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1、AmidationofCarboxylicAcids:preparationofAcetanilideChenXiaolingClass22012364217PurpesesandRequirements(1) Learntheprinciplesandoperationofanilineaceltylation.(2) Consolidatetherecrystallizationmethodandtheprincipleofpurflicationoforganiccompounds.二、Theexperimentalprincinpleanddevices.PrincipleAcetan

2、ilidecanbepreparedfromanilineinseveralways,usingacetylchloride,aceticanhydrideorglacialaceticacidasstartingmaterials.Acetylchloridereactsveryvigorously.Aceticanhydrideispreferredforalaboratorysynthesisbecauseitsrateofhydrolysisislowenoughtoallowtheacetylationofaminetobecarriedoutinaqueoussolution.It

3、givesaproductofhighpurityandingoodyield.Theprocedurewithglacialisofcommercialinterestsinceitiseconomical,butitrequireslongheating.Inthepresentexperiment,wecanuseeitherofthefollowingmethodstopreparetheacetanilide.Themainreaction:DevicesCH3COOHNHCOCH3-卜H2OThermometerElbownmuloc FractiontingMeasuring c

4、ylinderRound bottom flaskApparatus for preparation of acetanilide三、MaterialsandPhysicalconstantsCompoundfwRelativedenistyMp/CBp/CRefractiveindex(n20D)Solubility/inthewaterAcetanilide135.171.2190113-1143050.53(6C)Aniline93.131.022-6.1184.41.58633.6(18C)Glacialaceticacid60.051.049216.6117.61.3716四、Pro

5、cedure5mL50mLround-bottomThe acetanilideforms,WAHeat the mixtureto refluxLet the mixtureinto a beaker withCollect theice-cold water,andrecrystallize fromfiltrationwaterproduct by suctionOOH+0.1 即 in theAniline+7.5mL CH?C100mL of theWash it with theKeep the temperature of the distilling vapor being a

6、bout 105 CAfter 1h,thereaction hasfinishedRecord the massthe percentage yieldand melting range of the acetanilideobtained ,calculate五、TheresultanddataanalysisTheresult0.055molThetheoryofprodurction:m(Acetanilide)=0.055x135.17=7.4gTheactualyield:1.8gTheproductivityoftheAcetanilide:0=1.8+7.4x100%=24.3

7、%Analysis1、Getthe3.2gofacetanilideandyieldisabout63%2、Inthisreaction,weuseexcessofaceticacid.Ononehand,forlowcostandeasytocontrol,ontheotherhand,theglacialaceticacidiseasytodissolveinthewater.Sowecanseparateitfromproduct.3、Zincpowderidaddedtopreventtheanilinefrombeingoxidizedduringreaction.Donotaddt

8、oomuch,otherwisethewater-insolublezinchydroxidewouldappearintheprocedureofwork-up.4、Inordertopreventtheanilinefrombeingoxidizedduringthereaction,zincpowdershouldbeadded.5、Ifthesolutionhascolor,thanaddasmallamountofactivatedcharcoal,swirlthemixtureandallowittoboilgentlyforafewminutes,andfilteroutthecarbon.6、Theproductinspection,met

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