CHM$2202$ Spring$2011$ Department$of$Chemistry$Organic$Chemistry Lab II Villanova University Page 1 of 3 Part%1.%%Preparation%of %2,41Dintrophenol%!"#$%&'()*%+,-%.+/0%12%3)445%64'"7%'28%9':)"%6'");%<%=1>41'2#?%&'()*%/@,./+A% :ote;$$<==$materia=s$are$to>ic?$irritating$andAor$corrosiBeC$$Dear$g=oBes$and$carry$oEt$a==$reactions$in$the$hoodC$$Dispose$of$a==$Faste$in$the$Faste$container$in$the$hoodC$$CLEAN%UP%IMMEDIATELY%ANY%SPILLED%MATERIALS!!%$1C Go$a$2H$mI$roEndJKottom$f=asL?$add$the$fo==oFing;$aC 0.2%g$of$2?MJdinitroch=oroKenNene$KC 4.0%mL$of$2$M$aOEeoEs$potassiEm$hydro>ide$PQOHR$so=Etion$cC 0.85%mL$of$methano=$2C Darm$the$resE=ting$mi>tEre$to$S$H0$!$T0U$C$on$a$steam$Kath$Fith$sFir=ing$Enti=$the$so=i d$2?MJdinitroch=oroKenNene$me=ts$$PNOTE:%the%solid%does%not%dissolve,%but%forms%a%blob%of%oil%on%the%bottom%of%the%flaskRC$VC OKtain$1%mL$of$VW$aOEeoEs$hydrogen$pero>ide$PH2O2R$in$a$gradEated$cy=inderC$MC <dd$~%P$(0.25%mLR$of$the$hydrogen$pero>ide$so=Etion$to$the$Farm$Pthe$temperatEre$of$"#$%&'()*+)%,-."$.")%)#-/'0%1$%23%!$T0UCX$the$reaction$Fi==$not$Ke$sEccessfE=$if$yoEr$f=asL$is$not$Farm$enoEghR$roEnd$Kottom$f=asL$containing$the$me=ted$so=idC$HC Ymmediate=y$stopper$the$f=asL$Fith$a$groEnd$g=ass$stopperX$ho=ding$the$stopper$in$p=ace$Fith$yoEr$hand?$shaLe$the$Farm$f=asL$BigoroEs=y$for$V$to$M$minEtesC$TC CarefE==y$ remoBe$the$ stopper$Keing$ carefE=$ not$to$ contact$ yoEr$ sLin$ Fith$ the$ so=Etion$remaining$on$the$stopperC$$ZoE$may$Fant$to$Ese$a$paper$toFe=$to$hand=e$the$stopperC$[C \sing$a$steam $Kath?$reFarm$the$f=asL$and$its$contents$to$S$T0UCC$]C Go$ the$ Farmed$ PST0UCR$ contents$ in$ the$ f=asL?$ immediate=y$ add$ another$ P$ P0.25% mLR$portion$ of$ the$ aOEeoEs$ hy drogen$ pero>ide?$ rest opper$ and$ shaLe$ again$ for$ another$seBera=$minEtesC$^C Dhen$ so=ids$ Kegin$to$ appear$ in$ the$darL$so=Etion?$ rem oBe$ the$ stopper$and$ Farm$the$f=asL$on$the$steam$Kath$Enti=$the$so=ids$redisso=BeX$if$so=ids$do$not$appear?$_Est$reFarm$the$f=asL$to$T0UC$and$continEe$to$ne>t$stepC $10C <dd$a==$of$the$remaining$hydrogen$pero>ide$P~0.50%mLR$and$sFir=$the$f=asL$Fhi=e$heating$on$the$steam$Kath$Enti=$no$more$oi=y$drop=ets$can$Ke$seen$on$the$Kottom$of$the$f=asL$PSH$!$10$minEtes$heating$at$T0$ ! $ THUC$shoE=d$Ke$sEfficientRC$$Gry$to$get$most$of$the$oi=$to$disso=BeC$$Yf?$after$10$minEtes$of$heating?$the$oi=$has$sti==$not$disso=B ed?$continEe$Fith$the$ne>t$stepC$$CHM$2202$ Spring$2011$ Department$of$Chemistry$Organic$Chemistry Lab II Villanova University Page 2 of 3 $$11C `oEr$the$resE=ting$so=Etion$into$a$2H$mI$ar=enmeyer$f=asLX$rinse$the$reaction$f=asL$Fith$a$few%tenths%mL$of$Fater$Pp=ace$the$rinse$in$the$ar=enmeyerRC$12C Coo=$the$ar=enmeyer$f=asL$in$an$ice$Kath$Fith$stirring$Pg=ass$rodRC$1VC Yn$a$separate$sma==$container$add$ 1%mL$of$concentrated$hydroch=oric$acid$PHC=R$to$~%1%mL$of$crEshed$iceC$1MC <dd$this$co=d$di=Eted$acid$dropFise$ to$the$coo=ed$stirred$so=Etion$i n$the$ar=enmeyer$f=asL$so$that$the$mi>tEre$in$the$f= asL$i s$a$=i ght$ye==oF$co=orC$1HC \sing$ a$ g=ass$ rod?$stir$ the$ resE=ting$ mi>tEre$ for$ seBera=$ minEtesX$Ke$ sEre$to$KreaL$ any$so=id$chEnLs$into$a$fine=y$diB ided$so=id$Ky$rEKKing$the$so=id$against$the$f=asL$Fa==$Esing$yoEr$g=ass$stirring$rodC$1TC Co==ect$the$resE=ting$so=id$on$a$sma==$Hirsch$fEnne=$Esing$BacEEm$fi=trationC$1[C IeaBe$the$BacEEm$on$and$carefE==y$Fash$the$co==ected$so=ids$Fith$~0.5%mL$of$di=Ete$PHWR$HC=$and$then$Fith$several%mLs$of$FaterC$$$1]C <==oF$ the$ so=ids$ to$air$ dry$ on$ the$ Hirsch$fEnne=$ Ky$ continEing$ to$sEcL$ air$ throEgh$ the$fEnne=$for$10$!$1H$minEtesC$1^C Deigh$the$dried$so=id?$ca=cE=ate$the$W$yie=d$and$determine$the$m e=ting$ point$ range$of$yoEr$prodEctC$$$20C <na=yNe$ and$ interpret$the$ infrared $ spectra$ of$ starting$ m ateria=$ and$ prodEct$ that$ Fere$proBided$ as$ handoEtsC$ $ Ghe$ appearance$ or$ disappearance$ of$ Fhich$ Ley$ Yb$ aKsorption$Kand$indicates$that$the$starting$materia=$has$Keen$conBerted$to$prodEctc$$$$ Part%2.%%Reaction%of%2,41Dinitrohalobenz enes%with%Ammonia%a nd%Hydrazine%%%CHM$2202$ Spring$2011$ Department$of$Chemistry$Organic$Chemistry Lab II Villanova University Page 3 of 3 1C Yn$a$sma==$test$tEKe$P:oC$1R?$add$0.06%g$of$2?MJdinitrochloroKenNene$and$1%mL$of$ethano=C$$SFir=$the$test$tEKe$to$disso=Be$a==$of$the$crysta=s$of$the$2?MJdinitroch=oroKenNeneX$s=ight$Farming$may$Ke$necessary$to$disso=Be$the$crysta=s$com p=ete=yC$$$2C Once$disso= Bed?$Ese$a$disposaK=e$pipette$to$transfer$ha=f$of$the$so=Etion$to$another$test$sma==$test$tEKe$P:oC$2RC$$$VC Go$another$test$tEKe$P:oC$3R$asL$a$Geaching$<ssistant$to$Ese$a$syringe$to$add$0.04%mL$of$2?MJdinitrofluoroKenNene$ P:OGa;$ $ this$ materia=$ is$ a$ cancer$ sEspect$ agent$ and$ a$ =oF$me=ting$so=id$J$mp$2HJ2[U$ C$J$and$may$haBe$to$ Ke$ Farmed$in$its$container$to$oKtain$a$=iOEid$Fhich$can$Ke$FithdraFn$into$a$syringeR$and$1%mL$of$ethano=C$ $SFir=$to$disso=Be$the$oi=y$ =iOEid$ comp=ete=yX$ e>amine$ the$ test$ tEKe$ c=ose=y$ to$ maLe$ sEre$ a==$ of$ the$ oi=y$ 2?MJdinitrof=EoroKenNene$has$disso=BedC$$$MC Once$disso=Bed?$transfer$ha=f$of$this$so=Etion$to$another$test$tEKe$P:oC$4RC$HC Go$each$of$test$tEKes$:oC$1$and$3?$add$0.04%mL$of$concentrated$ammoniEm$hydro>ide$PcaEtion;$Kad$odor?$can$caEse$eyes$to$tearR?$sFir=$to$mi>$comp=ete=y?$note$the$e>act$time$of$addition$and$ record$any$changes$ that$occEr$in$the$tEKes$oBer$the$ne>t$V0$minEtesC$$Yn$particE=ar?$note$the$time$e=apsed$for$the$formation$of$a$precipitate$Pif$anyR$and$any$co=or$changes$that$occErC$TC IiLeFise?$to$ each$ of$ test$ tEKes$ :oC2$ and$ 4?$haBe$ a$ Geaching$ <ssistant$add$ 0.02% mL$ of$]0W$hydraNine$ hydrate$PcaEtion;$sEspected$carcinogenR?$ note$the$time$of$addition$and$record$any$changes$that$occEr$in$the$tEKes$oBer$the$ne>t$V0$mi nEtesC$Yn$particE=ar?$note$the$time$e=apsed$for$the$formation$of$a$precipitate$Pif$anyR$and$any$co=or$changes$that$occErC$[C <fter$the$V0$mi nEte$time$periods$ haBe$e>pired?$Ese$a$Hirsch$fEnne=$to$iso=ate$and$ co==ect$any$crysta==ine$prodEcts$Fhich$formedC$\se$ethano=$to$Fash$the$prodE ct$oEt$of$the$test$tEKes$and$then$air$dry$ each$of$the$co==ected$so=ids$ on$the$Hirsch$fEnne=$Ky$sEcLing$air$throEgh$the$crysta=s$for$seBera=$minEtes$Enti=$the$so=ids$are$dry$and$free$f=oFingC$$Deigh$the$so=ids$and$ca=cE=ate$the$W$ yie=ds$of$the$prodEcts?$assEming$the$dinitroha=oKenNenes$are$the$=imiting$reagentsC$]C Compare$the$resE=ts$of$this$e>periment$and$e>p=ain$the$reactiBity$that$Fas$oKserBedC$$de$sEre$to$ansFer$the$fo==oFing$OEestions;$aC