glucose pentaacetate worksheet：葡萄糖五乙酸酯表

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1、OrganicChemistryLab,CHEM272WCUChemistryDepartmentSynthesisIVWorksheetSugars:TheGlucosePentacetatesName:1.(10pts.)Whataretheyieldsfortheglucosepentacetateisomers?Whichisomerdidyousynthesize?Showcalculationsforthetheoreticalandpercent%yieldforyourisomer.Theor.YieldActual

2、YieldPercentYieldWhoSynthesizedaisomer:bisomer:TheoreticalandPercentYieldCalculations:2.(20pts.)Attach1HNMRspectraofboththeaandbisomers.(Makeacopyofpartner’sspectrum.)Comparethetwospectra,focusingonthechemicalshiftandcouplingconstantsoftheanomericprotonsatC-1.Discusswh

3、ythespectraaredifferent.(Seepage380ofthelabtext.)Drawthestructureofeachisomerinitschairconformation.3.(5pts.)Provideadetailedmechanismfortheformationofthebisomerfromglucoseandaceticanhydride.Usearrowstoshowthemovementofelectrons.OrganicChemistryLab,CHEM272WCUChemistryD

4、epartment1.(10pts.)Whatweretheexperimentallydeterminedmeltingpointsforbothisomers?Howdothesevaluescomparetheliteraturevaluesfortheglucosepentacetates?Whatcanyouconcludeaboutthepurityofeachisomerfromthemeltingpointdata?ActualLiteratureMeltingpointofaisomerMeltingpointof

5、bisomerPurity:2.(5pts)Whatstructuralfactorsfreezeeachoftheglucosepentacetatesinasinglechairconformation?(Inotherwords,whydoesthechairofthiscompoundnotflip?)3.(5pts)Glucoseisthemostcommonmonosaccharide(simplesugar)foundinnature.Whyisglucosefavoredoverothersugars?(Thinka

6、boutstructureandstabilityofglucoseandothersugars.)OrganicChemistryLab,CHEM272WCUChemistryDepartment1.(5pts)Whatcyclicstructuresotherthanthe6-memberedringglucopyranosemightD-(+)-glucoseform?2.(5pts)Brieflydefineordescribethefollowingtermsrelatedtoglucose.(Seechapter25of

7、theChem242lecturetext.)CarbohydrateSimpleSugarHexoseAldoseFuranose3.(10pts)Fillinstructuresornamesforthefollowingcompounds,followingthepatternforglucose.(Seepage950ofthelecturetext.)Besuretocountcarbons!OrganicChemistryLab,CHEM272WCUChemistryDepartmentBrieflyexplainthe

8、differencebetweend-glucoseandd-galactose.1.(10pts)Onasinglegraph,sketchpotentialenergy-diagramsfortheconversionofgluc