PS4 Key - Chemistry262Iha ANSWERKEY ProblemSet4 CHAPTER...

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Unformatted text preview: Chemistry262 Iha ANSWERKEY ProblemSet4 CHAPTER 18 ALDEHYDES AND KETONES QUESTION 1 MECHANISMS Acid Catalyzed Addition A)Drawthemechanismfortheacidcatalyzedformationofthedithianeshownbelow   B)Drawthemechanismfortheacidcatalyzedformationoftheacetalshownbelow     C)Acetalformation(aswellasdithianeformation)isanequilibriumreaction.Assuch,thereactioncanbereversed.Showhowthe acetalgroupcanberemovedandtheketonecanbereformedthroughareactionwithwater.      Chemistry262 Iha ANSWERKEY ProblemSet4  QUESTION 1 MECHANISMS Acid Catalyzed Addition cont. D)TheWolff Kishnerreductionisamethodfordeoxygenatingacarbonyltoproduceanalkane.ThefirststepintheWolf Kisher Reductionistheformationofahydrazone(atypeofimmine)throughthereactionofaketoneoraldehydewithhydrazine.Drawthe mechanismforthisstepbaseduponthereactionbelow.    Thesecondstepinvolvesreactionofthehydrazonewithhydroxidetoyieldthealkaneandnitrogengas.Drawthemechanismforthis stepintheWolff KishnerReductionbaseduponthereactionbelow.    E)Drawthemechanismfortheacid catalyzedgenerationoftheenolshownbelow      Chemistry262 Iha ANSWERKEY ProblemSet4 QUESTION 2: Practice Problem Thefollowingdithianecanbeformedbythereactionofformaldehydewithadithiol.Ifyouwouldlikemorepractice,drawthe mechanismforthegenerationofthedithianeshownbelow.    Thisdithianecanundergoaseriesofusefulreactions/transformationstoyieldaldehydesandketones.Fillintheboxesbel owwiththe productsresultingfromeachstep.    QUESTION 3: Practice ProblemDithianescanmakeexcellentnucleophiles(asshowninquestion3).Goodnucleophilesarealso knownforreactingwithketonesandandaldehydes.Fillintheboxesbelowwiththeproductsresultingfromeachstep.   Chemistry262 Iha ANSWERKEY ProblemSet4  QUESTION 4: Mechanisms A)Drawthemechanismfortheoxidationofbenzaldehydeinthepresenceofwater,acidandCrO3(i.e.conditionsfortheJones Oxidation)     B)DrawthemechanismandresultingproductfortheWittigreactionshownbellow       ...
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