Table Of Content

solom_fm_i-xxxiv-hr2.qxd 14-10-2009 17:19 Page xxxiv solom_ep_F01-F02v1.qxd 2-10-2009 12:00 Page 2 SOLOMONS 18VIIIA 2 HeHelium4.0026 10 NeNeon20.180 18 ArArgon39.948 36 KrKrypton83.798 54 XeXeno131.29 86 RnRadon(222) m 17VIIA 9 FFluorine18.998 17 ClChlorine35.453 35 BrBromine79.904 53 IIodine126.90 85 AtAstatine(210) 71 LuLutetium174.97 103 Lrawrenciu(262) L 16VIA 8 OOxygen15.999 16 SSulfur32.065 34 SeSelenium78.96 52 TeTellurium127.60 84 PoPolonium(209) 70 YbYtterbium173.04 102 NoNobelium(259) 15VA 7 NNitrogen14.007 15 Phosphorus30.974 33 AsArsenic74.922 51 SbAntimony121.76 83 BiBismuth208.98 69 TmThulium168.93 101 Mdendelevium(258) P M 14IVA 6 CCarbon12.011 14 SiSilicon28.086 32 GeGermanium72.64 50 SnTin118.71 82 PbLead207.2 114 Uuq (289) 68 ErErbium167.26 100 FmFermium(257) TS 13IIIA 5 BBoron10.811 13 AlAluminum26.982 31 GaGallium69.723 49 InIndium114.82 81 TlThallium204.38 67 HoHolmium164.93 99 EsEinsteinium(252) EELEMEN :ommendations:group notation 1112IBIIB 3029 CuZnCopperZinc63.54665.409 4847 AgCdSilverCadmium107.87112.41 8079 AuHgGoldMercury196.97200.59 112111 UuuUub (272)(285) 6566 TbDyTerbiumDysprosium158.93162.50 9798 BkCfBerkeliumCalifornium(247)(251) H ece OFT IUPAC rcts Servic 10VIIIB 28 NiNickel58.693 46 PdPalladium106.42 78 PtPlatinum195.08 110 Uun (281) 64 GdGadolinium157.25 96 CmCurium(247) BLE al Abstra 9VIIIB 27 CoCobalt58.933 45 RhRhodium102.91 77 IrIridium192.22 109 MtMeitnerium(268) 63 EuEuropium151.96 95 AmAmericium(243) A c TC Chemi 8VIIIB 26 FeIron55.845 44 RuRuthenium101.07 76 OsOsmium190.23 108 HsHassium(277) 62 SmSamarium150.36 94 PuPlutonium(244) PERIODI :Atomic number6 C:Symbol :Name (IUPAC) Carbon:Atomic mass 12.011 5467VBIVBVIBVIIB 24252223 MnTiVCrManganeseTitaniumVanadiumChromium54.93847.86750.94251.996 42434041 TcZrNbMoTechnetiumZirconiumNiobiumMolybdenum(98)91.22492.90695.94 74757273 ReHfTaWRheniumHafniumTantalumTungsten186.21183.84178.49180.95 106107104105 BhSgRfDbBohriumSeaborgiumDubniumRutherfordium(264)(266)(262)(261) 58596061 CePrNdPmCeriumNeodymiumPromethiumPraseodymium140.12140.91144.24(145) 90919293 ThPaUNpThoriumProtactiniumUraniumNeptunium232.04231.04238.03(237) 3IIIB 21 ScScandium44.956 39 YYttrium88.906 57 *LaLanthanum138.91 89 #AcActinium(227) e Series e Series 2IIA 4 BeBerylium9.0122 12 MgMagnesium24.305 20 CaCalcium40.078 38 SrStrontium87.62 56 BaBarium137.33 88 RaRadium(226) Lanthanid # Actinid * 1IA 1 HHydrogen1.0079 3 LILithium6.941 11 NaSodium22,990 19 KPotassium39.098 37 RbRubidium85.468 55 CsCaesium132.91 87 FrFrancium(223) solom_ep_F01-F02v1.qxd 2-10-2009 12:00 Page 3 SOLOMONS Relative Strength of Selected Acids and Their Conjugate Bases TABLE 3.1 Conjugate Acid Approximate pK Base a Strongest acid HSbF (cid:3)(cid:2)12 SbF (cid:2) Weakest base 6 6 HI (cid:2)10 I(cid:2) H SO (cid:2)9 HSO (cid:2) 2 4 4 HBr (cid:2)9 Br(cid:2) HCl (cid:2)7 Cl(cid:2) C H SO H (cid:2)6.5 C H SO (cid:2) 6 5 3 6 5 3 (cid:4) (CH3)2OH (cid:4) (cid:2)3.8 (CH3)2O (CH3)2C"OH (cid:2)2.9 (CH3)2C"O (cid:4) CH3OH2 (cid:2)2.5 CH3OH H O(cid:4) (cid:2)1.74 H O 3 2 HNO (cid:2)1.4 NO (cid:2) 3 3 CF3CO2H 0.18 CF3CO2(cid:2) Inc gth HF 3.2 F(cid:2) rea creasing acid stren CCCHCNHHH662HHC334O55CC(cid:4)CNOO3OH2C32HH(cid:4)H2COCH3 444699......0272635135 CCCHCNHCHH66HHO33355CC3CNOO(cid:2)OH2H2(cid:2)2C(cid:2)OCH3 sing base strength n (cid:2) I C H OH 9.9 C H O 6 5 6 5 HCO (cid:2) 10.2 CO 2(cid:2) 3 3 (cid:4) CH NH 10.6 CH NH 3 3 3 2 (cid:2) H O 15.7 OH 2 (cid:2) CH CH OH 16 CH CH O 3 2 3 2 (cid:2) (CH ) COH 18 (CH ) CO 33 33 (cid:2) CH COCH 19.2 CH COCH 3 3 2 3 HC#CH 25 HC#C(cid:2) (cid:2) H 35 H 2 (cid:2) NH 38 NH 3 2 CH "CH 44 CH "CH(cid:2) 2 2 2 (cid:2) Weakest acid CH CH 50 CH CH Strongest base 3 3 3 2 solom_fm_i-xxxiv-hr2.qxd 14-10-2009 17:19 Page i This online teaching and learning environment integrates the entire digital textbook with the most effective instructor and student resources (cid:87)(cid:82)(cid:3)(cid:192)(cid:87)(cid:3)(cid:72)(cid:89)(cid:72)(cid:85)(cid:92)(cid:3)(cid:79)(cid:72)(cid:68)(cid:85)(cid:81)(cid:76)(cid:81)(cid:74)(cid:3)(cid:86)(cid:87)(cid:92)(cid:79)(cid:72)(cid:17) With WileyPLUS: (cid:135) Students achieve concept (cid:135) Instructors personalize and manage mastery in a rich, their course more effectively with structured environment assessment, assignments, grade that’s available 24/7 tracking, and more manage time better (cid:135) study smarter (cid:135)(cid:3) save money (cid:135) From multiple study paths, to self-assessment, to a wealth of interactive visual and audio resources, WileyPLUS gives you everything you need to personalize the teaching and learning experience. »Find out how to MAKE IT YOURS » www.wileyplus.com solom_fm_i-xxxiv-hr2.qxd 14-10-2009 17:19 Page ii ALL THE HELP, RESOURCES, AND PERSONAL SUPPORT YOU AND YOUR STUDENTS NEED! 2-Minute Tutorials and all Student support from an Collaborate with your colleagues, of the resources you & your experienced student user find a mentor, attend virtual and live students need to get started Ask your local representative events, and view resources www.wileyplus.com/firstday for details! www.WhereFacultyConnect.com Pre-loaded, ready-to-use Technical Support 24/7 Your WileyPLUS assignments and presentations FAQs, online chat, Account Manager www.wiley.com/college/quickstart and phone support Training and implementation support www.wileyplus.com/support www.wileyplus.com/accountmanager MAKE IT YOURS! solom_fm_i-xxxiv-hr2.qxd 16-10-2009 11:47 Page iii TENTH EDITION Organic Chemistry solom_fm_i-xxxiv-hr2.qxd 14-10-2009 17:19 Page iv solom_fm_i-xxxiv-hr2.qxd 16-10-2009 12:22 Page v TENTH EDITION Organic Chemistry T.W. GRAHAM SOLOMONS University of South Florida CRAIG B. FRYHLE Paciﬁc Lutheran University JOHN WILEY & SONS, INC. solom_fm_i-xxxiv-hr2.qxd 14-10-2009 17:19 Page vi In memory of my beloved son, John Allen Solomons, TWGS To Deanna, in the year of our 25th anniversary. CBF ASSOCIATE PUBLISHER Petra Recter PROJECT EDITOR Jennifer Yee MARKETING MANAGER Kristine Ruff SENIOR PRODUCTION EDITOR Elizabeth Swain SENIOR DESIGNER Madelyn Lesure SENIOR MEDIA EDITOR Thomas Kulesa SENIOR ILLUSTRATION EDITOR Sandra Rigby SENIOR PHOTO EDITOR Lisa Gee COVER DESIGNER Carole Anson COVER IMAGE ©Don Paulson COVER MOLECULAR ART Norm Christiansen This book was set in 10/12 Times Roman by Preparé and printed and bound by Courier Kendallville. The cover was printed by Courier Kendallville. This book is printed on acid-free paper. Copyright ©2011, 2008, 2004, 2000 John Wiley & Sons, Inc. All rights reserved. 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