00 55 00 88 44 __ ee nn dd shsh ee ee t_t_ pp tgtg 00 11 __ 00 00 11 -008.indd 2-008.indd 2 PnGuerrmoiuobpde rnumbe1r, H1y.d0Hr10o7g9en METALS Ura9n2ium Atomic number H(e81l2Ai8u)m 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 Copernicium — — — — — — 87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 7 Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg Cn — — — — — — Discovered Discovered Discovered Discovered Discovered (223.02) (226.0254) (227.0278) (261.11) (262.11) (263.12) (262.12) (265) (266) (271) (272) (285) 2004 1999 2004 1999 (292) 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) 00 66 /1/1 00 /1/1 11 6 6 :4:4 22 P P MM STANDARD ATOMIC WEIGHTS OF THE ELEMENTS 2010 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) Molybdenum Mo 42 95.96(2) Aluminum Al 13 26.9815386(8) Neodymium Nd 60 144.22(3) Americium* Am 95 (243) Neon Ne 10 20.1797(6) Antimony Sb 51 121.760(1) Neptunium* Np 93 (237) Argon Ar 18 39.948(1) Nickel Ni 28 58.6934(4) Arsenic As 33 74.92160(2) Niobium Nb 41 92.90638(2) Astatine* At 85 (210) Nitrogen N 7 14.0067(2) Barium Ba 56 137.327(7) Nobelium* No 102 (259) Berkelium* Bk 97 (247) Osmium Os 76 190.23(3) Beryllium Be 4 9.012182(3) Oxygen O 8 15.9994(3) Bismuth Bi 83 208.98040(1) Palladium Pd 46 106.42(1) Bohrium Bh 107 (264) Phosphorus P 15 30.973762(2) Boron B 5 10.811(7) Platinum Pt 78 195.084(9) Bromine Br 35 79.904(1) Plutonium* Pu 94 (244) Cadmium Cd 48 112.411(8) Polonium* Po 84 (209) Cesium Cs 55 132.9054519(2) Potassium K 19 39.0983(1) Calcium Ca 20 40.078(4) Praseodymium Pr 59 140.90765(2) Californium* Cf 98 (251) Promethium* Pm 61 (145) Carbon C 6 12.0107(8) Protactinium* Pa 91 231.03588(2) Cerium Ce 58 140.116(1) Radium* Ra 88 (226) Chlorine Cl 17 35.453(2) Radon* Rn 86 (222) Chromium Cr 24 51.9961(6) Rhenium Re 75 186.207(1) Cobalt Co 27 58.933195(5) Rhodium Rh 45 102.90550(2) Copernicium* Cn 112 (285) 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) Ununhexium Uuh 116 (292) Iron Fe 26 55.845(2) Ununoctium Uuo 118 (294) Krypton Kr 36 83.798(2) Ununpentium Uup 115 (228) Lanthanum La 57 138.90547(7) Ununquadium Uuq 114 (289) Lawrencium* Lr 103 (262) Ununseptium Uus 117 (292) 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) †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. 0055008844__eennddsshheeeett__ppttgg0011__000011--000088..iinndddd 33 0066//1100//1111 66::4422 PPMM Get a Better Grade in Chemistry! Log in now to the leading online learning system for chemistry. Score better on exams, access step-by-step solutions, and more! • Master chemistry and improve your grade using OWL’s step-by-step tutorials, interactive simulations, and homework questions that provide instant answer-specifi c feedback. Available 24/7. • Learn at your own pace with OWL, a study smart system that ensures you’ve mastered each concept before you move on. • Access the Cengage YouBook, a media-rich, interactive e-version of “OWL saved my grade in Chemistry.” your textbook. – Daniel D’Costa, Student, Hofstra University To get started, use the access code that may have been packaged with your text or purchase access online. Check with your instructor to verify that OWL is required for your course before purchasing. www.cengage.com/OWL 0055008844__eennddsshheeeett__ppttgg0011__000011--000088..iinndddd 44 0066//1100//1111 66::4422 PPMM This page intentionally left blank INTRODUCTION TO General, Organic, and Biochemistry TENTH EDITION Frederick A. Bettelheim William H. Brown Beloit College Mary K. Campbell Mount Holyoke College Shawn O. Farrell Olympic Training Center Omar J. Torres College of the Canyons Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States 0055008844__ffmm__ppttgg0011__ii--xxxxvviiiiii..iinndddd ii 0077//1100//1111 1100::1166 AAMM This is an electronic version of the print textbook. Due to electronic rights restrictions, some third party content may be suppressed. Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. The publisher reserves the right to remove content from this title at any time if subsequent rights restrictions require it. For valuable information on pricing, previous editions, changes to current editions, and alternate formats, please visit www.cengage.com/highered to search by ISBN#, author, title, or keyword for materials in your areas of interest. 0055008844__ffmm__ppttgg0011__ii--xxxxvviiiiii..iinndddd xxxxvviiiiii 0077//1100//1111 1100::1177 AAMM Introduction to General, Organic, © 2013, 2010 Brooks/Cole, Cengage Learning and Biochemistry, Tenth Edition ALL RIGHTS RESERVED. No part of this work covered by the copyright herein Frederick A. Bettelheim, William H. may be reproduced, transmitted, stored or used in any form or by any means Brown, Mary K. Campbell, Shawn O. Farrell, graphic, electronic, or mechanical, including but not limited to photocopying, Omar J. 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Trego Library of Congress Control Number: 2011934948 Design Director: Rob Hugel ISBN-13: 978-1-133-10508-4 Art Director: Maria Epes ISBN-10: 1-133-10508-4 Manufacturing Planner: Karen Hunt Rights Acquisitions Specialist: Dean Dauphinais Brooks/Cole Production Service: PreMediaGlobal 20 Davis Drive Belmont, CA 94002-3098 Text Designer: Bill Reuter Design USA Photo Researcher: Chris Altof/Bill Smith Group Text Researcher: Sue C. Howard Cengage Learning is a leading provider of customized learning solutions with Copy Editor: PreMediaGlobal offi ce locations around the globe, including Singapore, the United Kingdom, Illustrator: PreMediaGlobal, 2064 Design Australia, Mexico, Brazil, and Japan. Locate your local offi ce at: www.cengage.com/global OWL Producers: Stephen Battisti, Cindy Stein, David Hart (Center for Educational Software Development, University of Massachusetts, Cengage Learning products are represented in Canada by Nelson Education, Ltd. Amherst) Cover Designer: Bill Reuter Design For your course and learning solutions, visit academic.cengage.com Cover Images: Main image ©Dave Reede/Getty Images, from left to right ©Ottmar Diez/Getty Purchase any of our products at your local college store or at our preferred Images, ©Chris Hill/Getty Images, online store www.cengagebrain.com ©David Norton Photography/Alamy, © PhotoResearchers, Inc. Compositor: PreMediaGlobal Unless otherwise noted, all art appearing in this book is © Cengage Learning 2013. Printed in the United States of America 1 2 3 4 5 6 7 15 14 13 12 11 0055008844__ffmm__ppttgg0011__ii--xxxxvviiiiii..iinndddd iiii 0077//1100//1111 1100::1166 AAMM To Carolyn, with whom life is a joy. —WB To my family and friends – thank you for all your support. I couldn’t have done it without you. — MC 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 loving family and friends who have supported me through this journey: Mom, Dad, Lisa, Abuela, René, Ryan, Deanna, and Dianne. I could not have made it without your urging and support. I am truly blessed to have each of you in my life. — OT 0055008844__ffmm__ppttgg0011__ii--xxxxvviiiiii..iinndddd iiiiii 0077//1100//1111 1100::1166 AAMM 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 140 Chapter 6 Solutions and Colloids 177 Chapter 7 Reaction Rates and Chemical Equilibrium 210 Chapter 8 Acids and Bases 239 Chapter 9 Nuclear Chemistry 275 Organic Chemistry Chapter 10 Organic Chemistry 305 Chapter 11 Alkanes 322 Chapter 12 Alkenes and Alkynes 353 Chapter 13 Benzene and Its Derivatives 383 Chapter 14 Alcohols, Ethers, and Thiols 399 Chapter 15 Chirality: The Handedness of Molecules 423 Chapter 16 Amines 446 Chapter 17 Aldehydes and Ketones 464 Chapter 18 Carboxylic Acids 483 Chapter 19 Carboxylic Anhydrides, Esters, and Amides 508 iv 0055008844__ffmm__ppttgg0011__ii--xxxxvviiiiii..iinndddd iivv 0077//1100//1111 1100::1166 AAMM