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OtJ9VNI:J :JH3I1/\ISl.tJA , \ 0C19VNI:J :J 3H/\11 1S�CIA SI.XJ. H30.IJ.ION M !LfJJWoe/u/a6a d3\f�SON ------ d1aull;)a H'EIT nd dsaeJp P}Jl!aAaJ ' NraaMJS aOALt7S8 LibraorfCy o ngrCeastsa loging-in-DPautbal ication WadeL,. G . Organcihce mis/tL r.yG .W adeJ,r . p. cm. Includbeisbl iograrpehfiecraelna cnedis n dex. ISBN0 -13-147871-0 I.C hemistOrryg,a nic-TextboolkT.si .t le. QD251.33.3w2006 547-dc22 2004060047 ExecutEidviet oNri:c olFeo lchetti Editor-in-JCohhiCneh fa:l lice Editor-in-DCehvieelfo,p meRnatyM: u llaney DevelopmEednitt oCra:r oPlr itchard-Martinez ExecutMiavnea ginEgd itoKra:t hleSecnh iaparelli AssistMaannta ginEgd itoBre:t Shw eeten ProjeMcatn ageKrr:i sten Kaiser MediEad itoMri:c haJe.lR ichards EditorAisasli stAanngte:l Sai ca ProductEidoint oDro:n naK ing SeniMoarr ketiMnagn ager: SSatretvoer i ManaginEgd itoArV, P roduct&i Moann agemenPta:t riBcuiran s DirecotofCr r eatiSveer vicPeasu:Bl e lfanti ArtD irector/DCeosviegrn Keern:n yB eck InterDieosri gSnu:z annBee hnke AV EditoCro:n niLeo ng ArtS tudiIom:a gineering DirectIomra,g Ree sourCceen teMre:l inRdeao ManageRri,g htasnd P ermissiZoinnsAa:r abia ManageVri,s uRaels earBceht:Bh r enzel ManageCro,v eVri suRaels ear&c Phe rmissiKoanrse:Sn a ntaa r PhotRoe searcher/Plemramgies sCiooonr dinaEtloari:Sn oea res Assistant ManuMfaancatguerMrii:nc gh aBeell l ManufaclUBruiynegrA :la Fni scher CoveIrm ageJ:o sepGha lluc(c2i0o0 4) © 20062,0 031,9 991,9 951,9 911,9 87P earsEodnu catiIonnc,. PearsPorne ntHiaclel PearsEodnu catiIonnc,. UppeSra ddlRei veNrJ,0 7458 Allr ighrtess ervNeod p.a rotft hibso okm ayb e reproduicnea dn,yf ormo rb ya nym eans, withopuetr missiinwo rni tifnrgo tm hep ublisher. PearsPorne ntHiacWe" isa t rademaorfPk e arsEodnu catiIonnc,. Spect©ra S:i gma-AldCroi.c h Printientd h eU niteSdt atoefsA merica 10 9 8 7 6 5 4 3 ISBN 0-13-147871-(0St udeEndti tion) ISBN 0-13-187151-X( ReviCeowp y) PearsEodnu catiLotnd L.,o ndon. PearsEodnu catAiuosnt raPltiyLa.t dS.,y dney PearsEodnu catSiionn gapoPrteeL,.t d. Pearson EduNcoarttiAhos ni Lat dH.,o nKgo ng PearsEodnu catiCoann adIan,c T.,o ronto PearsEodnu cacfdoeMn e xicSo.,A d.e c .Y. PearsEodnu cat-ioJnapaTn,o kyo PearsEodnu catiMoanl aysPitae,L. t d. .1 0 sw:}.Anpau:}. sJeoulplae6nas e :}.ML{!:}.w e:)u0l1a6a BriCeofn tents Prefaxcxei ii 1 IntroducatinodRn e view 2 StructuarnedP ropertoifeO sr ganic Molecules 39 3 StructuarnedS tereochemiosfAt lrkya nes 81 4 The StuodfyC hemicRaela ctio1n2s5 5 Stereochemi1s6t7r y 6 Alkyl HalNiudcelse:o phSiulbisct ituatnidoE nl iminat2i1o2n 7 StructuarnedS yntheosfiA sl kenes 279 8 ReactioonfAs l kenes 321 9 Alkyne3s8 2 10 StructuarnedS yntheosfiA sl coho4l1s7 11 ReactioonfAs l coho4l6s0 12 InfrarSepde ctroscaonpdyM assS pectrome5t0r8y 13 NucleaMra gnetiRce sonanScpee ctrosc5o5p9y 14 EtherEsp,o xideasn,dS ulfid6e2s3 15 ConjugatSeyds temOsr,b itSaylm metrya,n dU ltraviolet Spectrosc6o6p3y 16 AromatiCco mpounds 705 17 ReactioonfAs r omatiCco mpound7s4 9 18 Ketoneasn dA ldehyde8s0 5 19 Amines8 36 20 CarboxyAlciicd 8s7 0 21 CarboxyAlciicdD erivati9v7e8s 22 CondensatiaonndsA lphaS ubstitutoifoC nasr bonyl Compound1s0 41 23 CarbohydraatnedsN ucleAicci d1s0 97 24 AminoA cidsP,e ptidaensd,P rotei1n1s5 3 25 Lipid1s2 00 26 SynthetPiocl ymers 1222 Appendic1e2s4 3 Answertso S electPerdo blemAs 1 Photo CrePdCi1t s Index1 1 vi Contents Prefaxcxei ii Aboutth eA uthoxrl i 1 Introducatnido n Revi1e w 1-1 TheO rigionfsO rganCihce mist1r y 1-2 PrincipolfAe tso miSct ruct3ur e 1-3 BondF ormation:O ctTehRteu le6 1-4 LewiSst ructu7r es 1-5 MultipBloen din8g SummaryC:o mmonB ondinPga tte(rUnnsc harg9e d) 1-6 ElectronegaatnidBv ointdPy o lari9t y 1-7 FormaClh arge1s1 1-8 IoniSct ructu1r2e s Summar:yC ommonB ondinPga tteirnnO sr ganCiocm poundasn dI ons1 3 1-9 Resonan1ce3 1-10S tructural F1or7m ulas 1-11M oleculFaorr mulaansd E mpiriFcoarlm ul2as0 1-12A rrhenAicuisd asn dB ases2 1 1-13B r¢nsted-LAocwirdyas n dB ase2s 2 1-14L ewiAsc idasn dB ase2s 9 Chapt1eGr l ossa3r2y StudPyr oblem3s4 2 StructaunrdeP roperties ofO rganiMco lecul3e9s 2-1 WaveP ropertoifEe lse ctrionnO sr bita3l9s 2-2 MoleculOarrb ita4l1s 2-3 PiB ondin4g4 2-4 HybridizaatnidMo onl eculSahra pe4s5 2-5 DrawinTgh ree-DimensMioolneaclu l4e9s 2-6 General RoufHl yebsr idizaatnidGo eno metr5y0 2-7 BondR otati5o4n 2-8 Isomeri5s6m 2-9 PolaroiftB yo ndasn dM olecul5e8s 2-10I ntermoleFcourlcaer6s 1 2-11P olarEiffteyc tosn S olubili6t5i es 2-12H ydrocarb6o8ns 2-13O rganCiocm poundCso ntainOixnygg en7 1 2-14O rganic Compounds Contain7i3n g Nitrogen Chapt2eGr l ossa7r5y StudPyr oble7ms7 vii viii Contents 3 StructaunrdeS tereochemistry ofA lkane8s1 3-1 ClassificaotfHi yodnr ocarb(oRnesv ie8w)1 3-2 MoleculFaorr muloafsA lkane8s2 3-3 NomenclatoufAr lek ane8s3 SummaryR:u lefso Nra minAgl kane8s8 3-4 PhysicParlo pertofiA elsk ane8s9 3-5 Usesa ndS ourcoefsA lkane9s1 3-6R eactioofnA sl kane9s3 3-7 StructaunrdCe o nformatoifoA nlsk ane9s4 3-8 ConformatoifoB nust an9e8 3-9 ConformatoifoH nisg heArl kane1s0 0 3-10C ycloalka1n0e0s 3-11c is-trans IsionCm yecrliosaml ka1n0e3s 3-12S tabiloiftC iyecsl oalkaRniensgS; t ra1in0 3 3-13C yclohexCaonnef ormati1o0n7s Problem-SolSvtirnagt eDgyr:a winCgh air Conformati1o1n0s 3-14C onformatoifoM nosn osubstiCtyuctleodh exa1n1es1 3-15C onformatoifoD niss ubstiCtyuctleodh exa1n1e4s Problem-SolSvtirnagt egRye:c ognizciinsg andt ranIss ome1r1s6 3-16B icyclic Mol1e1c7ul es Chapt3eG rl ossa1r1y 9 StudPyr oblem1s2 2 4 TheS tudoyf C hemicRaela ctio1n25s 4-1 Introduc1t2io5n 4-2 ChlorinaotfMi eotnh an1e2 5 4-3 TheF ree-RadCihcaailRn e acti1o2n 6 KeyM echanisFmr:e e-dRiacaHla logenat1i2o8n 4-4 EquilibrCiounms taanntdsF reEen erg1y3 0 4-5 EnthalapnydE ntrop1y3 3 4-6 Bond-DissocEinatthiaolnp 1i3es4 4-7 Enthalpy ChianCn hgleosr ina1ti3o5n 4-8 Kinetaincdst heR atEeq uati1o3n 7 4-9 Activation aEnndte hreTge ym peratuDrepee ndence ofR ate1s 39 4-10T ransitSitoant 1es4 0 4-11R ateosfM ultisRteeapc tio1n4s2 4-12T emperatDuerpee ndenocfHe a logenat1i4o3n 4-13S electiivnHi atlyo genat1i4o4n 4-14T heH ammondP ostul1at4e9 Problem-SolSvtirnagt ePgyr:o posiRnega ction Mechanis1m5s1 4-15R adical Inh1i5bi3t ors 4-16R eactiIvnet ermedi1a5t5es SummaryR:e actiIvnet ermedi1a6t0es Chapt4eG rl ossa1r6y 0 StudPyr oble1ms6 3

Description:

For two-semester courses in Organic Chemistry taken primarily by science and pre-health majors. Wade, organized around functional groups, is known for his student-oriented approach--he incorporates problem solving help (features in green), orientation features (in blue), and complete discussions of