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Abstract:

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

Part# Cyclohexan Cyclohexen Butanol 2-methyl- Heptanal Butanoic


e e 2-propano acid
l

1a: Normal: Normal: Normal: Normal: Normal: Normal:


Soluble
inwater Hot: Hot: Hot:
Hot: Hot: Hot:

1b: Normal: Normal: Normal: Normal: Normal: Normal:


Soluble
inacid Hot: Hot:

Hot: Hot: Hot: Hot:

1c: Normal: Normal: Normal: Normal: Normal: Normal:


solublein
base Hot: Hot: Hot: Hot: Hot:
Hot:

Table1:PredictionsTable

ResultsandDiscussion:

=Noreaction

=Reaction

Part# Unknown Unknown Unknown Unknown Unknown Unknown


A B C D E F

1a: Normal: Normal: Normal: Normal: Normal: Normal:


Solublein
water Hot: Hot: Hot:

Hot: Hot: Hot:

1b: Normal: Normal: Normal: Normal: Normal: Normal:


Solublein
acid Hot: Hot: Hot:
Hot: Hot: Hot:

1c:soluble Normal: Normal: Normal: Normal: Normal: Normal:


inbase
Hot: Hot: Hot: Hot: Hot: Hot:

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.