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Transcript
CHE312 EXAM1KEY(Ch.16-19) AnswersinBOLDRED MultipleChoice(60%;2%each) PleasemarktheletteroftheBESTanswerforeachquestionclearlyonyouranswersheet.Thankyou! 1. Ethersolubilityinwaterismostlikethatof__________________ofsimilarmolecularweight. A.alkanes B.alcohols C.alkenes D.aromatichydrocarbons 2. WilliamsonEtherSynthesisisbestperformedbyreacting A.analcoholwithdilutewarmacidB.thealkoxideofaprimaryalcoholwithanyalkylhalide C.anyalkoxidewithaprimaryalkylhalideD.twoalcoholswithdilutewarmacid 3. Ethercleavageisareactionoftencarriedoutusingconcentrated A.H2SO4 B.HBr C.HF 4. SharplessEpoxidationisnotablebecauseofitsenantiospecificsynthesisofepoxidesfrom A.alkenes B.allylicalcohols C.cyclicalkenes D.benzylicalcohols 5. Ifwereacttheepoxidefrom1-butene+CH3COOOHwithsodiummethoxide(CH3O–Na+)themainproductis: A.2-methoxy-2-butanol B.2-methoxy-1-butanol C.1-methoxy-2-butanol D.1-methoxy-1-butanol 6. IfItakethesameepoxideusedinquestion5andtreatitwithacidicmethanolsolution,themainproductis: A.2-methoxy-2-butanol B.2-methoxy-1-butanol C.1-methoxy-2-butanol D.1-methoxy-1-butanol 7. Isopropylmethylketoneisthefunctionalclassnameforthesubstitutive(IUPAC)namedsubstance A.4-methyl-2-pentanone B.3-methyl-2-butanone C.2-methyl-3-butanone D.2-methyl-4-pentanone 8. Ingenericreactionsofcarbonylgroups,nucleophilesattack_______________whileelectrophilesattack___________ A.alpha-C;carbonylO B.carbonylO;alphaC C.carbonylO;carbonylCD.carbonylC;carbonylO 9. Whichofthesealdehydes&ketonesislikelytobemostreactivetowardnucleophiles? A.CH3CH2CHO B.CH3COCH3 C.(CH3)2CHCHO D.CH3CH2COCH2CH3 D.NaOH 10. Cyanohydrinsoccurinnatureinallofthefollowingexcept: A.treebarkandleaves B.seedsofstonefruits C.cassava(tapioca) 11. CH3CH2CH2CHOistreatedwithNaBH4inmethanol,thenabitofaqueousacid.Themainorganicproductis A.1-butanol B.butanoicacid C.CH3CH2CH2CH(OCH3)2 D.2-pentanol 12. CH3CH2CH2CHOistreatedwithNH2OH,formingasolidproduct.Thisorganicproductis A.CH3CH2CH2CH2NH2 B.CH3CH2CH2CH2OH C.CH3CH2CH2CH=N-OH D.CH3CH2CH2CH=NH 13. CH3CH2CH2CHOistreatedwithacidicH2Cr2O7.Themainorganicproductis A.CH3CH2CH2CH2OH B.CH3CH2CH2COOH C.CH3CH2CH2CH3 D.CH3CH2CH=CH2 14. Enaminesformwhensuitablealdehydesorketonesreactwith A.anyamines B.primaryamines C.tertiaryamines D.secondaryamines 15. Themainorganicproductofthereactionof3-pentanonewithØ3P=C(CH3)2wouldbe A.trans-4-octeneB.3-ethyl-2-methyl-2-penteneC.cis-4-octeneD.2-ethyl-3-methyl-3-pentene 16. Duetothe–OHofcarboxylicacids,theircarbonylCatomhaswhatreactivitycomparedthatofaldehydes& ketones? A.itisasreactive B.itismorereactive C.itislessreactive 17. TypicalpKavaluesforcommoncarboxylicacidsareabout A.15 B.5 C.1 18. Carbonicacid,H2CO3,isapparentlyaweakeracidthanmightbeexpectedforadicarboxylicacid.Why? A.itisveryunreactive B.CO2doesnotreactmuchwithwaterC.itisinsolubleD.itisagas 19. Whichsequencegivesthebestyieldofbutanoicacidfrom1-butene? A.HBr+peroxide;thenMg+ether;thendryice;H3O+B.Ozone+Zndust;thenaqueousacidicCrO3 C.HBr;thenMg+ether;thendryice;H3O+D.B2H6;thenH2O2/OH–;thenaqueousacidicCrO3 20. Whatreagentorsequenceofreagentswillconvertbutanoicacidintobutanal(CH3CH2CH2CHO) A.H2+Lindlarcatalyst B.B2H6;thenPCCinCH2Cl2C.LiAlH4;H3O+;PCCinCH2Cl2D.NainNH3(l) 21. Theusualreagentusedtoconvertcarboxylicacidstoacylchloridesis A.conc.HCl B.Cl2inCCl4 C.SOCl2 D.somemillipedes D.–3 D.PCl3 CHE312Exam1KEY Page2 22. Whenmalonicacidisheated,itdecomposeseasilybylossof A.H2O B.CH4 C.CO 23. Amongtheacidderivatives,theoneswiththemoststabilized(leastreactive)carbonylgrouparethe A.anhydrides B.amides C.acylhalides D.esters 24. Themostcommonlyavailableandusefulacidderivativesforuseinotherreactionsarethe A.esters B.acylhalides C.amides D.anhydrides 25. Innucleophilicacylsubstitution,thereactionsequenceendswhen A.thecarbonylgroupislost B.atetrahedralintermediateforms C.anucleophileattackscarbonylC D.atetrahedralintermediatedissociates 26. Thebiggestdisadvantageofacidanhydridesasreagentsforuseinsynthesisisthat A.halfthecarboxyliswastedB.theyaretooinertC.theyareveryexpensiveD.theyareunstable 27. WhichoftheacidderivativeswillNOTreactwithaqueousbasetoundergohydrolysis? A.esters B.nitriles C.amides D.allofthemwillreact 28. Tomakecyanobenzene(benzonitrile)fromtoluene,thebestsequencetouseis A.hotKMnO4;NH3,∆;P4O10B.hotKMnO4;NaCNC.NBSinCCl4;Mg+ether;NaCND.NBSinCCl4;NaCN 29. TreatmentofethylbutanoatewithexcessCH3MgBrgiveswhatmainproductafteraqueousacidworkup? A.2-pentanone B.2-methyl-2-pentanol C.2-pentanol D.3-hexanol 30. Tomake4-octanonefromCH3CH2CH2CNyoumustreactitwith______________followedbynormalworkup. A.CH3CH2CH2COCl B.CH3CH2CH2CH2Br C.CH3CH2CH2CH2MgBr D.CH3CH2CH2CH2CH2MgBr D.CO2 Problems(40%;14,12,&14%respectively) I. Thereactionshownbelowwillproducetheethanal’sacetalandwaterasthefinalproducts. DRAWTHESTEPSINTHISMECHANISM.Besuretoincludeallmajorstepsandshowthestructuresofthe mainintermediatesthatareformedalongtheway. O H3C H+ +2CH3CH2OH H H+ O OH OH H H H O O H H OH2 H O Acetalof ethanal H H O O O H H H O –H2O O O CHE312Exam1KEY II. Page3 FischerEsterificationisprobablythemostimportantlabreactionofcarboxylicacids.Forthealcoholand theacidshownbelow,givethemechanismofthisreaction. DRAWTHESTEPSINTHISMECHANISM.Besuretoincludeallmajorstepsandshowthestructuresofthe mainintermediatesthatareformedalongtheway. O H3C OH O H+ +CH3CH2OH H+ OH OH OH OH OH O O H H ethyl ethanoate (ethyl acetate) O H –H2O O theseareminimalsteps;couldalsoincludemorespecifictransfers ofHionsoffandontoOatomsformorecompleteanswers. O O OH2 OH O CHE312Exam1KEY Page4 III. Saponification(basecatalyzedaqueoushydrolysisofanester)isaverycommonlyusedreactionofesters. DRAWTHESTEPSINTHISMECHANISM.Besuretoincludeallmajorstepsandshowthestructuresofthe mainintermediatesthatareformedalongthewayasthefollowingesterissaponified. O H3C O Shouldnoteordrawthelaststepasirreversible–akeyaspectofthisreaction! O O O + O O HO– –O OH OH NOT reversible! O + O– HO