ABC, NBC, FOX, KGO
radio, and KRON-4 news.
Dr. Jampolis lives in Los Angeles with her husband and two-year-old son. She
maintains a small private practice in San Francisco and Los Angeles.

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Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
DR. MELINA B. JAMPOLIS, M.D.
About the Cover
Ask an Expert
Q: Do foods, medications, and supplements interact?

A: Most people are aware that medications can interact with one another, but

© Michael Roud Photography


many may not be aware of the interaction of certain foods and supplements with
medications. These interactions generally result from either impaired absorption or
altered metabolism.
   Iron, present in food and supplements, has numerous clinically relevant interac-
Dr. Melina B. Jampolis, M.D. tions. Absorption of heme iron from meat protein is very efficient and differs from the
is a Los Angeles, California,
Physician Nutrition absorption of non-heme iron such as that found in plant foods and supplements. Non-
Specialist—a specialty heme iron must be digested and converted to a soluble and ionized form in order to
practiced by only a few
be absorbed in the intestine. This process is enhanced by gastric acid which improves
hundred physicians in the
United States. She focuses the solubility of iron and reduces it to ferrous iron (2 + oxidation state) for better ab-
exclusively on nutrition for sorption. Acid reducing medications such as proton pump inhibitors and antacids re-
weight loss and disease
duce the absorption of non-heme iron by decreasing the acidity in the stomach and
prevention and treatment.
upper duodenum. Tannins found in tea and phytates found in legumes and wheat
bran may also impair iron absorption by chelating iron, preventing its absorption.
Ascorbic acid (vitamin C) enhances absorption by reducing ferric to ferrous iron and chelating ferrous iron, improving its
absorption at the higher pH of the regions of the small intestine located farthest from the stomach. Calcium supplements
and dairy foods also impair iron absorption. Ferrous iron can also interact with several types of medications including
the antibiotics ciprofloxacin and tetracycline, and thyroid medication. It impairs their absorption and thereby potentially
reduces their effectiveness as medications.
Calcium, also found in both dairy foods and some supplements, has several food and drug interactions. Like iron,
calcium is only absorbed in ionic form. It too requires an acidic environment for optimal absorption, particularly when
it is in the calcium carbonate form. This form is best taken with meals. Unlike iron, more calcium is absorbed in the
parts of the small intestine located farthest from the acidic stomach. As a result, acid blocking medications are not as
detrimental to absorption as they are for iron.
But calcium citrate, which is more soluble at a neutral pH, may still be the preferable form for those with compro-
mised levels of stomach acid. Phytates and oxalic acid, found in spinach, rhubarb, collard greens, sweet potatoes and
beans bind calcium, creating insoluble complexes that cannot be absorbed. Calcium can also decrease the absorption
of several medications including quinolone antibiotics, tetracycline, and thyroid replacement medication.
Unlike iron and calcium which interact with medications by preventing their absorption, grapefruit interacts with numer-
ous medications through its effect on drug metabolism. A flavonoid compound in grapefruit inhibits an enzyme, cytochrome
P450 3A4, that is important for the degradation of numerous drugs. Since less of the drug is broken down when consumed
with grapefruit or grapefruit juice, more of the drug is bioavailable, which can potentially lead to toxic levels in some cases. In
addition to several of the cholesterol reducing statin medications, other drugs affected this way include several blood pres-
sure lowering medications, the anti-retroviral medication saquinavir, and the immunosuppressive medication cyclosporine.
St. John’s wort, a popular herbal supplement often used for the treatment of mild depression, may enhance rather
than suppress the cytochrome P450 34A system in a clinically relevant manner, potentially reducing the effectiveness of
several HIV medications, immunosuppressive medications, and even cancer treatment drugs.
There are numerous other food, drug and supplement interactions. While not all of them may be clinically relevant, their
presence underscore the importance of discussing both supplementation and diet with appropriate health care provider.
This is especially true if you are taking prescription medication or supplements to treat a deficiency or medical condition.

vi   About the Cover Unless otherwise noted all art on this page © Cengage Learning 2014

Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
B r i e f C o n te n t s

Chapter 1 Chapter 13
Matter, Measurements, and Alcohols, Phenols, and Ethers 432
Calculations   2
Chapter 14
Chapter 2 Aldehydes and Ketones 466
Atoms and Molecules   46
Chapter 15
Chapter 3 Carboxylic Acids and Esters 496
Electronic Structure and the
Periodic Law   72 Chapter 16
Amines and Amides 526
Chapter 4
Forces Between Particles   102 Chapter 17
Carbohydrates 558
Chapter 5
Chemical Reactions   146 Chapter 18
Lipids 592
Chapter 6
The States of Matter   176 Chapter 19
Proteins 622
Chapter 7
Solutions and Colloids   214 Chapter 20
Enzymes 654
Chapter 8
Reaction Rates and Equilibrium   254 Chapter 21
Nucleic Acids and Protein Synthesis 680
Chapter 9
Acids, Bases, and Salts   282 Chapter 22
Nutrition and Energy for Life 716
Chapter 10
Radioactivity and Nuclear Processes   328 Chapter 23
Carbohydrate Metabolism 746
Chapter 11
Organic Compounds: Alkanes   360 Chapter 24
Lipid and Amino Acid Metabolism 774
Chapter 12
Unsaturated Hydrocarbons   398 Chapter 25
Body Fluids 802

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
C o n te n t s
Chapter 1 2.6 Avogadro’s Number: The Mole   57
Matter, Measurements, and 2.7 The Mole and Chemical Formulas   62
Concept Summary   65
Calculations 2
Key Terms and Concepts   65
1.1 What Is Matter?   4
Exercises   66
1.2 Properties and Changes   5
Additional Exercises   69
1.3 A Model of Matter   8
Allied Health Exam Connection   69
1.4 Classifying Matter   10
Chemistry for Thought   70
1.5 Measurement Units   13 Case Study 46
1.6 The Metric System   14 Chemistry Around Us 2.1 Looking at Atoms 51
1.7 Large and Small Numbers   19 at the counter 2.1 Nonprescription
1.8 Significant Figures   22 Medicines 53
1.9 Using Units in Calculations   27 Chemistry and your health 2.1 Are You at
1.10 Calculating Percentages   29 Risk for Osteoporosis? 54
Study Skills 2.1 Help with Mole Calculations 63
1.11 Density   30
Case Study Follow-up 64
Concept Summary   35
Key Terms and Concepts   37
Key Equations   37
Chapter 3
Exercises   37
Additional Exercises   43 Electronic Structure and
Allied Health Exam Connection   44 the Periodic Law 72
Chemistry for Thought   45
3.1 The Periodic Law and Table   74
Case Study 2
3.2 Electronic Arrangements in Atoms   75
Chemistry Around Us 1.1 A Central Science 5
3.3 The Shell Model and Chemical Properties   79
Chemistry Around Us 1.2 Cosmetics: Complex
Mixtures and Complex Regulations 6 3.4 Electronic Configurations   81
Chemistry Around Us 1.3 Effects of 3.5 Another Look at the Periodic Table   85
Temperature on Body Function 19 3.6 Property Trends within the Periodic Table   90
Study Skills 1.1 Help with Calculations 30 Concept Summary   96
Chemistry and Your Health 1.1 Health Key Terms and Concepts   96
Information on the Web 32
Exercises   97
Ask an Expert 1.1  Does food density matter when
Additional Exercises   99
you’re trying to lose weight?   34
Case Study Follow-up 35 Allied Health Exam Connection   99
Chemistry for Thought   101
Case Study 72
Chapter 2
Ask an Expert 3.1  Are calcium supplements
Atoms and Molecules 46 necessary?   76
Chemistry Around Us 3.1 Nano World 84
2.1 Symbols and Formulas   47
Study Skills 3.1 The Convention Hotels
2.2 Inside the Atom   50 Analogy 88
2.3 Isotopes   51 Chemistry and Your Health 3.1 Iron: Too
2.4 Relative Masses of Atoms and Molecules   52 Much of a Good Thing? 90
2.5 Isotopes and Atomic Weights   56 Case Study Follow-up 95

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Chapter 4 5.11 Reaction Yields   165
Concept Summary   168
Forces Between Particles 102 Key Terms and Concepts   169
4.1 Noble Gas Configurations   103 Key Equations   169
4.2 Ionic Bonding   106 Exercises   169
4.3 Ionic Compounds   108 Additional Exercises   173
4.4 Naming Binary Ionic Compounds   110 Allied Health Exam Connection   173
4.5 The Smallest Unit of Ionic Compounds   112 Chemistry for Thought   175
4.6 Covalent Bonding   114 Case Study 146
4.7 Polyatomic Ions   118 At the Counter 5.1 Antiseptics and
Disinfectants 153
4.8 Shapes of Molecules and Polyatomic Ions   120
Chemistry and Your Health 5.1 The
4.9 The Polarity of Covalent Molecules   124
Importance of Color in Your Diet 158
4.10 More about Naming Compounds   128 Chemistry Around Us 5.1 Redox Reactions and
4.11 Other Interparticle Forces   131 Energy for Life 161
Concept Summary   137 Chemistry Around Us 5.2 Air Bag
Key Terms and Concepts   138 Chemistry 165
Exercises   139 Study Skills 5.1 Help with Oxidation
Numbers 166
Additional Exercises   143
Case Study Follow-up 167
Allied Health Exam Connection   143
Chemistry for Thought   145
Case Study 102 Chapter 6
Chemistry and your health 4.1 Fight
Hypertension with Potassium 109 The States of Matter 176
Chemistry Around Us 4.1 Water: One of Earth’s 6.1 Observed Properties of Matter   178
Special Compounds 115 6.2 The Kinetic Molecular Theory of Matter   180
At the Counter 4.1 Versatile Zinc Oxide   125
6.3 The Solid State   181
Study Skills 4.1 Help with Polar and Nonpolar
6.4 The Liquid State   182
Molecules 130
6.5 The Gaseous State   183
Chemistry Around Us 4.2 Rare Earths Are All
Around You 133 6.6 The Gas Laws   183
Case Study Follow-up 137 6.7 Pressure, Temperature, and Volume
Relationships   187
6.8 The Ideal Gas Law   191
Chapter 5
6.9 Dalton’s Law   193
Chemical Reactions 146 6.10 Graham’s Law   194
5.1 Chemical Equations   147 6.11 Changes in State   195
5.2 Types of Reactions   149 6.12 Evaporation and Vapor Pressure   195
5.3 Redox Reactions   150 6.13 Boiling and the Boiling Point   197
5.4 Decomposition Reactions   154 6.14 Sublimation and Melting   198
5.5 Combination Reactions   155 6.15 Energy and the States of Matter   199
5.6 Replacement Reactions   155 Concept Summary   204
5.7 Ionic Equations   157 Key Terms and Concepts   205
5.8 Energy and Reactions   160 Key Equations   206
5.9 The Mole and Chemical Equations   160 Exercises   206
5.10 The Limiting Reactant   163 Additional Exercises   210

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Allied Health Exam Connection   210 Chapter 8
Chemistry for Thought   212
Case Study 176 Reaction Rates and Equilibrium 254
Chemistry and Your Health 6.1 Huffing: 8.1 Spontaneous and Nonspontaneous
A Potential Introduction of Children to Drug Processes   256
Abuse 186
8.2 Reaction Rates   257
At the Counter 6.1 Cutting Drug Costs with
8.3 Molecular Collisions   258
Generics 190
Chemistry Around Us 6.1 Blood Pressure: A
8.4 Energy Diagrams   261
Barometer of Health 197 8.5 Factors That Influence Reaction Rates   262
Chemistry Around Us 6.2 Therapeutic Uses of 8.6 Chemical Equilibrium   264
Oxygen Gas 200 8.7 The Position of Equilibrium   266
Study Skills 6.1 Which Gas Law to Use 202 8.8 Factors That Influence Equilibrium
Case Study Follow-up 203 Position   268
Concept Summary   273
Key Terms and Concepts   274
Chapter 7 Key Equations   274
Exercises   274
Solutions and Colloids 214
Additional Exercises   278
7.1 Physical States of Solutions   215
Allied Health Exam Connection   279
7.2 Solubility   217
Chemistry for Thought   280
7.3 The Solution Process   220 Case Study 254
7.4 Solution Concentrations   224 At the Counter 8.1 Time-Release
7.5 Solution Preparation   228 Medications 259
7.6 Solution Stoichiometry   232 Chemistry and Your Health 8.1 Hypothermia:
7.7 Solution Properties   234 Surviving the Big Chill 265
Chemistry Around Us 8.1 The True Value of
7.8 Colloids   239
Platinum and Gold 269
7.9 Dialysis   242
Study Skills 8.1 Le Châtelier’s Principle in
Concept Summary   244 Everyday Life 272
Key Terms and Concepts   245 Case Study Follow-up 272
Key Equations   246
Exercises   246
Additional Exercises   251
Allied Health Exam Connection   251
Chapter 9
Chemistry for Thought   253 Acids, Bases, and Salts 282
Case Study 214
9.1 The Arrhenius Theory   283
At the Counter 7.1 Oral Rehydration
9.2 The Brønsted Theory   284
Therapy 225
Chemistry and Your Health 7.1 The
9.3 Naming Acids   285
Risk of Dehydration During Vigorous Youth 9.4 The Self-Ionization of Water   287
Activities 227 9.5 The pH Concept   289
Study Skills 7.1 Getting Started with Molarity 9.6 Properties of Acids   292
Calculations 238
9.7 Properties of Bases   296
Chemistry Around Us 7.1 Tears: Solutions for
9.8 Salts   297
Many Eye Problems 241
Chemistry Around Us 7.2 Global Warming and
9.9 The Strengths of Acids and Bases   300
a Cooler Europe 243 9.10 Analyzing Acids and Bases   307
Case Study Follow-up 244 9.11 Titration Calculations   309

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
9.12 Hydrolysis Reactions of Salts   310 At the Counter 10.1 The Do’s and Don’ts of
9.13 Buffers   312 Buying Prescription Drugs Online 352
Case Study Follow-up 353
Concept Summary   317
Key Terms and Concepts   318
Key Equations   318 Chapter 11
Exercises   319
Organic Compounds: Alkanes 360
Additional Exercises   326
11.1 Carbon: The Element of Organic Compounds   361
Allied Health Exam Connection   326
11.2 Organic and Inorganic Compounds Compared   363
Chemistry for Thought   327
Case Study 282
11.3 Bonding Characteristics and Isomerism   364
Chemistry Around Us 9.1 Carbon Dioxide in 11.4 Functional Groups: The Organization
the Oceans 301 of Organic Chemistry   367
Study Skills 9.1 Writing Reactions of 11.5 Alkane Structures   369
Acids 305 11.6 Conformations of Alkanes   373
Chemistry and Your Health 9.1 Do You Have 11.7 Alkane Nomenclature   375
Acid Reflux Disease? 306 11.8 Cycloalkanes   381
Ask an Expert 9.1  Does diet play a role in peptic
11.9 The Shape of Cycloalkanes   383
ulcer disease?   315
11.10 Physical Properties of Alkanes   386
Case Study Follow-up 316
11.11 Alkane Reactions   388
Concept Summary   390
Chapter 10 Key Terms and Concepts   391
Radioactivity and Key Equations   391
Exercises   391
Nuclear Processes 328
Additional Exercises   396
10.1 Radioactive Nuclei   329 Allied Health Exam Connection   396
10.2 Equations for Nuclear Reactions   331 Chemistry for Thought   397
10.3 Isotope Half-Life   334 Case Study 360
10.4 The Health Effects of Radiation   336 Study Skills 11.1 Changing Gears for Organic
10.5 Measurement Units for Radiation   338 Chemistry 364
10.6 Medical Uses of Radioisotopes   341 Ask an Expert 11.1  Is organic food worth the
10.7 Nonmedical Uses of Radioisotopes   342 price?   370
Chemistry Around Us 11.1 Oil Production:
10.8 Induced Nuclear Reactions   344
From Wells and Sands 384
10.9 Nuclear Energy   347
Chemistry and Your Health 11.1 Skin
Concept Summary   353 Moisturizers: Choosing One That Works 386
Key Terms and Concepts   354 Chemistry Around Us 11.2 Ice Storms and
Key Equations   355 Deadly Carbon Monoxide 388
Exercises   355 Case Study Follow-up 389

Additional Exercises   357


Allied Health Exam Connection   357
Chapter 12
Chemistry for Thought   359
Case Study 328 Unsaturated Hydrocarbons 398
Chemistry Around Us 10.1 Radiation Exposure 12.1 The Nomenclature of Alkenes   400
in Modern Life 339
12.2 The Geometry of Alkenes   403
Chemistry Around Us 10.2 Radon: A
Chemically Inert Health Risk 343 12.3 Properties of Alkenes   407
Chemistry and Your Health 10.1 Is Irradiated 12.4 Addition Polymers   412
Food Safe? 350 12.5 Alkynes   415

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
12.6 Aromatic Compounds and the Benzene Structure   416 HOW REACTIONS OCCUR 13.1 The Dehydration of
12.7 The Nomenclature of Benzene Derivatives   419 an Alcohol 441
Study Skills 13.1 A Reaction Map for
12.8 Properties and Uses of Aromatic Compounds   423
Alcohols 446
Concept Summary   425
Chemistry Around Us 13.1 Alcohol and
Key Terms and Concepts   426 Antidepressants Don’t Mix 447
Key Reactions   426 Ask an Expert 13.1  What are polyphenols?   449
Exercises   426 Chemistry and Your Health 13.1 Why Do Teens
Additional Exercises   431 Drink? 451
Allied Health Exam Connection   431 Chemistry Around Us 13.2 General Anesthetics 454

Chemistry for Thought   431 Case Study Follow-up 457

Case Study 398


Chemistry Around Us 12.1 Watermelon: Chapter 14
A Source of Lycopene 402
Chemistry Around Us 12.2 Seeing the Light 405 Aldehydes and Ketones 466
Study Skills 12.1 Keeping a Reaction Card
14.1 The Nomenclature of Aldehydes and
File 411 Ketones   468
Study Skills 12.2 A Reaction Map for Alkenes 413
14.2 Physical Properties   471
HOW REACTIONS OCCUR 12.1 The Hydration of
14.3 Chemical Properties   473
Alkenes: An Addition Reaction 417
Chemistry and Your Health 12.1 Beautiful,
14.4 Important Aldehydes and Ketones   485
Brown ... and Overdone 420 Concept Summary   488
At the Counter 12.1 Smoking: It’s Quitting Key Terms and Concepts   488
Time 422 Key Reactions   489
Case Study Follow-up 424 Exercises   490
Additional Exercises   494
Chapter 13 Allied Health Exam Connection   495
Alcohols, Phenols, Chemistry for Thought   495
Case Study 466
and Ethers 432 Chemistry Around Us 14.1 Faking a Tan 472
13.1 The Nomenclature of Alcohols and Phenols   434 At the Counter 14.1 Birth Control: Progesterone
13.2 Classification of Alcohols   437 Substitutes 475
13.3 Physical Properties of Alcohols   437 How Reactions Occur 14.1 Hemiacetal
Formation 480
13.4 Reactions of Alcohols   439
Study Skills 14.1 A Reaction Map for Aldehydes
13.5 Important Alcohols   444 and Ketones 481
13.6 Characteristics and Uses of Phenols   448 Chemistry Around Us 14.2 Vanilloids: Hot
13.7 Ethers   451 Relief from Pain 483
13.8 Properties of Ethers   452 Chemistry and Your Health 14.1 Vitamin A
13.9 Thiols   453 and Birth Defects 485
Case Study Follow-up 487
13.10 Polyfunctional Compounds   455
Concept Summary   457
Key Terms and Concepts   458 Chapter 15
Key Reactions   459
Carboxylic Acids
Exercises   460
Additional Exercises   464
and Esters 496
Allied Health Exam Connection   464 15.1 The Nomenclature of Carboxylic Acids   498
Chemistry for Thought   464 15.2 Physical Properties of Carboxylic Acids   499
Case Study 432 15.3 The Acidity of Carboxylic Acids   502

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
15.4 Salts of Carboxylic Acids   504 Chemistry Around Us 16.1 Aspirin
15.5 Carboxylic Esters   506 Substitutes 538
Study Skills 16.1 A Reaction Map for Amines 541
15.6 The Nomenclature of Esters   510
Chemistry and Your Health 16.1 Energy
15.7 Reactions of Esters   511
Drinks: Are They Really Harmless as a Source of
15.8 Esters of Inorganic Acids   515 Energy? 544
Concept Summary   518 Case Study Follow-up 550
Key Terms and Concepts   519
Key Reactions   519
Chapter 17
Exercises   520
Additional Exercises   524 Carbohydrates 558
Allied Health Exam Connection   524 17.1 Classes of Carbohydrates   560
Chemistry for Thought   524 17.2 The Stereochemistry of Carbohydrates   561
Case Study 496 17.3 Fischer Projections   565
At the Counter 15.1 Alpha Hydroxy Acids in 17.4 Monosaccharides   569
Cosmetics 501
17.5 Properties of Monosaccharides   570
Chemistry and Your Health 15.1 Aspirin:
Should You Take a Daily Dose? 512 17.6 Important Monosaccharides   576
Study Skills 15.1 A Reaction Map for Carboxylic 17.7 Disaccharides   577
Acids 514 17.8 Polysaccharides   580
How Reactions Occur 15.1 Ester Concept Summary   586
Saponification 514 Key Terms and Concepts   587
Chemistry Around Us 15.1 Nitroglycerin in
Key Reactions   587
Dynamite and in Medicine 517
Exercises   588
Case Study Follow-up 517
Additional Exercises   591
Allied Health Exam Connection   591
Chapter 16 Chemistry for Thought   591
Amines and Amides 526 Case Study 558
Chemistry Around Us 17.1 Sugar-Free Foods
16.1 Classification of Amines   528 and Diabetes 574
16.2 The Nomenclature of Amines   528 Study Skills 17.1 Biomolecules: A New Focus 578
16.3 Physical Properties of Amines   531 Chemistry and Your Health 17.1 Potato
16.4 Chemical Properties of Amines   532 Comeback: The Healthy Side of Spuds 579
16.5 Amines as Neurotransmitters   539 Ask an Expert 17.1  Is high-fructose corn syrup
16.6 Other Biologically Important Amines   542 worse for your health than table sugar?   584
Case Study Follow-up 586
16.7 The Nomenclature of Amides   545
16.8 Physical Properties of Amides   546
16.9 Chemical Properties of Amides   547 Chapter 18
Concept Summary   550 Lipids 592
Key Terms and Concepts   551
18.1 Classification of Lipids   594
Key Reactions   552
18.2 Fatty Acids   594
Exercises   552
18.3 The Structure of Fats and Oils   597
Additional Exercises   556
18.4 Chemical Properties of Fats and Oils   599
Allied Health Exam Connection   556
18.5 Waxes   602
Chemistry for Thought   556
18.6 Phosphoglycerides   602
Case Study 526
Ask an Expert 16.1  Does caffeine help with
18.7 Sphingolipids   605
weight loss?   530 18.8 Biological Membranes   606

xiv   Contents Unless otherwise noted all art on this page © Cengage Learning 2014

Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
18.9 Steroids   608 Chemistry Around Us 19.1 Alzheimer’s
18.10 Steroid Hormones   612 Disease 636
Chemistry Around Us 19.2 Sickle-Cell
18.11 Prostaglandins   614
Disease 641
Concept Summary   616
Study Skills 19.1 Visualizing Protein
Key Terms and Concepts   617 Structure 643
Key Reactions   617 Case Study Follow-up 647
Exercises   618
Additional Exercises   619
Allied Health Exam Connection   620
Chapter 20
Chemistry for Thought   621 Enzymes 654
Case Study 592
20.1 General Characteristics of Enzymes   655
Study Skills 18.1 A Reaction Map for Triglycerides 602
20.2 Enzyme Nomenclature and Classification   657
Chemistry and Your Health 18.1 Performance
Enhancing Steroids 603 20.3 Enzyme Cofactors   659
Chemistry Around Us 18.1 Algae in Your Fuel 20.4 The Mechanism of Enzyme Action   661
Tank 609 20.5 Enzyme Activity   662
Ask an Expert  How significantly can diet really 20.6 Factors Affecting Enzyme Activity   663
lower cholesterol?   610 20.7 Enzyme Inhibition   664
Chemistry Around Us 18.2 Olive Oil: A Heart-
20.8 The Regulation of Enzyme Activity   670
Healthy Lipid 614
20.9 Medical Application of Enzymes   673
Case Study Follow-up 615
Concept Summary   675
Key Terms and Concepts   676
Chapter 19 Key Reactions   676
Proteins 622 Exercises   677
Additional Exercises   678
19.1 The Amino Acids   623
Allied Health Exam Connection   678
19.2 Zwitterions   626
Chemistry for Thought   679
19.3 Reactions of Amino Acids   628
Case Study 654
19.4 Important Peptides   631
Chemistry and Your Health 20.1 Enzymes
19.5 Characteristics of Proteins   633 and Disease 658
19.6 The Primary Structure of Proteins   637 At the Counter 20.1 ACE Inhibitors
19.7 The Secondary Structure of Proteins   638 (Angiotensin-Converting Enzyme Inhibitors) 660
19.8 The Tertiary Structure of Proteins   641 Chemistry Around Us 20.1 Enzyme Discovery
19.9 The Quaternary Structure of Proteins   643 Heats Up 665
Chemistry Around Us 20.2 Avoiding Mercury
19.10 Protein Hydrolysis and Denaturation   645
in Fish 667
Concept Summary   647
Study Skills 20.1 A Summary Chart of Enzyme
Key Terms and Concepts   648 Inhibitors 672
Key Reactions   649 Case Study Follow-up 675
Exercises   650
Additional Exercises   652
Chapter 21
Allied Health Exam Connection   652
Chemistry for Thought   652 Nucleic Acids and Protein
Case Study 622 Synthesis 680
Ask an Expert 19.1  Can a higher protein diet help
me lose weight?   629 21.1 Components of Nucleic Acids   682
Chemistry and Your Health 19.1 C-Reactive 21.2 The Structure of DNA   684
Protein: A Message from the Heart 632 21.3 DNA Replication   688

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
21.4 Ribonucleic Acid (RNA)   692 Chemistry for Thought   745
21.5 The Flow of Genetic Information   696 Case Study 716
21.6 Transcription: RNA Synthesis   697 Chemistry Around Us 22.1 The Ten Most
Dangerous Foods to Eat While Driving 724
21.7 The Genetic Code   699
Chemistry and Your Health 22.1 Vitamin
21.8 Translation and Protein Synthesis   702
Water: Beneficial or Not? 725
21.9 Mutations   705 Study Skills 22.1 Bioprocesses 732
21.10 Recombinant DNA   705 Chemistry Around Us 22.2 Calorie
Concept Summary   710 Language 733
Key Terms and Concepts   712 Ask an Expert 22.1  Is it better to take a fiber
Exercises   712 supplement or to eat fiber-fortified foods?   739
Case Study Follow-up 740
Additional Exercises   714
Allied Health Exam Connection   714
Chemistry for Thought   714
Case Study 680 Chapter 23
At the Counter 21.1 Nucleic Acid
Supplements 688 Carbohydrate Metabolism 746
Chemistry Around Us 21.1 The Clone Wars 693 23.1 The Digestion of Carbohydrates   747
Chemistry Around Us 21.2 Is There a DNA 23.2 Blood Glucose   748
Checkup in Your Future? 699 23.3 Glycolysis   748
Study Skills 21.1 Remembering Key Words 701
23.4 The Fates of Pyruvate   752
Chemistry Around Us 21.3 Stem Cell
23.5 The Citric Acid Cycle   754
Research 703
23.6 The Electron Transport Chain   757
Chemistry Around Us 21.4 DNA and the
Crime Scene   707 23.7 Oxidative Phosphorylation   757
Chemistry and Your Health 21.1 Genetically 23.8 The Complete Oxidation of Glucose   759
Modified Foods 709 23.9 Glycogen Metabolism   761
Case Study Follow-up 710 23.10 Gluconeogenesis   762
23.11 The Hormonal Control of
Chapter 22 Carbohydrate Metabolism   765
Concept Summary   767
Nutrition and Energy for Life 716 Key Terms and Concepts   769
22.1 Nutritional Requirements   717 Key Reactions   769
22.2 The Macronutrients   719 Exercises   770
22.3 Micronutrients I: Vitamins   722 Additional Exercises   772
22.4 Micronutrients II: Minerals   725 Allied Health Exam Connection   772
22.5 The Flow of Energy in the Biosphere   726 Chemistry for Thought   773
22.6 Metabolism and an Overview Case Study 746
of Energy Production   729 Ask an Expert 23.1  How can we avoid energy
22.7 ATP: The Primary Energy Carrier   730 crashes?   750
Chemistry Around Us 23.1 Lactate
22.8 Important Coenzymes in the Common Catabolic
Accumulation 756
Pathway   735
Study Skills 23.1 Key Numbers for ATP
Concept Summary   741
Calculations 762
Key Terms and Concepts   742
Chemistry Around Us 23.2 What Is the Best
Key Reactions   742 Weight-Loss Strategy? 764
Exercises   743 Chemistry and Your Health 23.1 Reactive
Additional Exercises   744 Hypoglycemia: What Causes It? 766
Allied Health Exam Connection   744 Case Study Follow-up 767

xvi   Contents Unless otherwise noted all art on this page © Cengage Learning 2014

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Chapter 24 Chapter 25
Lipid and Amino Acid Body Fluids 802
Metabolism 774 25.1 A Comparison of Body Fluids   803
24.1 Blood Lipids   776 25.2 Oxygen and Carbon Dioxide Transport   804
24.2 Fat Mobilization   779 25.3 Chemical Transport to the Cells   809
24.3 Glycerol Metabolism   780 25.4 The Constituents of Urine   810
24.4 The Oxidation of Fatty Acids   780 25.5 Fluid and Electrolyte Balance   810
24.5 The Energy from Fatty Acids   783 25.6 Acid–Base Balance   812
24.6 Ketone Bodies   784 25.7 Buffer Control of Blood pH   813
24.7 Fatty Acid Synthesis   786 25.8 Respiratory Control of Blood pH   813
24.8 Amino Acid Metabolism   787 25.9 Urinary Control of Blood pH   814
24.9 Amino Acid Catabolism: The Fate of the Nitrogen 25.10 Acidosis and Alkalosis   815
Atoms   788 Concept Summary   818
24.10 Amino Acid Catabolism: The Fate of the Carbon Key Terms and Concepts   819
Skeleton   792 Key Reactions   819
24.11 Amino Acid Biosynthesis   795 Exercises   819
Concept Summary   797 Additional Exercises   821
Key Terms and Concepts   798 Allied Health Exam Connection   821
Key Reactions   798 Chemistry for Thought   821
Exercises   799 Case Study 802
Additional Exercises   801 At the Counter 25.1 Erythropoietin: A
Allied Health Exam Connection   801 Performance-enhancing Drug 806
Chemistry for Thought   801 Chemistry and Your Health 25.1 Exercise
Beats Angioplasty 807
Case Study 774
Chemistry Around Us 25.1 Pulse
Ask an Expert 24.1  Are certain foods better for
Oximetry 812
the brain?   778
Case Study Follow-up 817
Study Skills 24.1 Key Numbers for ATP
Calculations 785
Chemistry and Your Health 24.1 Omega-3
Fatty Acids: Will They Improve Heart Appendix A The International System
Health? 790 of Measurements   A-1
Chemistry Around Us 24.1 Phenylketonuria Appendix B Answers to Even-Numbered
(PKU) 793 End-of-Chapter Exercises   B-1
Chemistry Around Us 24.2 Phenylalanine and Appendix C Solutions to Learning Checks   C-1
Diet Foods 794
Case Study Follow-up 796

Glossary G-1
Index I-1

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
P r e f ace

The Image of Chemistry


We, as authors, are pleased that the acceptance of the previous seven editions of this text-
book by students and their teachers has made it possible to publish this eighth edition. In
the earlier editions, we expressed our concern about the negative image of chemistry held
by many of our students, and their genuine fear of working with chemicals in the labora-
tory. Unfortunately, this negative image not only persists, but seems to be intensifying.
Reports in the media related to chemicals or to chemistry continue to be primarily nega-
tive, and in many cases seem to be designed to increase the fear and concern of the general
public. With this edition, we continue to hope that those who use this book will gain a
more positive understanding and appreciation of the important contributions that chemis-
try makes in their lives.

Theme and Organization


This edition continues the theme of the positive and useful contributions made by
­chemistry in our world.
This text is designed to be used in either a two-semester or three-quarter course of study
that provides an introduction to general chemistry, organic chemistry, and biochemistry.
Most students who take such courses are majoring in nursing, other health professions, or
the life sciences, and consider biochemistry to be the most relevant part of the course of
study. However, an understanding of biochemistry depends upon a sound background in
organic chemistry, which in turn depends upon a good foundation in general chemistry.
We have attempted to present the general and organic chemistry in sufficient depth and
breadth to make the biochemistry understandable.
As with previous editions, this textbook is published in a complete hardcover form and
a two-volume paperback edition. One volume of the paperback edition contains all the
general chemistry and the first two chapters of organic chemistry from the hardcover text.
The second volume of the paperback edition contains all the organic chemistry and bio-
chemistry of the hardcover edition. The availability of the textbook in these various forms
has been a very popular feature among those who use the text because of the flexibility it
affords them.
The decisions about what to include and what to omit from the text were based on our
combined 75-plus years of teaching, input from numerous reviewers and adopters, and
our philosophy that a textbook functions as a personal tutor to each student. In the role
of a personal tutor, a text must be more than just a collection of facts, data, and exercises.
It should also help students relate to the material they are studying, carefully guide them
through more difficult material, provide them with interesting and relevant examples of
chemistry in their lives, and become a reference and a resource that they can use in other
courses or their professions.

Unless otherwise noted all art on this page © Cengage Learning 2014 Preface xix

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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
New to This Edition
In this eighth edition of the text, we have some exciting new features, including Case Studies,
which begin each chapter, and Ask an Expert boxes written by CNN health expert Dr. Melina
B. Jampolis. We have also retained features that received a positive reception from our own
students, the students of other adopters, other teachers, and reviewers. The ­retained features
are 23 Study Skills boxes that include 5 reaction maps; 4 How ­Reactions ­Occur boxes; 45
Chemistry Around Us boxes, including 14 new to this edition. The 13 At The ­Counter boxes
reflect coverage of both prescription and non-prescription health-­related products. There are
25 Chemistry and Your Health boxes, with 5 new to this ­edition. A greatly expanded feature
of this eighth edition is the ­Allied Health Exam Connection that follows the exercises at the
end of each chapter. This feature consists of examples of chemistry questions found on typi-
cal ­entrance examinations used to screen applicants to ­allied health ­professional programs.
In ­addition, ­approximately 20% of the ­end-of-­chapter exercises have been changed.

a. sulfate ions
Allied Health Exam Connection b. water ions
The following questions are from these sources: c. hydrogen ions
1. Nursing School Entrance Exam © 2005, Learning Express, LLC. d. oxygen ions
2. McGraw-Hill’s Nursing School Entrance Exams by Thomas A. 9.133 When a solution has a pH of 7, it is:
Evangelist, Tamara B. Orr and Judy Unrein © 2009, The
McGraw-Hill Companies, Inc. a. a strong base

3. NSEE Nursing School Entrance Exams, 3rd Edition © 2009, b. a strong acid
Kaplan Publishing. c. a weak base
4. Cliffs Test Prep: Nursing School Entrance Exams by Fred N. d. neutral
Grayson © 2004, Wiley Publishing, Inc.
9.134 A common detergent has a pH of 11.0, so the detergent is:
5. Peterson’s Master the Nursing School and Allied Health Entrance
a. neutral
Exams, 18th Edition by Marion F. Gooding © 2008, Peterson’s,
a Nelnet Company. b. acidic
9.126 An acid is a substance that dissociates in water into one or more c. alkaline
_______ ions and one or more _______. d. none of the above
a. hydrogen . . . anions 9.135 In a 0.001 M solution of HCl, the pH is:
b. hydrogen . . . cations a. 2
c. hydroxide . . . anions b. 23
d. hydroxide . . . cations c. 1

Also new to this edition are many new photographs and updated art to further enhance
student comprehension of key concepts, processes, and preparation.


+


+

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+


+

– – – –
+
+

+
+


+

– – – –
– –
+

+
+

– – – – – – –
+
+


+

© Spencer L. Seager

© Spencer L. Seager
© Spencer L. Seager

1 2 3
Step 1. Put 0.125 mol of solute into a Step 2. Add some water and dissolve Step 3. Fill the flask to the mark with
250-mL flask. the solute. water. Mix thoroughly.

Figure 7.8 Preparation of a 0.500 M solution. Use the data given in the and show by
a calculation that the resulting solution is 0.500 M.

xx   Preface Unless otherwise noted all art on this page © Cengage Learning 2014

Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Revision Summary of Eighth Edition:
Chapter 1:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Ask an Expert: Does Food Density Matter When You’re Trying to Lose Weight?
• New Chemistry Around Us: Effects of Temperature on Body Function
• 20% new Exercises

Chapter 2:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• Updated element table
• New Chemistry Around Us: Looking at Atoms
• New At the Counter: Nonprescription Medicines
• 20% new Exercises

Chapter 3:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Chemistry and Your Health: Iron: Too Much of a Good Thing?
• New Ask an Expert: Are Calcium Supplements Necessary?
• 20% new Exercises

Chapter 4:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Chemistry Around Us: Rare Earths Are All Around You
• 20% new Exercises

Chapter 5:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Chemistry Around Us: Redox Reactions and Energy for Life
• 20% new Exercises

Chapter 6:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Chemistry Around Us: Blood Pressure: A Barometer of Health
• 20% new Exercises

Chapter 7:
• New Case Study
• New Case Study Follow-up
• Several revised figures
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Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
• New photography
• New Chemistry and Your Health: The Risk of Dehydration During Vigorous Youth
Activities
• 20% new Exercises

Chapter 8:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• 20% new Exercises

Chapter 9:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Ask an Expert: Does Diet Play a Role in Peptic Ulcer Disease?
• New Chemistry Around Us: Carbon Dioxide in the Oceans
• 20% new Exercises

Chapter 10:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Chemistry Around Us: Radiation Exposure in Modern Life
• 20% new Exercises

Chapter 11:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Ask an Expert: Is Organic Food Worth the Price?
• New Chemistry Around Us: Oil Production from Wells and Sands
• 20% new Exercises

Chapter 12:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• 20% new Exercises

Chapter 13:
• New Case Study
• New Case Study Follow-up
• Several revised figures
• New photography
• New Chemistry Around Us: Alcohol and Antidepressants Don’t Mix
• New Chemistry And Your Health: Why Do Teens Drink?
• New Ask an Expert: What Are Polyphenols?
• 20% new Exercises

Chapter 14:
• New Case Study
• New Case Study Follow-up

xxii   Preface Unless otherwise noted all art on this page © Cengage Learning 2014

Copyright 2012 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.

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