Copyright 2016 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. 8A(18) Helium2He4.0026 Neon10Ne20.1797 Argon18Ar39.948 Krypton36Kr83.80 Xenon54Xe131.29 Radon86Rn(222.02) —118—Discovered2006 Lutetium71Lu174.9668 Lawrencium103Lr(262.11) 7A(17) Fluorine9F18.9984 Chlorine17Cl35.4527 Bromine35Br79.904 Iodine53I126.9045 Astatine85At(209.99) —117— (292) Ytterbium70Yb173.54 Nobelium102No(259.10) 6A(16) Oxygen8O15.9994 Sulfur16S32.066 Selenium34Se78.96 Tellurium52Te127.60 Polonium84Po(208.98) Livermorium116Lv(293) Thulium69Tm168.9342 Mendelevium101Md(258.10) 5A(15) Nitrogen7N14.0067 Phosphorus15P30.9738 Arsenic33As74.9216 Antimony51Sb121.760 Bismuth83Bi208.9804 —115—Discovered2004 Erbium68Er167.26 Fermium100Fm(257.10) 4A(14) Carbon6C12.011 Silicon14Si28.0855 Germanium32Ge72.61 Tin50Sn118.710 Lead82Pb207.2 Flerovium114Fl(289) Holmium67Ho164.9303 Einsteinium99Es(252.08) 3A(13) Boron5B10.811 Aluminum13Al26.9815 Gallium31Ga69.723 Indium49In114.818 Thallium81Tl204.3833 —113—Discovered2004 Dysprosium66Dy162.50 Californium98Cf(251.08) 2B(12) Zinc30Zn65.38 Cadmium48Cd112.411 Mercury80Hg200.59 Copernicium112Cn(285) Terbium65Tb158.9253 Berkelium97Bk(247.07) number weight 1B(11) Copper29Cu63.546 Silver47Ag107.8682 Gold79Au196.9666 Roentgenium111Rg(272) Gadolinium64Gd157.25 Curium96Cm(247.07) Atomic Symbol Atomic (10) Nickel28Ni58.6934 Palladium46Pd106.42 Platinum78Pt195.084 Darmstadtium110Ds(271) Europium63Eu151.965 Americium95Am(243.061) Uranium92U238.0289 8B (8)(9) IronCobalt2726FeCo55.84558.9332 RhodiumRuthenium4544RhRu102.9055101.07 IridiumOsmium7776OsIr192.22190.2 MeitneriumHassium109108MtHs(265)(266) PromethiumSamarium6162SmPm(144.91)150.36 PlutoniumNeptunium9493NpPu(244.664)(237.0482) DS LS 7B(7) Manganese25Mn54.9380 Technetium43Tc(97.907) Rhenium75Re186.207 Bohrium107Bh(262.12) Neodymium60Nd144.24 Uranium92U238.0289 ETALS ETALLOI ONMETA 6B(6) Chromium24Cr51.9961 Molybdenum42Mo95.96 Tungsten74W183.84 Seaborgium106Sg(263.12) Praseodymium59Pr140.9076 Protactinium91Pa231.0388 M M N 5B(5) Vanadium23V50.9415 Niobium41Nb92.9064 Tantalum73Ta180.9488 Dubnium105Db(262.11) Cerium58Ce140.115 Thorium90Th232.0381 4B(4) Titanium22Ti47.867 Zirconium40Zr91.224 Hafnium72Hf178.49 Rutherfordium104Rf(261.11) thanides Actinides Hydrogen11H1.0079,er1A2A(1)(2)er,mBerylliumLithium342LiBe9.01226.941 SodiumMagnesium11123MgNa3B(3)22.989824.3050 ScandiumPotassiumCalcium2119204KCaSc40.07839.098344.9559 YttriumRubidiumStrontium3937385YRbSr85.467887.6288.9059 LanthanumCesiumBarium5557566CsBaLa132.9054137.327138.9055 ActiniumFranciumRadium8987887FrRaAc(227.0278)(223.02)(226.0254) LanNote: Atomic masses are2007 IUPAC values (up tofour decimal places).Numbers in parentheses areatomic masses or massnumbers of the most stableisotope of an element. riodmber oup numbS. systemoup numbPAC syste Penu GrU.GrIU Copyright 2016 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. 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. Copyright 2016 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. 5 REASONS to buy your textbooks and course materials at 1 SAVINGS: Prices up to 75% off, daily coupons, and free shipping on orders over $25 2 CHOICE: Multiple format options including textbook, eBook and eChapter rentals 3 CONVENIENCE: Anytime, anywhere access of eBooks or eChapters via mobile devices 4 SERVICE: Free eBook access while your text ships, and instant access to online homework products 5 STUDY TOOLS: Study tools* for your text, plus writing, research, career and job search resources *availability varies Find your course materials and start saving at: www.cengagebrain.com Source Code: 14M-AA0107 Engaged with you. www.cengage.com Copyright 2016 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. IntroductIon to General, organic, and Biochemistry ElEvEnth Edition Frederick A. Bettelheim William H. Brown Beloit College Mary K. campbell Mount Holyoke College Shawn o. Farrell Olympic Training Center omar J. torres Santa Ana College Australia • Brazil • Mexico • Singapore • United Kingdom • United States Copyright 2016 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. 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. Important Notice: Media content referenced within the product description or the product text may not be available in the eBook version. Copyright 2016 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. Introduction to General, Organic, © 2016, 2013 Cengage Learning and Biochemistry, Eleventh Edition WCN: 02-200-203 Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, ALL RIGHTS RESERVED. No part of this work covered by the copyright herein Omar J. Torres may be reproduced, transmitted, stored, or used in any form or by any means graphic, electronic, or mechanical, including but not limited to photocopying, Product Director: Mary Finch recording, scanning, digitizing, taping, Web distribution, information networks, Product Manager: Maureen Rosener or information storage and retrieval systems, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without the prior Content Developer: Alyssa White written permission of the publisher. Product Assistant: Christopher Robinson Media Developer: Brendan Killion For product information and technology assistance, contact us at Marketing Manager: Julie Schuster Cengage Learning Customer & Sales Support, 1-800-354-9706. Content Project Manager: Teresa L. Trego For permission to use material from this text or product, submit all requests online at www.cengage.com/permissions. Art Director: Maria Epes Further permissions questions can be e-mailed to Manufacturing Planner: Judy Inouye [email protected]. Production Service: Graphic World Inc. Photo Researcher: PreMedia Global Library of Congress Control Number: 2014948100 Text Researcher: PreMedia Global ISBN-13: 978-1-285-86975-9 Copy Editor: Graphic World Inc. ISBN-10: 1-285-86975-3 Text Designer: Diane Beasley Cover Designer: Kathleen Cunningham Cengage Learning Cover Image: Seth Joel/Photodisc/Getty Images 20 Channel Center Street Boston, MA 02210 Compositor: Graphic World Inc. USA Cengage Learning is a leading provider of customized learning solutions with office locations around the globe, including Singapore, the United Kingdom, Australia, Mexico, Brazil, and Japan. Locate your local office at www.cengage.com/global. Cengage Learning products are represented in Canada by Nelson Education, Ltd. To learn more about Cengage Learning Solutions, visit www.cengage.com. Purchase any of our products at your local college store or at our preferred online store www.cengagebrain.com. Printed in the United States of America Print Number: 01 Print Year: 2014 Copyright 2016 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. 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, 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 Copyright 2016 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. Contents in Brief General chemistry chapter 1 Matter, Energy, and Measurement 1 chapter 2 Atoms 27 chapter 3 Chemical Bonds 58 chapter 4 Chemical Reactions 91 chapter 5 Gases, liquids, and Solids 117 chapter 6 Solutions and Colloids 147 chapter 7 Reaction Rates and Chemical Equilibrium 175 chapter 8 Acids and Bases 200 chapter 9 nuclear Chemistry 233 organic chemistry chapter 10 organic Chemistry 260 chapter 11 Alkanes 273 chapter 12 Alkenes and Alkynes 298 chapter 13 Benzene and its derivatives 322 chapter 14 Alcohols, Ethers, and thiols 338 chapter 15 Chirality: the handedness of Molecules 358 chapter 16 Amines 376 chapter 17 Aldehydes and Ketones 389 chapter 18 Carboxylic Acids 404 chapter 19 Carboxylic Anhydrides, Esters, and Amides 423 iivv Copyright 2016 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.