Principles of General, Organic, & Biological Chemistry

656 Pages·2011·41.927 MB·English

by  Janice Smith

Janice Gor ynski Smith
-
niversity of H noa
TM
TM
PRINCIPLES OF GENERAL, ORGANIC, & BIOLOGICAL CHEMISTRY
Published by McGraw-Hill, a business unit of The McGraw-Hill Companies, Inc., 1221 Avenue of the Americas,
New York, NY 10020. Copyright © 2012 by The McGraw-Hill Companies, Inc. All rights reserved. No part of this
publication may be reproduced or distributed in any form or by any means, or stored in a database or retrieval system,
without the prior written consent of The McGraw-Hill Companies, Inc., including, but not limited to, in any network or
other electronic storage or transmission, or broadcast for distance learning.
Some ancillaries, including electronic and print components, may not be available to customers outside the United
States.
This book is printed on acid-free paper.
1 2 3 4 5 6 7 8 9 0 DOW/DOW 1 0 9 8 7 6 5 4 3 2 1
ISBN 978–0–07–351115–3
MHID 0–07–351115–3
Vice President, Editor-in-Chief: Marty Lange
Vice President, EDP: Kimberly Meriwether David
Senior Director of Development: Kristine Tibbetts
Publisher: Ryan Blankenship
Sponsoring Editor: Todd L. Turner
Senior Developmental Editor: Donna Nemmers
Executive Marketing Manager: Tamara L. Hodge
Senior Project Manager: Jayne L. Klein
Senior Buyer: Laura Fuller
Senior Media Project Manager: Christina Nelson
Senior Designer: Laurie B. Janssen
Cover Image: © Matt Brasier / Masterfi le
Lead Photo Research Coordinator: Carrie K. Burger
Photo Research: Mary Reeg
Compositor: Precision Graphics
Typeface: 10/12.5 Times LT Std
Printer: R. R. Donnelley
All credits appearing on page or at the end of the book are considered to be an extension of the copyright page.
Library of Congress Cataloging-in-Publication Data
Smith, Janice G.
Principles of general, organic, and biological chemistry / Janice Gorzynski Smith. -- 1st ed.
p. cm.
Includes index.
ISBN 978–0–07–351115–3 — ISBN 0–07–351115–3 (hard copy : alk. paper) 1. Chemistry--Textbooks. 2.
Chemistry, Inorganic--Textbooks. 3. Biochemistry--Textbooks. I. Title.
QD31.3.S634 2012
540--dc22
2010038944
www.mhhe.com
T
o my family
About the Author
Janice Gorzynski Smith was born in Schenectady, New York, and grew up following
the Yankees, listening to the Beatles, and water skiing on Sacandaga Reservoir. She became
interested in chemistry in high school, and went on to major in chemistry at Cornell University
where she received an A.B. degree summa cum laude. Jan earned a Ph.D. in Organic Chemistry
from Harvard University under the direction of Nobel Laureate E. J. Corey, and she also spent a
year as a National Science Foundation National Needs Postdoctoral Fellow at Harvard. During
her tenure with the Corey group she completed the total synthesis of the plant growth hormone
gibberellic acid.
Following her postdoctoral work Jan joined the faculty of Mount Holyoke College, where
she was employed for 21 years. During this time she was active in teaching organic chemis-
try lecture and lab courses, conducting a research program in organic 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. She is a faculty member at the University of Hawai‘i at Ma-noa, where she has taught a
one-semester organic and biological chemistry course for nursing students as well as the two-
semester organic chemistry lecture and lab courses. She has also served as the faculty advisor to
the student affi liate chapter of the American Chemical Society. In 2003, she received the Chan-
cellor’s Citation for Meritorious Teaching.
Jan resides in Hawai‘i with her husband Dan, an emergency medicine physician. She has
four children: Matthew and Zachary (scuba photo on p. 167); Jenna, a law student at Temple
University in Philadelphia; and Erin, a 2006 graduate of Brown University School of Medicine
and co-author of the Student Study Guide/Solutions Manual for this text. 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.
iv
Contents in Brief
1 Matter and Measurement 1
2 Atoms and the Periodic Table 34
3 Ionic and Covalent Compounds 68
4 Energy and Matter 105
5 Chemical Reactions 127
6 Gases 167
7 Solutions 194
8 Acids and Bases 222
9 Nuclear Chemistry 256
10 Introduction to Organic Molecules 283
11 Unsaturated Hydrocarbons 322
12 Organic Compounds That Contain Oxygen or Sulfur 353
13 Carboxylic Acids, Esters, Amines, and Amides 391
14 Carbohydrates 427
15 Lipids 459
16 Amino Acids, Proteins, and Enzymes 492
17 Nucleic Acids and Protein Synthesis 527
18 Energy and Metabolism 560
v
Contents
Preface xi
Acknowledgments xvii
List of How To’s xix
List of Applications xx
1
Matter and Measurement 1
1.1 Chemistry—The Science of Everyday Experience 2
1.2 States of Matter 3
1.3 Classifi cation of Matter 5
1.4 Measurement 9
1.5 Signifi cant Figures 12
1.6 Scientifi c Notation 16
1.7 Problem Solving Using the Factor–Label Method 19
1.8 FOCUS ON HEALTH & MEDICINE: Problem Solving Using Clinical
Conversion Factors 22
1.9 Temperature 24
1.10 Density and Specifi c Gravity 26
Study Skills Part I: Calculations in Chemistry 28
2
Atoms and the Periodic Table 34
2.1 Elements 35
2.2 Structure of the Atom 40
2.3 Isotopes 44
2.4 The Periodic Table 47
2.5 Electronic Structure 52
2.6 Electronic Confi gurations 54
2.7 Valence Electrons 57
2.8 Periodic Trends 59
3
Ionic and Covalent Compounds 68
3.1 Introduction to Bonding 69
3.2 Ions 70
3.3 Ionic Compounds 75
3.4 Naming Ionic Compounds 78
3.5 Physical Properties of Ionic Compounds 82
3.6 Polyatomic Ions 83
3.7 Covalent Bonding 86
3.8 Lewis Structures 88
3.9 Naming Covalent Compounds 89
vi
Contents vii
3.10 Molecular Shape 90
3.11 Electronegativity and Bond Polarity 94
3.12 Polarity of Molecules 96
4
Energy and Matter 105
4.1 Energy 106
4.2 The Three States of Matter 109
4.3 Intermolecular Forces 110
4.4 Boiling Point and Melting Point 114
4.5 Energy and Phase Changes 115
4.6 Heating and Cooling Curves 119
5
Chemical Reactions 127
5.1 Introduction to Chemical Reactions 128
5.2 Balancing Chemical Equations 132
5.3 The Mole and Avogadro’s Number 135
5.4 Mass to Mole Conversions 138
5.5 Mole Calculations in Chemical Equations 140
5.6 Mass Calculations in Chemical Equations 142
5.7 Oxidation and Reduction 148
5.8 Energy Changes in Reactions 152
5.9 Reaction Rates 155
5.10 FOCUS ON THE HUMAN BODY: Body Temperature 157
6
Gases 167
6.1 Gases and Pressure 168
6.2 Boyle’s Law Relating Gas Pressure and Volume 170
6.3 Charles’s Law Relating Gas Volume and Temperature 173
6.4 Gay–Lussac’s Law Relating Gas Pressure and Temperature 175
6.5 The Combined Gas Law 177
6.6 Avogadro’s Law Relating Gas Volume and Moles 178
6.7 The Ideal Gas Law 181
6.8 Dalton’s Law and Partial Pressures 184
6.9 FOCUS ON THE ENVIRONMENT: Ozone and Carbon Dioxide
in the Atmosphere 186
7
Solutions 194
7.1 Introduction 195
7.2 Solubility—General Features 197
7.3 Solubility—Effects of Temperature and Pressure 200
7.4 Concentration Units—Percent Concentration 202
7.5 Concentration Units—Molarity 206
7.6 Dilution 209
7.7 Osmosis and Dialysis 212
viii Contents
8
Acids and Bases 222
8.1 Introduction to Acids and Bases 223
8.2 The Reaction of a Brønsted–Lowry Acid with a Brønsted–Lowry Base 228
8.3 Acid and Base Strength 230
8.4 Dissociation of Water 234
8.5 The pH Scale 237
8.6 Common Acid–Base Reactions 241
8.7 Titration 244
8.8 Buffers 245
8.9 FOCUS ON THE HUMAN BODY: Buffers in the Blood 248
9
Nuclear Chemistry 256
9.1 Introduction 257
9.2 Nuclear Reactions 260
9.3 Half-Life 266
9.4 Detecting and Measuring Radioactivity 268
9.5 FOCUS ON HEALTH & MEDICINE: Medical Uses of Radioisotopes 270
9.6 Nuclear Fission and Nuclear Fusion 273
9.7 FOCUS ON HEALTH & MEDICINE: Medical Imaging Without Radioactivity 275
10
Introduction to Organic Molecules 283
10.1 Introduction to Organic Chemistry 284
10.2 Characteristic Features of Organic Compounds 285
10.3 Drawing Organic Molecules 288
10.4 Functional Groups 291
10.5 Alkanes 297
10.6 Alkane Nomenclature 302
10.7 Cycloalkanes 307
10.8 FOCUS ON THE ENVIRONMENT: Fossil Fuels 309
10.9 Physical Properties 310
10.10 FOCUS ON THE ENVIRONMENT: Combustion 311
Study Skills Part II: Organic Chemistry 312
11
Unsaturated Hydrocarbons 322
11.1 Alkenes and Alkynes 323
11.2 Nomenclature of Alkenes and Alkynes 325
11.3 Cis–Trans Isomers 327
11.4 FOCUS ON HEALTH & MEDICINE: Oral Contraceptives 331
11.5 Reactions of Alkenes 332
11.6 FOCUS ON HEALTH & MEDICINE: Margarine or Butter? 334
11.7 Polymers—The Fabric of Modern Society 336
11.8 Aromatic Compounds 340
11.9 Nomenclature of Benzene Derivatives 340
11.10 FOCUS ON HEALTH & MEDICINE: Sunscreens and Antioxidants 343
Contents ix
12
Organic Compounds That Contain Oxygen or Sulfur 353
12.1 Introduction 354
12.2 Structure and Properties of Alcohols 355
12.3 Structure and Properties of Ethers 358
12.4 Interesting Alcohols and Ethers 360
12.5 Reactions of Alcohols 361
12.6 Thiols 366
12.7 Structure and Properties of Aldehydes and Ketones 367
12.8 FOCUS ON HEALTH & MEDICINE: Interesting Aldehydes and Ketones 370
12.9 Oxidation of Aldehydes 371
12.10 Looking Glass Chemistry—Molecules and Their Mirror Images 373
12.11 FOCUS ON HEALTH & MEDICINE: Chiral Drugs 378
13
Carboxylic Acids, Esters, Amines, and Amides 391
13.1 Introduction 392
13.2 Nomenclature of Carboxylic Acids and Esters 393
13.3 Physical Properties of Carboxylic Acids and Esters 395
13.4 Interesting Carboxylic Acids in Consumer Products and Medicines 396
13.5 The Acidity of Carboxylic Acids 398
13.6 Reactions Involving Carboxylic Acids and Esters 401
13.7 Amines 404
13.8 Amines as Bases 409
13.9 Amides 412
13.10 Interesting Amines and Amides 415
14
Carbohydrates 427
14.1 Introduction 428
14.2 Monosaccharides 429
14.3 The Cyclic Forms of Monosaccharides 435
14.4 Reactions of Monosaccharides 438
14.5 Disaccharides 441
14.6 Polysaccharides 445
14.7 FOCUS ON THE HUMAN BODY: Blood Type 448
Study Skills Part III: Biomolecules 450
15
Lipids 459
15.1 Introduction to Lipids 460
15.2 Fatty Acids 461
15.3 Waxes 463
15.4 Triacylglycerols—Fats and Oils 465
15.5 Hydrolysis of Triacylglycerols 469
15.6 Phospholipids 472
15.7 Cell Membranes 474
15.8 FOCUS ON HEALTH & MEDICINE: Cholesterol, the Most Prominent Steroid 476
x Contents
15.9 Steroid Hormones 479
15.10 FOCUS ON HEALTH & MEDICINE: Fat-Soluble Vitamins 481
16
Amino Acids, Proteins, and Enzymes 492
16.1 Introduction 493
16.2 Amino Acids 494
16.3 Acid–Base Behavior of Amino Acids 497
16.4 Peptides 499
16.5 FOCUS ON THE HUMAN BODY: Biologically Active Peptides 502
16.6 Proteins 504
16.7 FOCUS ON THE HUMAN BODY: Common Proteins 508
16.8 Protein Hydrolysis and Denaturation 511
16.9 Enzymes 514
16.10 FOCUS ON HEALTH & MEDICINE: Using Enzymes to Diagnose
and Treat Diseases 518
17
Nucleic Acids and Protein Synthesis 527
17.1 Nucleosides and Nucleotides 528
17.2 Nucleic Acids 533
17.3 The DNA Double Helix 535
17.4 Replication 538
17.5 RNA 540
17.6 Transcription 541
17.7 The Genetic Code 542
17.8 Translation and Protein Synthesis 544
17.9 Mutations and Genetic Diseases 547
17.10 FOCUS ON THE HUMAN BODY: DNA Fingerprinting 549
17.11 FOCUS ON HEALTH & MEDICINE: Viruses 549
18
Energy and Metabolism 560
18.1 An Overview of Metabolism 561
18.2 ATP and Energy Production 564
18.3 Coenzymes in Metabolism 566
18.4 Glycolysis 569
18.5 The Fate of Pyruvate 573
18.6 The Citric Acid Cycle 576
18.7 The Electron Transport Chain and Oxidative Phosphorylation 579
18.8 The ATP Yield from Glucose 582
18.9 The Catabolism of Triacylglycerols 584
18.10 Ketone Bodies 587
18.11 Amino Acid Metabolism 588
Appendix Useful Mathematical Concepts A-1
Glossary G-1
Credits C-1
Index I-1