Solutions manual [for] Organic chemistry, sixth edition [by] L.G. Wade PDF
Preview Solutions manual [for] Organic chemistry, sixth edition [by] L.G. Wade
I SO8-N(cid:15)E-(cid:15)hL(cid:14)(cid:14)2-9 d3\f(cid:7)SON ---- d1aUHJa H(cid:9)n LUOTN SM ANUAL JaWni llSiiamme k CalifornPioal ytechSntiactU en iversity OR CC HEMISTRY SIXTHE DITION L.G . WaJdre., ".�JL.-':' Prentice Hall 07458 UppSeard RdilveNJe r, AssistEadnitt oCra:r oSlney der ProjMecatn ageKrr:i stKeani ser ExecutEidviet oNri:c oFloel chetti ExecutMiavnea giEndgi toKra:t hleSechni aparelli AssistMaannta giEndgi toBre:c cRai chter ProductEidoint oKra:t hrOy'nN eill SupplemCeonvteM ra nagePra:u Glo urhan SupplemCeonvteD re signJeora:n nAel exandris ManufactBuuryinegrI :l eKnaeh n CoveIrm agCer ediJto:s eGpahl luc(c2i0o0 4) 200P6e arsEodnu catIinocn., PEARSON © PearsPorne ntHiaclel PrenticPee arsEodnu catIinocn., Hall UppeSra ddRliev eNrJ,0 7458 Allr ighrtess ervNeod p.a rotf t hibso okm ayb er eproduicnea dn yf ormo rb ya nym eansw,i thout permisisniw orni tfirnogtm h peu blisher. PearsPorne ntHiaclel i™sa t rademoafrP ke arsEodnu catIinocn., Thea uthaonrd p ublisohfte hrib so okh avues etdh ebiers etf foirntp sr epartihnibgso okT.h eseef forts inclutdhee d evelopmreenste,a racnhd,t estionftg h et heoriaensdp rogratmosd etermitnhee ir effectivTehneae ustsh.ao nrdp ublismhaekren ow arraonfta yn yk inedx,p resosrie mdp liweidtr,he gatrod thesper ograomrts h ed ocumentactoinotna iinnte hdi bso okT.h ea uthaonrdp ublisshheanrlo ltb el iable ina nye venfto irn cideonrtc aoln sequednatmiaaglie nsc onnectwiiotnoh r,a risoiuntogf t,h feu rnishing, performaonruc seeo, f t hepsre ograms. Thisw orki sp rotectbeydU niteSdt atecso pyriglhatw sa ndi sp rovidseodl efloyr t eachicnogu rsaensd assesssitnugd enlte arniDnigs.s eminatoiros na loef a nyp arotf t hiwso rk( includoinnt gh eW orldW ide Web)w ildle strotyh ei ntegroiftt yh ew orka ndi sn otp ermittTehde.w orka ndm aterifarlosm i ts hould neverb e made availabelxec epbty instructuosrisn tgh ea ccompanyitnegx ti nt heicrl asseAsl.l recipieonftt sh iwso rka ree xpectteoda bidbey t hesree strictainodtn osh onort hei ntendpeedd agogical purposaensd t hen eedosf o theirn strucwthoorr se loyn t hesmea terials. Printiendt heU niteSdt atoefsA merica 10 9 8 7 6 5 ISBN 0-13-147882-6 PearsEodnu catLitodnL. o,n don PearsEodnu catAiuosnt raPltiyLa.t dS.y,d ney PearsEodnu catSiionng apPotreeL.,t d. PearsEodnu catNioorntA hs iLat dH.o,n Kgo ng PearsEodnu catCiaonna dIan,c T.o,r onto PearsEodnu cacdie6M ne xicSo.,Ad .e PearsEodnu cation-JTaopkayno, c .y. PearsEodnu catMiaolna ysPitaeL,.t d. TABLE CONTENTS OF Prefa...c..e... ................................................................................................................................v Symbolasn dA bbreviat.i.o.n.s. .................................v.i.i. ............................................................. Chapt1er IntroducatnidRo env ie..w... ................................................................................. 1 Chapt2e r StructaunrdeP ropertoifOe rsg anMiocl ecul...e..s... ..........................................2 5 Chapt3e r Structure and SteroefAo lckhaenm.e.i..s.s.. t...r...y... ..........................................4 5 Chapt4e r TheS tudoyf C hemicRaela cti.o...n...s.. ............................................................. 59 Chapt5e r Stereochem..i...s...t..r...y... ................................................................................. 79 Chapt6e r AlkyHla lideNsu:c leophSiulbisct ituatnidEo lni minat...i...o..n... ..................... 99 Chapt7e r Structure and oSfAy lnktehne.es...si...s .. .........................................................1 35 Chapt8e r ReactioofnAs l ken.e..s... ................................................................................. 159 Chapt9e r Alkyne...s.. ...................................................................................................... 191 Chapt1e0r StructaunrdeS yntheosfiA sl coho...l...s.. .........................................................2 11 Chapt1e1r ReactioofnA sl coho...l..s... .............................................................................. 229 Chapt1e2r InfraSrpede ctrosacnodpM ya ssS pectrom..e..t...r..y... ..................................... 259 Chapt1e3r NucleMaarg netRiecs onanScpee ctros.c...o..p...y... ......................................... 271 Chapt1e4r EtherEsp,o xidaensd,S ulfi.d...e...s.. ................................................................ 299 Chapt1er5 Conjugated SyOsrtbeimtSsay,lm metrayn,dU ltraviSopleectt ros.c...o...p..y... 317 Chapt1e6r AromatCiocm poun.d..s... ................................................................................3 41 Chapt1e7r Reactions of CAormopmoautni.dc..s. .. ............................................................ 365 Chapt1e8r Ketonaensd A ldehyd..e...s.. ............................................................................4 01 Chapt1e9r Amine.s... ......................................................................................................4.. 39 Chapt2e0r Carboxylic ...A...c...i..d...s.. .............................................................................4 69 Chapt2e1r CarboxyAlciicdD erivat..i..v...e...s.. ................................................................4 99 Chapt2e2r CondensatainodnA sl phSau bstituotfiC oanrsb onCyolm pound..s... ............... 537 Chapt2e3r CarbohydraantdeN su cleAicci d..s.. ................................................................ 585 Chapt2e4r AminoA cidsP,e ptidaensdP, r ote.i..n...s... ...................................................... 617 Chapt2e5r Lipi.d..s... ........................................................................................................ 645 Chapt2e6r SynthePtoilcy me.r...s... ...................................................................................6 59 Appendix Summaroyf I UPACN omencla.t..u...r...e.. .......................................................6 75 I: Append2i:x Summaroyf A cidiatnyd B asic.i..t....y.. ........................................................... 689 iii PREFACE HintfsoP ra ssing OCrhgeamniisct ry Do youw antt op asyso urc oursieno rgancihce mistrHye?r ei sm y besatd vicbea,s eodn o ver thiryteya rosfo bservisntgu denltesa rnionrgg ancihce mistry: Hin#t1 : Its eemsst raigrhwatfrodb,u th uman,si ncludsitnugd esn,tt rtyo t ake thee aswy ay ouDtuo nt thitpelhr eodyib slceomvtseh.re riesn os hort-cUuntl.e syso uh avea measurIeQda bov2e 00 andc omfortacbrluyi isnet het op1 ofy ourc lasdso,t hpero blemUss.u alyloyu tre ach(eprr ofesosr or % teachiansgs istwainltrl)e commencde rtaoinne st;r yt od oa llth osree commendeIdfy. o ud oh aloff themy,o uw illb eh alf-prepaattr eestdti me(.D o youw anty ours urgecoonm intgo y oura ppendectomy havinpgr actiocneldhy al/thper ocedurAen?d)w heny oud ot hep roblemkse,e pt hiSso lutiMoannsu al CLOSED.A void looaktim nyg a nswer beyfoouwr rei tyoe uran swery-our traynidns gt rugglwiintgh thep robleimst hem ostv aluabplaero tf t hep robleDmi.s coveirsay m ajopra rotf l earniRnegm.e mber thatth ep rimagroya olf d ointgh ese proibsln eomjtsu sgte ttitnhger ighatn swebru,tu nderstantdhien g materiwaell l enotuogg ehtr ighatn swetrost heq uestiyoonush aven't yseete.n Hin#t2 : Keeupp . Gettibnegh inidny ouwr orki na c oursteh amto vesa sq uickalsyt his iosn e theK isosf D eathF.o rm osts tudenotrsg,a ncihce misitsrt yh em ostr igorous intcehlallelcettnuhgaeely havef acesdo f ari nt heisrt ud.i eSsomea ret akebny s urpraitst eh ed iligeintrc eeq uirDeosn.' tth ink thayto uc ans tudayl olf t hem ateritahlec ouploefd aybs eforteh ee xam- welly,o uc anb,u ty ouw on't passS.t udoyr gancihce mistlriyka e f oreilgann guagter:yt od os ome evdearyys ot hatth ef reshly trainneedu rosntsa syh arp. Hin#t3 :G eth wheyno u Usey ourt eacheorf'fsi hcoeu rwsh eny ouh aved ifficulty. elp neeidt . Manys chools have tuto(riiwnnh gi ccoher ngtaenrcishc e misitsra y p opuloafrf erinHge)r.e 'as s ecret: absoluttehleby e swta yt oc ementth imsa teriianyl o urb raiinst og ett ogethweirta hf ewo fy oufre llow studenatnsdm akeu p problefmosr e acho thetrh,e nc orreacntd d iscutshse m.W heny ouw ritteh e probleymosu,w ilgla ignr eaitn sigihnttw oh att hiissa lalb out. Purpoosfte h iSso lutiMoannsu al Sow hati st hep oinotf t hiSso lutiMoannsu alF?i rsItc ,a n'dto y ours tudyifnogr yoSue.c ond, sincIea m notl eanionvge yro urs houldaesyr o uw rityeo uar nswerIsc ,a n'gti vyeo ud irefcete dbaocnk whaty ouw ritaen dt hink-tphrei nt mediislu imm itiendi tuss efulneWshsa.t I cand of ory oui s: provicdoer rect antshwepe urbsl;i shPerrosf,e sWsaodre ,P rofesKsaonrt orow(smkyir eviewearn)d, I) Ih aveg onet og realte ngtthosa ssutrhea wth atIh avew rittiescn o rrefcotrw, e aluln dersthaonwdi tc an shakae s tudencto'nsf idetnocd ei scovtehrat th ea nswebroo kf lubbuepd; 2 )pr oviad ceo nsiderable degreoef r igobre;y ontdh ef undamental reqoufic roermreenctt nIe hsasv,et rietdof lesohu tt hese answerbse,i ncgo mplebtuets uccin3ct)p;r oviidnes igihntth oo wt os olvae p robleamn di ntwoh eret he sticiknyt ellepcotiunaatlrs e .I nsigihstt h et oughetsoat c complibsuhto, v etrh ey earIsh ,a vec omet o understwahnedr set udenhtasv et roubsloeI ,h avet rietdoa nticipyaoutreq uestiaonndst oa dde nough detasiolt hatth e concaeswp etl,al s t hea nsweirsc, l ear. Iti sd ifficfuolrst t udenttous n derstoarna dc knowletdhgaett h eir teaacrhehe urmsa n( somaer e moreh umant hano thersS)i.n cIe a m human( despwihtaet m y studenmtisg hrte porIt c)a,n a ndd o makem istakeIsft. h eraer em istakienst hibso okt,h eayr em y solree sponsibainldiI ta ym, s orryI.f youf inodn eP,L EASEl emte knows ot haittc anb ec orrecitnef du tuprrei ntinNgispi. ti nt heb ud. What'Nse wi nt hiesd ition? Bettaenrs wersP!a rotf m y goailn t hiesd itihoansb eent oa ddm oree xplanatmoartye rial to clarihfoyw t oa rriavtet hea nswerT.h ep ossibiolfim toyr et hano nea nswetro a problehma sb een noted.Th e IUPANCo menclatauprpee ndhiaxs b eene xpandetdo i nclubdiec yclihcest,e roatom replacemeanntdts h,eC ahn-Indg-oPlrelsoygs teomfs tereochedmeisciagln ation. Bettgerra phicTsh!e p rinmte diumi sv eryl imitiendi tasb ilittocy o nvetyh ree-dimensional structiu�froarlm atiao pnr,obletmh ahta sp laguoerdg ancihce misftosro vera centurIy h.a vea dded . someg raphicCrSe atedth es oftwaCrhee,m 3D®t,o t rtyo s howa tomisn s pacweh erteh aitn formation 1I1 isa keyp arotf t hes olutioInn.d rawinNgM R spectrreap,r esentaltiinodenr aalw inhgasv er eplaced rudimentaatrtye mpattds r awinpega kfsr omp revioeudsi tions. Bettjeork esT?o om ucht oh opef or. v SomeW eb Stuff Prenticem-aHianltla ai wnseb sitdee dicattoet dh eW adet extt:r wyw w.prenhall.com/wade. Twoe ssentwieba sli tperso vidsipnegc tarrael istoendt heb ottoomfp .2 70. Acknowledgments No projeocftt h issc opiese vedro nea loneT.h esaer et eame fforatnsdt, h eraer es everpaelo ple who havea ssisatnedd faciliinot naetf eads hioorna nothwehro desermvye t hanks. ProfessLo.Gr . Wade,J r.y,o urt extbook aiusta h roerm,a rkabpleer sonH.e hasg onet o extraordilneanrgytt hosm ake ttheex tboaoskc leaorr,g aniziendf,o rmatainvdie n sighatsfp uols sible. Heh ass oliciatnedfd o llowmeyd s uggestioonhn isst exatn,d h isc ommentosn m y solutihoanvseb een perceptainvdev aluablWee. agreeeda rloyn thaotu rp rimargyo ali st oh elpt hes tudenltesa ran fascinaatnidnc gh allengsiunbgj eacntd,a lolf o ure fforhtasv eb eend irectteodw artdh agto alI.h ave apprecioautrec do llaboration. My newc olleagDure.E, r iKca ntorowshkaisr, e vieedwt hee ntimraen uscrfioprat c curaacnyd styleH.i sd iligenactet,e nttiood ne taainld c hemicwails domh avem adet hias b ettmearn ualE.r ic stanodnst hes houldoefrp sr evioruesv iewwerhos s coureeadr lieedri tifoonrse rrorJse:s siGcial man, Dr.K ristMeeni senheiamnedrD ,r .D anM atterMnr.. R ichaKridn gh aso fferneudm eroussu ggestions onh owt oc larimfuyr kye xplanatiIoa nms g.r atetfout lh ema ll. Thep eoplaet P rentice-hHaavleml a det hipsr ojepcots siblGeo.o db ooksw ouldn ote xist without dtehdeiicra tpiroonf,e ssionaanldie sxmp,e rienAcmeo.n gt hem anyp eoplweh o contributed are:L eeE nglandwehro, c onnectmeed w itthh ipsr ojeNcitc;o lFeo 1chetti, AdvancedE diCthoerm;i stry andK ristKeani saenr dC arolSen ydePrr,o jeMcatn agers. Thee ntimraen uscrwiapstp roducuesdi nCgh emDrawth®e,r e markabsolfet wafroerd rawing chemicsatlr uctduerveesl opbeydC ambridgeCSoorfptC. a,m bridge, We,t heu serosfs ophisticated MA. softwalriek Ceh emDrawa,r et heb eneficioafrt iheeis n telligaenndcc ree atiovfit thye p eoplient he computienrd ustWrey .a ref ortuntahtaett h eayr es os mart. Finallya,p precimayt fer ienwdhso s upportmeed t hroughtohuitps r ojemcots,t n otabmlyy I good froifea nldm ost forty yeLaarnsg,.T heJs utduyd enatrset oon umeroutsol isbtu,ti ti sf ort hem thaatl tlh ihsa ppens. JanW illiaSmi mek DepartmoefnC th emistarnydB iochemistry CalP olSyt atUen iversity SanL uiOsb ispCoA, 93407 Emailj:s [email protected] DEDICATION Tom y inspiratcihoenmails try teachers: JoeP laskwahos m,a det heb atter; KutrK afmuan,w ho baketdh ec ake; CarDlj era,ws hso iputo nt hei cing; andt om y parents: Ervina ndI milBd.Sa i emk, J. whoh adt heo rigicnoanlc ept. vi SYMBOLSA NDA BBREIVAT IONS Bleoiawsl iossfyt m abnaodbl bsr uesveitdahSt iuoiistlno Mi naoslnnc ,usosa inwsitttehhunos tsie end thteex btWyba o.d(o eDnkooe tx apoletflch ttem osa seke etny oson euo. Y w owulil letarnh em throyuosguthrouoo fdur ytgc ahneimci stry.) BONDS as ibnognlde ad oubbolned at rbiopnlde ab ointndh d riemee cnosmoiiuoonttfnghp s ea,t p oewtrahr reed a der - ab ointndh d rmieeieno, gsn osbienhtgihp neaad pw efarryt o hrmee ader 111111111111 as trbeot,inc tndhhp eerd oo cffeo srmiosnbre gr a king ARROWS ianr easchtdoiiworsnfe ,rcr otemia tocpontr aondtusc ts - sigenqiufii(ltenti sboobc e ro inwufimurt sehes do nance) sigrneisfo(inntebaooscent o c newf iuetsqheu di librium) .. .. shdoiwrsoe efcl temicvootenrm: o enn t thaer rowwiohtnbeheaa s rdhb mo owmvsnee otof ne el ectron; the awritrtwbohoaw s rhhbemosaow dvs e oamfp e aonieftcrl t erons shpoowlsoa afbr oionmtrdoy l teahceru rlosewi,hg entaihmdfeon y reiegn eagnot tdfih vee dilpeo SUBSTTUIEGNORTUP S Me am etghryoClu3H p , Et aent hyCl2HC 3Hg roup, Pr ap rgorppoay,tu l h craergebr (ootnupw poo sa srirmbaelnnegt es) Bu ab ugtryaolf u ocpua,rrg br(oofnupo pou sarsrr iabnlgee ments) R thgee naebrbarfleao vanril agktry(iolaouo nrpnsy u bstintouutnse dcnertru tgirnoyu)p Ph ap hegnryolu po,afb ethnrezia enassnng uae bm esr teipttreuedes:ne tn, or < » 0- Ar thgeerl nna eafmoear r oagmnra otuipc coinnotunnee pdxa tg e vii SymabnAodbl bsr ecvoinattiinounesd, SUSBTITGUOREUNPcTSo ,n tinued oI I Ac aanc gertoyCulHp -3:C- Cy a cygcrloouhpe:x yl 0- o Ts toospry- lt,ol lfugoernnoyCeulH�sp 3 u: S- "==1- oII o II Bco at -brubtgoornx(oyyauclmapa i caninpodde pcthiedme(i Cs)Ht-33r0Cy C)--: orac arbo(bbeennzzoyxglyro(o xauymapcic aanirnpdobde o pcnthyieldm)ei st0r y): Cbz Z, < C2H-)-0-g- REGAENATNSSD O LVENTS DCCd icxycycallrobhoediimNi=Cd=eN o- -Q DMSdOi methylsoI Iu lfoxide S ....... ' H3CC H3 ehterde itehtyChlHCe 3Hr,22C 0HC3H Cl 0 MCBPAm eta-chlaocr;odp erg-o x0yO -hHe nzo;c < > metvhikynelyt lo no e g MVK H3C� ....... NSB -bronmiomOsiudcec iO �N N I Br coinnotune pdna egxet viii SymabnAodbl bsr ecvtoiinantuieodn s, REEANGATNSS DLO VESNc,Toi nntued PCC pyricdhilnoiruoCmcr3 ·h0H rCoNIm ate, � ') • C3HH H C3HH I I I I I Sai2BdHi siamyHl-Cb-oCr-anBe- C-C-H I I I I C3HC 3H C3HC 3H THF tetrahydrofuran o SEPCTCRPOOYS IR infsrpaserccetodrp oy NMR nucmlaeegtranioercns asnptcereco scopy MS masspse cyt rometr UV ultrscaprvtesooicpoyl et ppm papremtris l aul niueiosidtnNn ,M R Hz hecryetpcszesl ,cre o ,nu tdnao fi fer quency MHz megamhielorlcftiye zopcs,nesl sre cond TMS tetranme(e,C3)4tS H,hti yhrleeesf nciecolrema piNonMu Rn d sd,t,q , s indgolutebrltltieq,e,pu t ar,rte enfttgeo, r rithopefe aanNnukM msaRb b esrog ripvteiso n nm noamnetmeerts(e,ur suussaa easlud lno ywif at v elength) 10-9 mJz mass-rtaoitm-niac soshp,tsae r rcogmee try iNnMR c,eh mischviaaflmlt eu aeis,pnu p rme d 8 wavelength A ferqcuye n v OTHER ax(iciahnlfa oiormrcfs y clohexane) a, ax euqat(ocirihnfaa olior rcfm y sc lohexane) e,e q higohcpecimsuelotcdel u oarrb ital HOMO louwnespoticm ecodul oercbuiltaarl LUMO nroe action NR (poosanian tr ioormniasnt gi)c m,p arthmae,t paa,r a 0, whweritnteo nvae nr a"rhrewoahwwter:"ni b; t etafle oenrt" etc ehiran:n" g e paprtoisacilht apirtavlginre eae ,gc ahtairvgee eenrfgreyol tmer gconimrecaat d(ilaitgihotn) spercoitafattithD clie ioo snnfoe d (8i5n9um m) ix
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