Janice Gorzynski Smith - University of Hawai’i at Manoa GENERAL, ORGANIC, AND 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 © 2010 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 0 9 ISBN 978–0–07–302657–2 MHID 0–07–302657–3 Publisher: Thomas D. Timp Senior Sponsoring Editor: Tamara L. Hodge Vice-President New Product Launches: Michael Lange Senior Developmental Editor: Donna Nemmers Marketing Manager: Todd L. Turner Senior Project Manager: Jayne L. Klein Senior Production Supervisor: Laura Fuller Senior Media Project Manager: Tammy Juran Designer: Laurie B. Janssen (USE) Cover Image: Lower right: ©3D4Medical.com/gettyimages, background: ©Andrew Brookes/Corbis Lead Photo Research Coordinator: Carrie K. Burger Photo Research: Mary Reeg Supplement Producer: Mary Jane Lampe Compositor: Precision Graphics Typeface: 10/12.5 Times LT Std Printer: R. R. Donnelley Willard, OH The credits section for this book begins on page C-1 and is considered an extension of the copyright page. Library of Congress Cataloging-in-Publication Data Smith, Janice G. General, organic, and biological chemistry / Janice Gorzynski Smith. — 1st ed. p. mc. Includes index. ISBN 978–0–07–302657–2 — ISBN 0–07–302657–3 (hard copy : alk. paper) 1. Chemistry—Textbooks. I. Title. QD31.3.S63 2010 540—dc22 2008044484 www.mhhe.com Dedication To my husband Dan, children Erin, Jenna, Matthew, and Zachary, and father Stanley, and in memory of my mother Dorothea and daughter Megan. About the Author Janice Gorzynski Smith was born in Schenectady, New York, and grew up follow- ing 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 chemistry 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 currently a faculty member at the University of Hawai‘i at Mā noa, where she teaches a one-semester organic and biological chemistry course for nursing students, as well as the two-semester organic chemistry lecture and lab courses. She also serves as the faculty advisor to the student affi liate chapter of the American Chemical Society. In 2003, she received the Chancellor’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 page 190); Jenna, a fi rst-year 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 Hawai‘ian quilting. vvii Brief Contents 1 Matter and Measurement 1 2 Atoms and the Periodic Table 32 3 Ionic Compounds 66 4 Covalent Compounds 93 5 Chemical Reactions 121 6 Energy Changes, Reaction Rates, and Equilibrium 159 7 Gases, Liquids, and Solids 190 8 Solutions 228 9 Acids and Bases 258 10 Nuclear Chemistry 298 11 Introduction to Organic Molecules and Functional Groups 322 12 Alkanes 355 13 Unsaturated Hydrocarbons 379 14 Organic Compounds That Contain Oxygen, Halogen, or Sulfur 418 15 The Three-Dimensional Shape of Molecules 449 16 Aldehydes and Ketones 473 17 Carboxylic Acids, Esters, and Amides 503 18 Amines and Neurotransmitters 540 19 Lipids 569 20 Carbohydrates 608 21 Amino Acids, Proteins, and Enzymes 644 22 Nucleic Acids and Protein Synthesis 682 23 Digestion and the Conversion of Food into Energy 718 24 Carbohydrate, Lipid, and Protein Metabolism 744 vviiii Contents Preface xxii P.A.V.E. the Way to Student Learning xxiv Acknowledgments xxvii List of How To’s xxix List of Applications xxx 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 8 1.4A The Metric System 8 1.4B Measuring Length 10 1.4C Measuring Mass 10 1.4D Measuring Volume 10 1.5 Signifi cant Figures 11 1.5A Determining the Number of Signifi cant Figures 12 1.5B Using Signifi cant Figures in Multiplication and Division 13 1.5C Using Signifi cant Figures in Addition and Subtraction 15 1.6 Scientifi c Notation 16 1.7 Problem Solving Using the Factor–Label Method 18 1.7A Conversion Factors 18 1.7B Solving a Problem Using One Conversion Factor 19 1.7C Solving a Problem Using Two or More Conversion Factors 21 1.8 Focus on Health & Medicine: Problem Solving Using Clinical Conversion Factors 22 1.9 Temperature 24 1.10 Density and Specifi c Gravity 25 1.10A Density 25 1.10B Specifi c Gravity 27 Chapter Highlights 27 ix x CONTENTS 2 Atoms and the Periodic Table 32 2.1 Elements 33 2.1A Elements and the Periodic Table 34 2.1B Focus on the Human Body: The Elements of Life 34 2.1C Compounds 36 2.2 Structure of the Atom 37 2.3 Isotopes 40 2.3A Isotopes, Atomic Number, and Mass Number 41 2.3B Atomic Weight 42 2.3C Focus on Health & Medicine: Isotopes in Medicine 43 2.4 The Periodic Table 44 2.4A Basic Features of the Periodic Table 44 2.4B Characteristics of Groups 1A, 2A, 7A, and 8A 46 2.4C The Unusual Nature of Carbon 48 2.5 Electronic Structure 48 2.6 Electronic Confi gurations 51 2.6A First-Row Elements (Period 1) 52 2.6B Second-Row Elements (Period 2) 53 2.6C Other Elements 54 2.7 Electronic Confi gurations and the Periodic Table 55 2.7A Valence Electrons 56 2.7B Electron-Dot Symbols 58 2.8 Periodic Trends 59 2.8A Atomic Size 59 2.8B Ionization Energy 60 Chapter Highlights 61 3 Ionic Compounds 66 3.1 Introduction to Bonding 67 3.2 Ions 68 3.2A Cations and Anions 68 3.2B Relating Group Number to Ionic Charge for Main Group Elements 71 3.2C Metals with Variable Charge 73 3.2D Focus on the Human Body: Important Ions in the Body 74 3.3 Ionic Compounds 75 3.3A Formulas for Ionic Compounds 76 3.3B Focus on Health & Medicine: Ionic Compounds in Consumer Products 78 3.4 Naming Ionic Compounds 79 3.4A Naming Cations 79 3.4B Naming Anions 80 3.4C Naming Ionic Compounds with Cations from Main Group Metals 80 3.4D Naming Ionic Compounds Containing Metals with Variable Charge 81 3.4E Writing a Formula from the Name of an Ionic Compound 82 3.5 Physical Properties of Ionic Compounds 83 3.6 Polyatomic Ions 83 3.6A Writing Formulas for Ionic Compounds with Polyatomic Ions 85 3.6B Naming Ionic Compounds with Polyatomic Ions 86 3.6C Focus on Health & Medicine: Useful Ionic Compounds 87 3.6D Focus on Health & Medicine: Treating Osteoporosis 87 Chapter Highlights 88