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CHEMICALTESTSFORIDENTIFYINGORGANICFUNCTIONAL

GROUPS
DocBrown'sChemistryQualitativeMethodsofAnalysisRevisionNotes

DocBrown'sChemistryRevisingAdvancedOrganicChemistry

ChemicalidentificationTESTSPart2Qualitativeteststoidentifyorganicmolecule
functionalgroups

FunctionalgrouptestsforalkenesRCH=CHR,hydroxygroupfunctionalgroupprimary,
secondary&tertiaryalcoholsROH,phenols,carboxylicgroupRCOOH,acyl/acidamide
groupRCONH2,acyl/acidchloridegroupRCOCl,aliphaticaminegroupRNH2,
aryl/aromaticamine,aldehydefunctionalgroupRCHO,ketonefunctionalgroupRCOR,
halogenoalkanes/haloalkanes(chloroalkane,bromoalkane,iodoalkane)RCl,RBr,RI,
estersRCOORandtheiodoformtestCHI3

also=Part11QualitativeAnalysisTestforandidentifyorganicfunctionalgroupsnotes

ChemicalTestsIndex

Part1Introduction

Part2Qualitativeteststoidentifyorganicmoleculefunctionalgroupsofhomologousseries(thispage)

Part3Metalcations(positiveions),metalcarbonates,ammoniumionandhydrogenions(acids)

Part4Gases,waterandnonmetallicelements

Part5Anions(negativeions)includinghydroxide(alkalis)

APPENDIX1.IDENTIFYINGELEMENTSfromLINESPECTRA(nonchemicaltestmethod)

someassociatedrevisinglinks

GCSE/IGCSERevisionQUIZonchemicaltestsforidentifyingions,gasesandcompounds

ALevelQuantitativeanalysis:acidbase,silvernitratechloride,EDTAtitrations

ALevelQuantitativeanalysis:Redoxtitrations

FulllistofKEYWORDSforinorganic/organicidentificationmethodsinalphabeticalordere.g.test/reagentfor:*acid==>H+*
acid/acylchlorideRCOCl*alcoholsgeneralROH/primRCH2OH/secR2CHOH/tertR3COH)*aldehydeRCHO*primaliphaticamine
RNH2*aliphatic/aromaticcarboxylicacids*alkali==>OH*alkane/alkene>C=C</alkyneC C(saturatedversusunsaturated)*
aluminium/aluminumionAl3+*amideRCONH2*primaliphaticaminesRNH2*ammoniagasNH3*ammoniumionNH4+*prim
aromaticamineC6H5NH2etc.*bariumionBa2+*Benedict'ssolution*Brady'sreagent*bromideionBr*bromineBr2*caesiumion
Cs+*calciumionCa2+byflameorhydroxideppt.*carbonateCO32/hydrogencarbonateHCO3withacidoreffectofheatingmetal
carbonatee.g.MCO3*carbondioxidegasCO2*carboxylicacidRCOOH*carboxylicacid(aliphatic)saltse.g.RCOONa+*chlorideion
Cl*chlorinegasCl2*Chomate(VI)ionCrO42*copper(II)ionCu2+byflameorhydroxideppt.*24DNPH(foraldehydes/ketonestest)*
estersRCOOR*Fehling'stest/solution*flametestformetalions*fluorideionF*haloalkanes/halogenoalkanesRX*hydrogengas
H2*hydrogensulphideH2S*hydrogenion,acidsH+*hydrogenbromidegas/hydrobromicacidHBr*hydrogenchloridegas/hydrochloric
acidHCl*hydrogeniodidegas/hydriodicacidHI*hydroxideion,alkaliOH*hydroxy/alcohol/phenol(organic)*iodideionI*iodineI2*
iodoformtestformationofCHI3*iron(II)ionFe2+*iron(III)ionFe3+*ketoneR2C=O*lead(II)ionPb2+*lithiumionLi+*limewater
Ca(OH)2(aq)*magnesiumionMg2+*metalcarbonatesheatinge.g.MCO3*metalionsviahydroxideprecipitate*nitrateornitrate(V)
NO3*nitriteornitrate(III)NO2*nitrogendioxideornitrogen(IV)oxideNO2*oxygengasO2*phenolsC6H5OHetc.*potassiumionK+
*rubidiumionRb+*reducingsugars*saturated/unsaturated*silvernitrateAgNO3(seechloride,bromide,iodidetests)*sugars
(reducing)*sodiumionNa+*strontiumSr+*'sulphate/sulfate'orsulphate(VI)SO42*sulphideS2*'sulphite/sulfite'orsulphate(IV)
SO32*sulphurdioxidegasSO2*Tollen'sReagent*unsaturated/saturated*waterH2O*zincionZn2+*

Usethealphabeticaltestlistaboveforidentifyinganions,cations,gases,moleculesetc.tofindwhatyourequire!foryourKS3KS4
ScienceGCSEIGCSEChemistryandGCEASA2IBUSgrades912K12advancedsubsidiarychemistrycourseetc.andhelpyou
toidentifyunknowninorganicandorganiccompoundsmoleculesforqualitativeanalysis.

EMAILquery?comment?testmissing?*GasPreparations*Hazardwarningsigns/symbolsexamplesoflabelling

2.QualitativeORGANICfunctionalgrouptestsinvarioushomologousseries

CHEMICALTEST TESTMETHOD OBSERVATIONS TESTCHEMISTRYandcomments


FOR

ALKENEor Bubblegasthrough,or Theorange/brown R2C=CR2+Br2==>BrR2CCR2Br


alkynechemical addliquidto,asolution brominerapidly
testi.e.any ofbromineinhexaneor decolourises,asa RC CR+2Br2==>Br2RCCRBr2
nonaromatic water. saturated
unsaturated colourless R=H,alkyloraryl
hydrocarbonwitha organicbromo
doubleortriple compoundis Saturatedalkanesgivenofastreactionwithbromine.
carboncarbon formed.
bond.

Hydroxygroup (i)Mixitwithafewdrops (i)Litmusturnsred (i)ROH+CH3COCl==>CH3COOR+HCl


ROHchemical ofethanoylchloride,test andawhite
testinalcohols fumeswithlitmusand precipitatewith Anesterandhydrogenchlorideareformed
andphenols(in'dry' silvernitrate(*note silvernitrate(aq)
conditions*) ethanoylchloridereacts (droponendof (ii)ROH+PCl5==>RCl+POCl3+HCl
withwater,phenolsand glassrod),ifthe
aminestoo!). mixtureispoured achlorocompoundandhydrogenchlorideareformed.
intowateryoumay
Thefirst3tests(i) (ii)Mixitwithalittle detecta'pleasant' (i)and(ii)Ag+(aq)+Cl(aq)==>AgCl(s)fromthehydrogen
(iii)givenonthe phosphorus(V)chloride esterodour,can chloridefumesdissolvedinwater.
rightarequite andtestasabove. testforHClbut
generalformost waterandamines (iii)CH3COOH+ROH==>CH3COOR+H2O
alcohols. (iii)Warmwithalittle produceittoo!
ethanoicacidandafew
dropsofconc.sulphuric (ii)asfor(1)butno
acid.Pourintowater. estersmell!

(iii)Youshouldget
a'pleasant'
characteristicsmell
ofanester.

Primaryalcohol (i)Lucastestshakea (i)Solutionremains (i)Notusuallyreactiveenoughtoformaprimary


chemicaltest fewdropswithcoldzinc clear. halogenoalkane
chlorideinconc.HCl(aq)
RCH2OH,R=H, (ii)Ifproduct (ii)RCH2OH+[O]=>RCHO+H2Oorthefullworks!
alkyloraryl(NOTa (ii)Distilwithpotassium distilledoff
phenol). dichromate(VI)andmod. immediatelyan 3RCH2OH+Cr2O72+8H+==>
conc.H2SO4(aq) aldehydeodour
(ii)isnotagoodtest canbedetected
andthesolution 2Cr3++3RCHO+7H2O
onitsown,sinceso
manyotherreadily colourchanges
reducibleorganic fromorangeto Theorangedichromate(VI)ionisreducedtothegreen
compoundswillgive green. chromium(III)ion.Iftheorganicproductiscollectedyou
couldtestforanaldehyde.
thesamereaction,
thoughfollowingitup
bytestingforan
aldehydegivesit
muchmorevalidity.

Secondaryalcohol (i)Lucastest. (i)Solutionmay (i)Maybereactiveenoughtoslowlyformaninsoluble


chemicaltest cloudveryslowly secondaryhalogenoalkane:R2CHOH+HCl=>R2CHCl+
(ii)Distilwith orremainsclear H2O
R2CHOH,R=alkyl K2Cr2O7/H2SO4(aq) (hitandmiss)
oraryl. (ii)R2CHOH+[O]=>RCOR+H2Oorthefullworks!
(ii)Ifproduct
(ii)isnotagoodtest distilledoff
onitsown,sinceso immediatelya 3R2CHOH+Cr2O72+8H+==>
manyotherreducible ketoneodourcan
organiccompounds bedetectedand 2Cr3++3RCOR+7H2O
willgivethesame thesolutioncolour
reaction,though changesfrom Theorangedichromate(VI)ionisreducedtothegreen
followingitupby orangetogreen. chromium(III)ion.Iftheorganicproductiscollectedyou
testingforaketone couldtestforanaldehyde.
givesitmuchmore
validity.

Tertiaryalcohol (i)Lucastest. (i)Goescloudy (i)Reactiveenoughtoimmediatelyformaninsoluble


chemicaltest veryquickly. tertiaryhalogenoalkaneR3COH+HCl=>R3CCl+H2O
(ii)Distilwith
R3COH,R=alkylor K2Cr2O7/H2SO4(aq) (ii)Noaldehydeor (iii)Stabletomodestoxidation.
aryl. ketonereadily
formed

Phenols(OH Addafewdropsof Usuallygivesa (seealsotestforprimaryaromaticaminesuseitin


groupis iron(III)chloridesolution purplecolour. reversestartingwithaknownprimaryaromaticamine!)
attached toalittleofthephenolin
directlytoaromatic water.
ring)chemicaltest.
ROH,whereRis
aryle.g.C6H5OH

Carboxylicacids Mixthecarboxylicacid fizzing,colourless RCOOH+NaHCO3==>RCOONa+H2O+CO2


chemicaltest withwaterandadda gasgiveswhite
littlesodium precipitatewith (seealsosaltsofaliphaticcarboxylicacidsbelow)
RCOOH hydrogencarbonatesolid limewater
orsolution.

Saltsofaliphatic Addalittledilute Thesolidor Thestrongeracid,HCl/H2SO4displacestheweaker


carboxylicacidse.g. hydrochloric/sulfuricacid solutionshould aliphaticcarboxylicacidwhichhavestrongpungent
RCOONa+or toasuspectedsaltofan havenostrong characteristicodourse.g.
aliphaticcarboxylicacid. odour,butafter
(RCOO)2Mgetc.
addingthemineral ethanoicacidfromanethanoatesalt(smellofaceticacid,
acidyoushouldget vinegar)andbutanoatesreleasebutanoicacid(butyricacid,
apungentodourof rancidodour).
theoriginal
aliphaticacid.Ifits
thesaltofan
aromaticcarboxylic
acid,yougetlittle
odourandmaybea
whitecrystalline
precipitate.

AcidorAcyl (i)Addafewdropsto (i)Litmusturnsred (i)RCOCl+H2O==>RCOOH+HCl


Chloride water,testwithlitmus andawhite
chemicaltest andsilvernitrate precipitatewith TheacidchlorideishydrolysedtoformHClacid(chloride
solution. silvernitrate. ions)andtheoriginalcarboxylicacid.
RCOCl
(ii)Addtoalittleethanol (ii)Asaboveand (ii)CH3CH2OH+RCOCl==>RCOOCH2CH3+HCl
Fumesinairforming andpourthemixtureinto youmaydetecta
HCl(g) water. 'pleasant'ester anethylesterandhydrogenchlorideareformed
odour.

AcidAmide Boilthesuspectedamide ammoniaevolved RCONH2+NaOH==>RCOONa+NH3


chemicaltest withdilutesodium onboiling(noheat
hydroxidesolution,see requiredtoform
RCONH2 ininorganicfor ammonia,ifitwas
ammoniatests. anammoniumsalt)
Aliphaticamines (i)Lowermembers (i)Afishyodour, (i)Unlessitsaliquidorsolid,onlythemorefishyodour
(primary,whereR= solubleinwaterbuta litmusturnsblue, distinguishesitfromammonia.
alkyl)chemicaltest veryfishysmell!testwith whitecloudswith
RNH2 redlitmusandconc. HCl. (ii)Thereactionise.g.
HCl(aq)fumes.
e.g.CH3CH2CH2 (ii)Theaboveis RNH3++OH==>RNH2+H2O
NH2 (ii)Ifasuspectedsaltof notobserveduntil
anamine,thenadd afteraddingthe
sodiumhydroxide alkali.
solutiontofreethe
amine.

Aromatic (i)Dissolvetheprimary (i)Itshouldbea (i)Ifaprimaryaromaticamine,a'stable'diazoniumsaltis


amines aromaticamineindilute clearsolutionwith formed.Diazoniumsaltsfromaliphaticaminesdecompose
chemicaltest hydrochloricacidat5oC few,ifany,brown rapidlyevolvingcolourlessnitrogen.
(whereR=arylwith andmixwithsodium fumes.
theamineoramino nitritesolution. (ii)Anazodyestuffmoleculeisformedinacouplingreaction
groupdirectly (ii)Acoloured e.g.
attachedtoan (ii)Addaphenol precipitate[red
aromaticring)RNH2 dissolvedindilute brownyellow C6H5N=NC6H4OH
sodiumhydroxide. etc.]
e.g.C6H5NH2

Aldehydeschemical (a)Addafewdropsof (a)Ayellow Thealdehydeorketone2,4dinitrophenylhydrazoneis


test(RCHO,R=H, thesuspectedcarbonyl orangeprecipitate formed
alkyloraryl)to compoundtoBrady's formswithboth
distinguishfrom reagent(2,4 typesofcarbonyl R2C=O+(NO2)2C6H3NHNH2==>
ketones(R2C=O,R= dinitrophenylhydrazine compound.
alkyloraryl)and solution) (NO2)2C6H3NHN=CR2+H2O
alsoreducing
sugars. (R=H,alkyloraryl)

Note Thistellsyouitsanaldehydeorketone,butcan't
distinguishthem,readonbelow!
(1)Test(b)(i)and(ii)
canbeusedto (b)(i)warmafewdrops (b)Onlythe Aldehydesarestrongerreducingagentsthanketonesand
distinguishaldehydes ofthecompoundwith aldehydeproduces reducethemetalionandareoxidisedintheprocess
(reaction)and Tollens'reagent (i)Asilvermirror
ketones(noreaction). [ammoniacalsilver onthesideofthe i.e.RCHO+[O]==>RCOOH
nitrate] testtube.
(2)Aromatic (i)reductionofsilver(I)iontosilvermetal
aldehydesdoNOT (b)(ii)simmerwith (ii)Abrownorbrick
giveapositiveresult Fehling'sorBenedict's redppt. RCHO+2Ag++H2O==>RCOOH+2Ag+2H+
with(b)(ii)Benedict's solution[abluecomplex
orFehling'sreagent).
ofCu2+(aq)] (ii)reductionofcopper(II)tocopper(I)i.e.thebluesolution
(3)Reducingsugars oftheCu2+complexchangestothebrown/brickredcolour
mayalsogivea ofinsolublecopper(I)oxideCu2O.
positivetestwith(b)
(i)/(ii)reagente.g. RCHO+2Cu2++2H2O==>RCOOH+Cu2O+4H+
glucose(aldohexose) With(b)(i)/(ii)noreactionswithketones.
butnotfructose?
(ketohexose)?

Halogenoalkanes (i)Warmafewdropsof (i)Observecolour (i)AgNO3+RX==>RNO3?+AgX(s)


(haloalkanes) thehaloalkanewith ofprecipitateand
chemicaltestRX aqueousethanolicsilver theeffectof (ii)Thesodiumhydroxideconvertsthehalogenatominto
whereR=alkyl,X= nitratesolution,the ammoniasolution theionichalideioninahydrolysisreaction.
Cl,BrorI ethanolincreasesthe onit(forrestof
solubilityofthe detailsseethe(i) RX(aq)+NaOH(aq)==>ROH(aq)+NaX(aq)
Thehalideis immisciblehaloalkanes. notesforchloride,
covalentlybound(C bromideand thenAg+(aq)+X(aq)==>AgX(s)
Xbond),sothe (ii)Gentlysimmeringa iodidetestsabove
halogenXcannot fewdropswithaqueous ininorganic) Theadditionofdilutenitricacidpreventstheprecipitationof
reactwiththesilver NaOH(mayneedtoadd othersilversaltsorsilveroxide(e.g.Ag2Oformsifsolution
iontoformtheionic ethanoltoincrease (ii)seethe(i)notes
solubilityandreaction asaboveformore alkaline).
Ag+X(s)precipitate
untilitisconvertedto rate).Adddilutenitric details.
acidfollowedby
the'free'Xionic aqueoussilvernitrate
form.Notethat solution.
aromatichalogen
compoundswherethe
Xisdirectlyattached
tothering,doNOT
readilyhydrolysein
thiswayandnoAgX
ppt.willbeseen.
AromaticCXisa
strongerbondthan
aliphaticCX.

Esterschemicaltest Theestercanbereacted Deepredorpurple Thereactionisalsogivenbyacidchloridesandacid


RCOOR' withsaturatedethanolic colourformed.The anhydrides,andphenolsgiveapurplecolourwithiron(III)
hydroxylamine testdependson chloride,sofrankly,thetestisnotthatgood.Thistestisnot
R=H,alkyloraryl hydrochloride+20% theformationofa likelytobeexpected
methanolicKOHand hydroxamicacid
R'=alkyloraryl gentlyheateduntil RC(=NOH)OH
boiling.Thenmixture whichforms
Thereisnosimple acidifiedwith1MHCl(aq) colouredsaltswith
testforanester.
andFeCl3(aq)added Fe3+(aq)ion.
Usuallyacolourless
liquidwithapleasant dropwise.
'odour'.

Iodoformtest NaOH(aq)isaddedtoa Ayellowsolidis ThisreactionisgivenbythealcoholethanolCH3CH2OH


solutionofiodinein formedwiththe andallalcoholswiththe2olstructureCHOHCH3and
Theformationof potassiumiodide smellofan
CHI3,triiodomethane solutionuntilmostofthe antiseptic,CHI3, thealdehydeethanalCH3CHOandallketoneswiththe2
(oroldname colourhasgone.The triiodomethane, onestructureRCOCH3('methylketones')
'iodoform'. organiccompoundis meltingpoint
warmedwiththis 119oC. Itsacombinationofhalogenationandoxidationandisnota
solution. definitivetestforanything,itjustindicatesapossiblepartof
amoleculesstructure.

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