Hydrogen 8A Period 1 (18) number 1 H Uranium Helium Group number, 1.0079 METALS 92 Atomic number 2 U.S. system 1A 2A 3A 4A 5A 6A 7A He Group number, (1) (2) METALLOIDS U Symbol (13) (14) (15) (16) (17) 4.0026 IUPAC system Lithium Beryllium Boron Carbon Nitrogen Oxygen Fluorine Neon NONMETALS 238.0289 Atomic weight 3 4 5 6 7 8 9 10 2 Li Be B C N O F Ne 6.941 9.0122 10.811 12.011 14.0067 15.9994 18.9984 20.1797 Sodium Magnesium Aluminum Silicon Phosphorus Sulfur Chlorine Argon 11 12 13 14 15 16 17 18 3 Na Mg 3B 4B 5B 6B 7B 8B 1B 2B Al Si P S Cl Ar 22.9898 24.3050 (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) 26.9815 28.0855 30.9738 32.066 35.4527 39.948 Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 4 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr 39.0983 40.078 44.9559 47.867 50.9415 51.9961 54.9380 55.845 58.9332 58.6934 63.546 65.38 69.723 72.61 74.9216 78.96 79.904 83.80 Rubidium Strontium Yttrium Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 5 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe 85.4678 87.62 88.9059 91.224 92.9064 95.96 (97.907) 101.07 102.9055 106.42 107.8682 112.411 114.818 118.710 121.760 127.60 126.9045 131.29 Cesium Barium Lanthanum Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon 55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 6 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn 132.9054 137.327 138.9055 178.49 180.9488 183.84 186.207 190.2 192.22 195.084 196.9666 200.59 204.3833 207.2 208.9804 (208.98) (209.99) (222.02) Francium Radium Actinium Rutherfordium Dubnium Seaborgium Bohrium Hassium Meitnerium Darmstadtium Roentgenium — — — — — — 87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116 118 7 Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg — — — — — — Discovered Discovered Discovered Discovered Discovered Discovered (223.02) (226.0254) (227.0278) (261.11) (262.11) (263.12) (262.12) (265) (266) (271) (272) 1996 2004 1999 2004 1999 2006 Cerium Praseodymium Neodymium Promethium Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium Lutetium 58 59 60 61 62 63 64 65 66 67 68 69 70 71 Lanthanides Note: Atomic masses are Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu 2007 IUPAC values (up to 140.115 140.9076 144.24 (144.91) 150.36 151.965 157.25 158.9253 162.50 164.9303 167.26 168.9342 173.54 174.9668 four decimal places). Thorium Protactinium Uranium Neptunium Plutonium Americium Curium Berkelium Californium Einsteinium Fermium Mendelevium Nobelium Lawrencium Numbers in parentheses are 90 91 92 93 94 95 96 97 98 99 100 101 102 103 atomic masses or mass Actinides Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr numbers of the most stable isotope of an element. 232.0381 231.0388 238.0289 (237.0482) (244.664) (243.061) (247.07) (247.07) (251.08) (252.08) (257.10) (258.10) (259.10) (262.11) STANDARD ATOMIC WEIGHTS OF THE ELEMENTS 2007 Based on relative atomic mass of 12C 5 12, where 12C is a neutral atom in its nuclear and electronic ground state.† Atomic Atomic Atomic Atomic Name Symbol Number Weight Name Symbol Number Weight Actinium* Ac 89 (227) Neodymium Nd 60 144.22(3) Aluminum Al 13 26.9815386(8) Neon Ne 10 20.1797(6) Americium* Am 95 (243) Neptunium* Np 93 (237) Antimony Sb 51 121.760(1) Nickel Ni 28 58.6934(4) Argon Ar 18 39.948(1) Niobium Nb 41 92.90638(2) Arsenic As 33 74.92160(2) Nitrogen N 7 14.0067(2) Astatine* At 85 (210) Nobelium* No 102 (259) Barium Ba 56 137.327(7) Osmium Os 76 190.23(3) Berkelium* Bk 97 (247) Oxygen O 8 15.9994(3) Beryllium Be 4 9.012182(3) Palladium Pd 46 106.42(1) Bismuth Bi 83 208.98040(1) Phosphorus P 15 30.973762(2) Bohrium Bh 107 (264) Platinum Pt 78 195.084(9) Boron B 5 10.811(7) Plutonium* Pu 94 (244) Bromine Br 35 79.904(1) Polonium* Po 84 (209) Cadmium Cd 48 112.411(8) Potassium K 19 39.0983(1) Cesium Cs 55 132.9054519(2) Praseodymium Pr 59 140.90765(2) Calcium Ca 20 40.078(4) Promethium* Pm 61 (145) Californium* Cf 98 (251) Protactinium* Pa 91 231.03588(2) Carbon C 6 12.0107(8) Radium* Ra 88 (226) Cerium Ce 58 140.116(1) Radon* Rn 86 (222) Chlorine Cl 17 35.453(2) Rhenium Re 75 186.207(1) Chromium Cr 24 51.9961(6) Rhodium Rh 45 102.90550(2) Cobalt Co 27 58.933195(5) Roentgenium Rg 111 (272) Copper Cu 29 63.546(3) Rubidium Rb 37 85.4678(3) Curium* Cm 96 (247) Ruthenium Ru 44 101.07(2) Darmstadtium Ds 110 (271) Rutherfordium Rf 104 (261) Dubnium Db 105 (262) Samarium Sm 62 150.36(2) Dysprosium Dy 66 162.500(1) Scandium Sc 21 44.955912(6) Einsteinium* Es 99 (252) Seaborgium Sg 106 (266) Erbium Er 68 167.259(3) Selenium Se 34 78.96(3) Europium Eu 63 151.964(1) Silicon Si 14 28.0855(3) Fermium* Fm 100 (257) Silver Ag 47 107.8682(2) Fluorine F 9 18.9984032(5) Sodium Na 11 22.9896928(2) Francium* Fr 87 (223) Strontium Sr 38 87.62(1) Gadolinium Gd 64 157.25(3) Sulfur S 16 32.065(5) Gallium Ga 31 69.723(1) Tantalum Ta 73 180.9488(2) Germanium Ge 32 72.64(1) Technetium* Tc 43 (98) Gold Au 79 196.966569(4) Tellurium Te 52 127.60(3) Hafnium Hf 72 178.49(2) Terbium Tb 65 158.92535(2) Hassium Hs 108 (277) Thallium Tl 81 204.3833(2) Helium He 2 4.002602(2) Thorium* Th 90 232.03806(2) Holmium Ho 67 164.93032(2) Thulium Tm 69 168.93421(2) Hydrogen H 1 1.00794(7) Tin Sn 50 118.710(7) Indium In 49 114.818(3) Titanium Ti 22 47.867(1) Iodine I 53 126.90447(3) Tungsten W 74 183.84(1) Iridium Ir 77 192.217(3) Ununbium Uub 112 (285) Iron Fe 26 55.845(2) Ununhexium Uuh 116 (292) Krypton Kr 36 83.798(2) Ununoctium Uuo 118 (294) Lanthanum La 57 138.90547(7) Ununpentium Uup 115 (228) Lawrencium* Lr 103 (262) Ununquadium Uuq 114 (289) Lead Pb 82 207.2(1) Ununtrium Uut 113 (284) Lithium Li 3 6.941(2) Uranium* U 92 238.02891(3) Lutetium Lu 71 174.9668(1) Vanadium V 23 50.9415(1) Magnesium Mg 12 24.3050(6) Xenon Xe 54 131.293(6) Manganese Mn 25 54.938045(5) Ytterbium Yb 70 173.54(5) Meitnerium Mt 109 (268) Yttrium Y 39 88.90585(2) Mendelevium* Md 101 (258) Zinc Zn 30 65.38(2) Mercury Hg 80 200.59(2) Zirconium Zr 40 91.224(2) Molybdenum Mo 42 95.96(2) †The atomic weights of many elements can vary depending on the origin *Elements with no stable nuclide; the value given in parentheses is the and treatment of the sample. This is particularly true for Li; commercially atomic mass number of the isotope of longest known half-life. However, available lithium-containing materials have Li atomic weights in the three such elements (Th, Pa, and U) have a characteristic terrestial isoto- range of 6.939 and 6.996. The uncertainties in atomic weight values are pic composition, and the atomic weight is tabulated for these. http://www given in parentheses following the last significant figure to which they are . chem.qmw.ac.uk/iupac/AtWt/ attributed. Study smarter and improve your grade For General, Organic, and Biochemistry Developed at the University of Massachusetts, Amherst, and class tested by tens of thousands of chemistry students, OWL is a fully customizable and fl exible web-based learning system. OWL supports mastery learning and offers numerical, chemical and contextual parameterization to produce thousands of problems correlated to this text. The OWL system also features a database of simulations, tutorials, and exercises, as well as end-of-chapter problems from the text. With OWL, you get the most widely used online learning system available for chemistry with unsurpassed reliability and dedicated training and support. Features (cid:2) Interactive simulations of chemical systems are accompanied by guiding questions that lead you through an exploration of the simulation. These concept-building tools guide you to your own discovery of chemical concepts and relationships. (cid:2) Interactive problem-solving tutors ask questions and then give feedback that helps you solve the problem. (cid:2) Explorations of animations, movies and graphic images help you examine the chemical principles behind multimedia presentations of chemical events. (cid:2) Re-try questions over and over, covering the same concept, but using different numerical values and chemical systems until you get it right. 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If not, visit www.ichapters.com, our preferred online store, to purchase access to other helpful products from Cengage Learning. 9911112233__3366__SSEE--EEnnddsshheeeett__pp000011--000088..iinn44 44 1111//2244//0088 1100::5599::1177 AAMM INTRODUCTION TO General, Organic, and Biochemistry NINTH EDITION Frederick A. Bettelheim William H. Brown Beloit College Mary K. Campbell Mount Holyoke College Shawn O. Farrell Olympic Training Center Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States Introduction to General, Organic, © 2010 Brooks/Cole, Cengage Learning and Biochemistry, Ninth Edition ALL RIGHTS RESERVED. No part of this work covered by the copyright herein Frederick A. Bettelheim, William H. Brown, may be reproduced, transmitted, stored or used in any form or by any means Mary K. Campbell, Shawn O. 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Locate your local offi ce at: David Hart (Center for Educational Software international.cengage.com/region Development, University of Massachusetts, Amherst) Cengage Learning products are represented in Canada by Nelson Education, Ltd. Cover Designer: John Walker Cover Image: Lester Lefkowitz/CORBIS For your course and learning solutions, visit academic.cengage.com Compositor: Pre-Press PMG Purchase any of our products at your local college store or at our preferred online store www.ichapters.com Printed in Canada 1 2 3 4 5 6 7 12 10 09 08 To my lovely wife, Courtney — Between textbook revisions, a full-time job, and school, I have been little more than a ghost around the house, hiding in my study writing. Courtney held the family together, taking care of our children and our home while maintaining her own writing schedule. None of this would have been possible without her love, support, and tireless effort. —SF To my grandchildren for the love and joy they bring to my life: Emily, Sophia, and Oscar; Amanda and Laura; Rachel; Gabrielle and Max. —WB To Andrew, Christian, and Sasha — Thank you for the rewards of being your mom. And to Bill, Mary, and Shawn. — It is always a pleasure to work with you. —SK Contents in Brief General Chemistry Chapter 1 Matter, Energy, and Measurement 1 Chapter 2 Atoms 31 Chapter 3 Chemical Bonds 68 Chapter 4 Chemical Reactions 108 Chapter 5 Gases, Liquids, and Solids 141 Chapter 6 Solutions and Colloids 178 Chapter 7 Reaction Rates and Chemical Equilibrium 210 Chapter 8 Acids and Bases 240 Chapter 9 Nuclear Chemistry 276 Organic Chemistry Chapter 10 Organic Chemistry 307 Chapter 11 Alkanes 323 Chapter 12 Alkenes and Alkynes 352 Chapter 13 Benzene and Its Derivatives 382 Chapter 14 Alcohols, Ethers, and Thiols 397 Chapter 15 Chirality: The Handedness of Molecules 420 Chapter 16 Amines 441 Chapter 17 Aldehydes and Ketones 457 Chapter 18 Carboxylic Acids 475 Chapter 19 Carboxylic Anhydrides, Esters, and Amides 498 iv Contents in Brief ■ v Biochemistry Chapter 20 Carbohydrates 517 Chapter 21 Lipids 546 Chapter 22 Proteins 578 Chapter 23 Enzymes 614 Chapter 24 Chemical Communicators: Neurotransmitters and Hormones 639 Chapter 25 Nucleotides, Nucleic Acids, and Heredity 665 Chapter 26 Gene Expression and Protein Synthesis 695 Chapter 27 Bioenergetics: How the Body Converts Food to Energy 726 Chapter 28 Specifi c Catabolic Pathways: Carbohydrate, Lipid, and Protein Metabolism 747 Chapter 29 Biosynthetic Pathways 772 Chapter 30 Nutrition 787 Chapter 31 Immunochemistry 809 Chapter 32 Body Fluids (Chapter 32 can be found on this book’s companion website, which is accessible from www.cengage.com/chemistry/bettelheim) Contents Chapter 1 Matter, Energy, 2D Strontium-90 45 and Measurement 1 2E The Use of Metals as Historical Landmarks 47 1.1 Why Do We Call Chemistry the Study of Matter? 1 Chapter 3 Chemical Bonds 68 1.2 What Is the Scientifi c Method? 3 1.3 How Do Scientists Report Numbers? 5 3.1 What Do We Need to Know Before We Begin? 68 How To... Determine the Number of Signifi cant 3.2 What Is the Octet Rule? 69 Figures in a Number 6 3.3 How Do We Name Anions and Cations? 71 3.4 What Are the Two Major Types of Chemical Bonds? 73 1.4 How Do We Make Measurements? 8 3.5 What Is an Ionic Bond? 75 1.5 What Is a Handy Way to Convert from One Unit to 3.6 How Do We Name Ionic Compounds? 77 Another? 12 3.7 What Is a Covalent Bond? 79 How To... Do Unit Conversions by the Factor- How To... Draw Lewis Structures 82 Label Method 13 3.8 How Do We Name Binary Covalent 1.6 What Are the States of Matter? 17 Compounds? 87 1.7 What Are Density and Specifi c Gravity? 18 3.9 What Is Resonance? 89 1.8 How Do We Describe the Various Forms of How To... Draw Curved Arrows and Push Energy? 20 1.9 How Do We Describe Heat and the Ways in Which It Electrons 90 Is Transferred? 21 3.10 How Do We Predict Bond Angles in Covalent Molecules? 92 Summary of Key Questions 26 3.11 How Do We Determine if a Molecule Is Polar? 96 Problems 26 Chemical Connections Summary of Key Questions 98 Problems 100 1A Drug Dosage and Body Mass 11 Chemical Connections 1B Hypothermia and Hyperthermia 22 1C Cold Compresses, Waterbeds, and Lakes 23 3A Coral Chemistry and Broken Bones 73 3B Ionic Compounds in Medicine 80 Chapter 2 Atoms 31 3C Nitric Oxide: Air Pollutant and Biological Messenger 88 2.1 What Is Matter Made Of? 31 2.2 How Do We Classify Matter? 32 Chapter 4 Chemical Reactions 108 2.3 What Are the Postulates of Dalton’s Atomic Theory? 35 2.4 What Are Atoms Made Of? 38 4.1 What Is a Chemical Reaction? 108 2.5 What Is the Periodic Table? 43 4.2 What Are Formula Weights 2.6 How Are the Electrons in an Atom Arranged? 49 and Molecular Weights? 109 2.7 How Are Electron Confi guration and Position in the 4.3 What Is a Mole and How Do Periodic Table Related? 56 We Use it to Calculate Mass 2.8 What Is a Periodic Property? 57 Relationships? 110 Summary of Key Questions 60 4.4 How Do We Balance Problems 61 Chemical Equations? 114 Chemical Connections How To... Balance a Chemical Equation 114 2A Elements Necessary for Human Life 33 2B Abundance of Elements Present in the Human Body 4.5 How Do We Calculate Mass and Earth’s Crust 37 Relationships in Chemical 2C Isotopic Abundance and Astrochemistry 43 Reactions? 118 vi