Professional Documents
Culture Documents
Theobjectiveofthislabwastoidentifysixdifferentunknowncompoundsusingfive
differenttestsandreactions.Indoingsoandseeingwhichcompoundsreacteditcouldbe
determinedwhichmoleculeswereeachunknowncompound.Becauseitwaspossibleto
hypothesizehowthedifferentcompoundswouldreactineachtest,itwaspossibletosee
whichunknownsreactedthesamewasasthehypothesizedmoleculeswould.Ifanunknown
reactedthesameineverytestthatamoleculewashypothesizedto,chancesarethatthis
unknownisthatmolecule.
Introduction:
Theobjectiveofthislabwastoidentifysixdifferentunknowncompoundsusingfive
differenttestsandreactions.Thisisimportantbecauseitshowshowwhenasubstanceis
unidentified,puttingitthroughdifferentreactionsandtestscanhelpchemistsdetermine
whattheunknownis.Inthislab,fiveseparatetestsandreactionswereusedinorderto
identifytheunknownsubstances.Thesetestsandreactionsincludedasolubilitytest,a
dihalogenationtestusingbromine,anoxidationreactionwithpotassiumpermanganate,a
Tollenstest,andchromicacidtest.Thesolubilitytestwasatestinwhichthesixdifferent
unknownswereobservedwhetherornottheyweresolubleinwater,anacid(HCl),anda
base(NaHCO3)beforeheatwasaddedandafterheatwasadded.Thedihalogenationtest
wasusedasawaytotestforalkenesandalkynes.Abrominesolutioninbrownandwhen
reactedwithanalkenetheC-Cdoublebondinthealkenebreaksandbondswiththetwo
bromineatoms.Whenthesebondsareformed,thesolutionbecomesclearbecausethereare
nomoreBr-Brbonds.Whentheunknownswereaddedtothesolution,onlythecompounds
thatcontainedaC-Cdoublebondwouldreactwhilenothingwouldhappentotheothers.
Theoxidationreactionwithpotassiumpermanganateisusedtotestforthepresenceof
primaryandsecondaryalcohols,aldehydes,andalkenes.Whenreactedwithprimary
alcohols,analdehydeisformed.Whenpotassiumpermanganateisreactedwithaldehydes,a
carboxylicacidisformed.Whenpotassiumpermanganateisreactedwithasecondary
alcohol,aketoneisformed,andwhenpotassiumpermanganateisreactedwithanalkane,an
alcoholisformed.ATollenstestisusedtotestforthepresenceofanaldehyde.Muchlike
thereactionwithpotassiumpermanganate,chromicacidisusedtotestforprimaryand
secondaryalcoholsaswellasaldehydes.Chromicaciddoesnotreactwithalkenes.When
reactedwithprimaryalcohols,analdehydeisformed.Whenchromicacidisreactedwith
aldehydes,acarboxylicacidisformed.Whenchromicisreactedwithasecondaryalcohol,a
ketoneisformed.Onthenextpageisatableofpredictionsforeachoftheunknown
compoundsbasedontheirfunctionalgroupsandchemicalproperties.
=Noreaction
=Reaction
Table1:PredictionsTable
ResultsandDiscussion:
=Noreaction
=Reaction
Table2:Resultsofdifferentparts
Part1
Thesolubilitytestwasatestinwhichthesixdifferentunknownswereobserved
whetherornottheyweresolubleinwater,anacid(HCl),andabase(NaHCO3)beforeheat
wasaddedandafterheatwasadded.UnknownAwasnotsolubleinanyofthesolutions.
UnknownBwasnotsolubleinanythingaswell.UnknownCwassolubleinwaterafter
beingheatedandacid.UnknownDwassolubleinwaterandacid.UnknownEwassoluble
innothing,andUnknownFwassolubleinwater.
Part2
Thedihalogenationtestwasusedasawaytotestforalkenesandalkynes.Abromine
solutionisbrownandwhenreactedwithanalkenetheC-Cdoublebondinthealkene
breaksandbondswiththetwobromineatoms.Whenthesebondsareformed,thesolution
becomesclearbecausetherearenomoreBr-Brbonds.Whentheunknownswereaddedto
thesolution,onlythecompoundsthatcontainedaC-Cdoublebondwouldreactwhile
nothingwouldhappentotheothers.OnlyUnknownBreactedinthistestsoUnknownB
mustbeanalkeneoranalkyne.
Part3
Theoxidationreactionwithpotassiumpermanganateisusedtotestforthepresence
ofprimaryandsecondaryalcohols,aldehydes,andalkenes.Whenreactedwithprimary
alcohols,analdehydeisformed.Whenpotassiumpermanganateisreactedwithaldehydes,a
carboxylicacidisformed.Whenpotassiumpermanganateisreactedwithasecondary
alcohol,aketoneisformed,andwhenpotassiumpermanganateisreactedwithanalkane,an
alcoholisformed.UnknownsB,E,andF,allreactedinthistestmeaningthatalloftheseare
eitherprimaryorsecondaryalcohols,aldehydes,oralkenes.
Part4
ATollenstestisusedtotestforthepresenceofanaldehyde.Thisisbecausein
aldehydesthereisacarbondoublebondedtoaoxygenandasinglehydrogen.This
compoundcanbefurtheroxidizedbyremovingthehydrogenandreplacingitwithaOH
groupmakingthecompoundacarboxylicacid.Theonlyunknownthatreactedwas
UnknownEsothisunknownmustbeanaldehyde.
Part5
Muchlikethereactionwithpotassiumpermanganate,chromicacidisusedtotestfor
primaryandsecondaryalcoholsaswellasaldehydes.Chromicaciddoesnotreactwith
alkenes.Whenreactedwithprimaryalcohols,analdehydeisformed.Whenchromicacidis
reactedwithaldehydes,acarboxylicacidisformed.Whenchromicisreactedwitha
secondaryalcohol,aketoneisformed.UnknownsB,C,andE,allreactedsothesemustbe
eitherprimaryalcohols,secondaryalcohols,oraldehydes.
Error
Thebiggestsourceoferrorinthislabwasthefactthatwewereunabletocomplete
thesolubilitytests.Becausealotofthesubstanceswerenottestedonwhetherornotthey
weresolubleinbase,thereisnodefinitiveevidencetoconcludewhattheunknownswere.
Conclusion:
Thepurposeofthislabwastoidentifysixdifferentunknownsusingfivedifferent
testsandreactions.Indoingsoandseeingwhichcompoundsreacteditcouldbedetermined
whichmoleculeswereeachunknown.Becauseitwaspossibletohypothesizehowthe
differentcompoundswouldreactineachtest,itwaspossibletoseewhichunknownsreacted
thesamewasasthehypothesizedmoleculeswould.Ifanunknownreactedthesameinevery
testthatamoleculewashypothesizedto,chancesarethatthisunknownisthatmolecule.
Unknowns Molecules
A Cyclohexane
B Cyclohexene
C Butanol
D 2-methyl-2-propanol
E Heptanal
F ButanoicAcid
Table3:MatchingofUnknownsandMoleculesTable
ExperimentalMethods:
Part1:SolubilityTests
1mLofdistilledwater,1mLof1.0MaqueousHCl,and1mLof0.6Maqueous
NaHCO3,wereeachaddedto3separatelabeledtested.1mLofthefirstunknowntoeach
testtubewasaddedintoeachof3labeledtesttubesandshakenvigorouslyforafew
seconds,thentheywereallowedtostand.Afterrecordinginitialobservations,thetubes
wereheldina70oCwaterbathforoneminute,andthenobservedagain.Thesolubilitytests
wererepeatedfortheotherunknowns.
Part2:AdditionofBromine
*INFUMEHOOD
0.1mLofthefirstunknownwasdissolvedin1mLofdichloromethaneinaclean,
drytesttube.A2%solutionofbromineindichloromethanewasaddeddrop-wisewhilethe
testtubewasgentlyagitateduntilthered-brownbrominecolorpersisted.Apositivetest
requiredfiveormoredropsofbrominesolutiontoreachapersistentred-browncolor.The
brominetestwasrepeatedfortheotherunknowns.
Part3:OxidationwithPotassiumPermanganate(BaeyerTest)
Inacleantesttube,2-3dropsofthefirstunknownwasdissolvedin1mLof95%
ethanol.A0.06Msolutionofaqueouspotassiumpermanganatewasaddeddrop-wisewhile
beinggentlyagitated.Apositivetesthadthedisappearanceofthepurplecolortestreagent
andtheformationofabrownprecipitate.Thepermanganatetestwasrepeatedfortheother
unknowns.
Part4:TollensTest
TheTollensreagentwaspreparedimmediatelybeforeitwasplannedonbeingused.
10mLof0.25MAgNO3wasaddedtoalargetesttube.ConcentratedNH4OHwasadded
drop-wise,whilebeinggentlyagitated,untilthebrownsilverhydroxideprecipitate
disappeared,then5mLof0.8MKOHsolutionwasadded.Ifthebrownprecipitate
reformed,moreNH4OHwasadded,drop-wise,untilithaddissolved.Thisproduceda
silverammoniumcomplexandwastheTollenssolutionthatwasusedforthetest.
2mLofthefreshlypreparedTollensreagentwasaddedtoaclean,drytesttube.2-3
dropsofthefirstunknownwasdissolvedintheminimumamountofdiethyletherrequired
togiveaclearsolutioninasecondtesttube.Theunknownsolutionwasaddeddrop-wiseto
thefirsttesttubewhilebeinggentlyagitated,thenstoppedandmixedvigorouslyfor1-5
minutessothattheliquidcomesincontactwiththeentireinnersurfaceofthetube.A
positivetestistheformationofasilvermirrorastheelementalsilveradherestothewallof
theglasstube.TheTollenstestwasrepeatedfortheotherunknowns.
Part5:ChromicAcidTest
*INFUMEHOOD
Thechromicacidsolutionwaspreparedbydissolving1.0gofCrO3in1.0mLof
concentratedsulfuricacidandthencarefullydilutingwith3mLofwater.2-3dropsofthe
firstunknownweredissolvedintheminimumamountofacetonerequiredtogiveaclear
solutioninaclean,drytesttube.Thechromicacidsolutionwasaddeddrop-wisewhilebeing
gentlyagitated.TheorangecoloroftheCr+6ionwasreplacedbythegreencoloroftheCr+3
ionifthesubstratewasoxidizedandthetestreagentwasreduced.Thechromicacidtestwas
repeatedfortheotherunknowns.
References:
D-Band.OrganicChemistry.(2016,May25)[ClassData].Unpublishedrawdata.