CHM 2202 Organic Chemistry Lab II
Spring 2011 Department of Chemistry Villanova University
Part 1. Preparation of 2,4­Dintrophenol !"#$%&'()*%+,-%.+/0%12%3)445%64'"7%'28%9':)"%
6'");%<%=1>41'2#?%&'()*%/@,./+A%
:ote; <== materia=s are to>ic? irritating andAor corrosiBeC Dear g=oBes and carry oEt a== reactions in the hoodC Dispose of a== Faste in the Faste container in the hoodC CLEAN UP IMMEDIATELY ANY SPILLED MATERIALS!! 1C Go a 2H mI roEndJKottom f=asL? add the fo==oFing; aC 0.2 g of 2?MJdinitroch=oroKenNene KC 4.0 mL of 2 M aOEeoEs potassiEm hydro>ide PQOHR so=Etion cC 0.85 mL of methano= 2C Darm the resE=ting mi>tEre to S H0 ! T0U C on a steam Kath Fith sFir=ing Enti= the so=id 2?MJdinitroch=oroKenNene me=ts PNOTE: the solid does not dissolve, but forms a blob of oil on the bottom of the flaskRC VC OKtain 1 mL of VW aOEeoEs hydrogen pero>ide PH2O2R in a gradEated cy=inderC MC <dd ~ P (0.25 mLR of the hydrogen pero>ide so=Etion to the Farm Pthe temperatEre of "#$%&'()*+)%,-."$.")%)#-/'0%1$%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 hydrogen pero>ide? restopper and shaLe again for another seBera= minEtesC ^C Dhen so=ids Kegin to appear in the darL so=Etion? remoBe 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=Bed? continEe Fith the ne>t stepC Page 1 of 3
CHM 2202 Organic Chemistry Lab II
Spring 2011 Department of Chemistry Villanova University
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 in the ar=enmeyer f=asL so that the mi>tEre in the f=asL is a =ight 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 diBided 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 me=ting point range of yoEr prodEctC 20C <na=yNe and interpret the infrared spectra of starting materia= 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 2,4­Dinitrohalobenzenes with Ammonia and Hydrazine Page 2 of 3
CHM 2202 Organic Chemistry Lab II
Spring 2011 Department of Chemistry Villanova University
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 comp=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?MJ
dinitrof=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 minEtesC 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 minEte 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 prodEct 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 Dhich compoEnd J 2?MJdinitroch=oroKenNene or 2?MJdinitrof=EoroKenNene ! FoE=d yoE e>pect to react faster Fith nEc=eophi=esc Dere yoEr e>pectations Korne oEt Ky yoEr e>perimenta= oKserBationsc KC HoF do yoE e>p=ain the differences in the reaction rates of ammonia BsC hydraNine Fith each of the ha=oKenNenesc cC Do the yie=ds of the compoEnds yoE oKtained corre=ate in any Fay Fith the e>pected rates of reaction of the ammonia and hydraNine Fith the ha=oKenNenesc ^C de sEre to p=ace a== fi=trates and other residEes from this e>periment in the Faste container in the commEnity hoodC GMdare P1A[A2011R Page 3 of 3