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Chem2213ExamPackageSolutionsDec2013.pdf

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Department
Chemistry
Course
Chemistry 2223B
Professor
James Wisner
Semester
Winter

Description
Chem2213FinalExamSolutions2012201120102009Prep1012012FinalExamAnswers1 DAllatomsaresp3fourVSEPRgroupsaroundeachatom2 DIthas9unitsofunsaturation3 BThehighestpHwillbethemostalkalinesolutionmostbasicsoyouarelookingfortheleaststablebaseAnionsaremorebasicthanneutralmoleculesandtheonlyanionicmoleculeisB4 CThisiscistransinaringnotadoublebondsotherehavetobetwocarbonatomswithonehavecistransgeometrypossibleinaringfunctionalgroupeachatleastto5 EThereare3isomerswitha5memberedringOneisa5carbonringwithanalcoholcomingoffandtheothertwoare5memberedringscontaining4carbonsand1oxygenwithamethyldifferentplacesmethylcancomeoffsotherearetwoisomerslikethisgroupcomingofftwo6 DMesocompoundscontainchiralcentersbuthaveamirrorplaneinthemoleculeThesecondandthirdcompoundsaremesochoicestoAorBTakeaperspective7 AIfyoufigureout1and3firstyoucannarrowdownyourandredraw2tomakeiteasiertoassign8 ETheyarediastereomersbecausethefrontchiralcentersareindifferentconfigurationsbutthebackonesarethesame9 ANucleophilicadditiontoaldehydesandketonescanresultinachiralcarbonbecausetheproductissp3hybridizedatcarbonandelectrophilicalkeneadditionalsoresultsinansp3hybridizedcarbonproductTheothertwoaresp2hybridizedatcarbonintheproductsocantbechiraluponeitherendofthealkene10 EAmixtureofregioisomersmeansthattheatomswillendwithoutanyselectivitybutweknowthatmanyadditionreactionsthatgothroughcarbocationshaveMarkovnikovselectivityandthehydroborationoxidationhasantiMarkovnikov11 DThefirstthreereactionswillhave50yieldoftheproductshownbecausetheapproachothersideofthealkeneisntshownforanyofthemDwillactuallyhaveFOURfromtheproductsbecausetheClcouldenduponeitherofthetwosecondarycarbonatomsregioisomersanditcouldcomefromthefrontandbackofeitherofthesecondarycarbocationintermediatesstereoisomersSothatreactionhasapproximately25yieldoftheproductshown12 AC6H6hasfourdegreesofunsaturationbutthedecolourizationof3molesofbrominemeansithastohavethreedoublebondsthatarenotconjugatedotherwiseitisaromaticandwontreactwithjustbromineThebestleavinggroupsarethemostelectronegativeatomsontheperiodictableAfterthat13 Aresonancehelpstostabilizethechargeonaleavinggroupandtheworstleavinggroupisananiononnitrogenbecausenitrogenisnotveryelectronegativesoitisveryunstabletworeactionsshowstrongnucleophilesandsecondaryandprimarysubstratesso14 AThefirsttheylllikelyundergoSN2mechanismsThethirdisatertiarybenzylicleavinggroupandaweakbasesuggestingSN1OnlySN2reactionswillhavefasterrateswithincreasednucleophileconcentrationbecausetheyarebimolecularChem2213FinalExamSolutions2012201120102009Prep10115 AFirstofalltwodifferentlocationsforthealkenesarepossible2hexeneand3hexeneSeconddrawaNewmanprojectionforeacheliminationtoshowthattherearetwoconfigurationsthatgiveHantiperiplanartoBrThisgivesthecisandtransproductsofthetworegioisomersofthealkenessoyouhavefourtotalproducts16 EThemostsubstitutedalkeneisalmostalwaysfavouredineliminationreactionsAlsononeoftheotheranswersmakeanysensewithrespecttotheoutcomeofthereaction DThesmallbaseinAwillyieldtwoalkeneisomersandasubstitutionproductBwillgive217and3hexeneinequalamountsCwillgive2hexeneandthesubstitutionproductsmallbaseEwillonlygive1hexeneDwillgive1hexeneand2hexenebut2hexeneisthemajorproductbecauseitismorehighlysubstituted18 EToturnethanolintoabetternucleophileyouneedtoremoveaprotonandmakeoxygenhappenstoanionicOnlyastrongbasecandothissotheamineanionisthebesttouseItalsobetheONLYbaseintheoptions19 AThefirstreactionandthethirdreaction20 EInordertoeliminateanalcoholweneedtomakeitintoabetterleavinggroupandthatiswhattheprotonfromtheacidwilldoFirstyouformanepoxidethenyouopenitwithsulfurYoudidntgetmuchdetailabout21 Bepoxideopeninginyourlecturenotesunderbasicconditionsbutintheseconditionsyouwillselectivelyhavethesulfurnucleophileaddtothelesshinderedcarbonatom22 ANatomin1willbesp2hybridizedinordertomakethemoleculearomatic23 EThe24 DThemethylgroupisinthewrongplace25 BThealkylamineismorebasicthanthearomaticoneIthassixunitsofunsaturationThreeattachedtonitrogenintheringandtheoneleadingfromthestereocentresistruethetworingtothearomaticringThecarbonNMRwouldhave11signalseverycarbonatomisunique26 DTheprimaryamineslonepairattacksthecarbonattachedtoiodineclosestheringandtheaprotonfromthethenpositivelychargednitrogenatomsodiumhydroxidetakes27 AThisformulahasoneunitofunsaturationandtheIRspectrumshowsaCO28 EThisisanotherwayofsayingthethreecarbonatomshavedifferentenvironments29 CThereisamirrorplanestraightdownthemoleculeverticallysotherewillbeonesignalfortheCH3sonefortheCHsonefortheCH2sandonefortheNHintheHNMRandtherewillbeNMRonesignalfortheCH3sonefortheCHsandonefortheCH2sintheC30 DOneunitofunsaturationPeaksthatintegrateformultiplesof3representmethylgroupsIfitismorethan3thereareequivalentmethylgroups9meansthereare3equivalentmethylACgroupsAKAatertbutylgroupTheotherpeakcomesfromthecarbonylsmethylgroupandEwouldhavemorethan2signals31 E2unitsofunsaturationcantbeB3signalsintheprotonspectrum3uniquekindsofHatomscantbeACorDsoitmustbeEThe6HtripletistheCH3groupsontheendsThe4HquartetaretheCH2groupsnexttotheCH3groupsandthe2HsingletistheCH2inthecenter
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