Examiners Report

January 2017

GCE Chemistry (WCH05) Paper 01

General Principles of Chemistry II
Transition Metals and Organic
Nitrogen Chemistry (including
synoptic assessment)
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General

Somecandidateswereverywellpreparedforthisexaminationandscoredhighmarks.Many
candidateswereabletodemonstratethattheyhadasoundknowledgeofthetopicsinthe
specificationandcouldapplythistothequestionswithjustafewerrorsoromissions.Some
candidateswouldbenefitfrommuchmorepreparationtoensurethattheyknowthebasicfacts,can
expresstheirideasclearlyandcarryoutcalculations,showingtheirworking.

SectionA

Themeanmarkforthemultiplechoicequestionswas12.37,whichisslightlylowerthanforsome
pastpapers.Thehighestscoringquestionswere1and5,withover80%ofcandidatesachieving
thesemarks.Themostchallengingquestionwas20,with26%ofcandidatesachievingthismark.

SectionB

Question21

Themajorityofcandidatesarefamiliarwiththemechanismforthenitrationofbenzene.Some
candidateswereunabletowriteabalancedequationfortheformationoftheNO2+electrophileand
otherswereunsureaboutwhattheelectrophilewassoneutralspeciesandnegativeionswereseen.
Othercommonerrorsincludedpoorlydrawncurlyarrows,thehorseshoeintheintermediatenot
facingthetetrahedralcarbonatom,thepositivechargenotwithinthehorseshoe,addingan
additionalchargetotheNO2grouporthehydrogenatomintheintermediateanddrawingacurly
arrowstartingfromthehydrogenatominsteadoftheCHbond.

ManycandidateswereabletoidentifythereagentsneededinStep2ofthereactionscheme.
However,manycandidatesdidnotrealisethatthetemperatureinStep3shouldnotbehigherthan
10oCotherwisethebenzenediazoniumchloridewilldecompose.Somecandidatesthoughtthatthe
sodiumnitriteorphenylaminewoulddecomposeabovethistemperatureandafewjustreferredto
thecompounddecomposing,withoutstatingwhichcompound.Afewcandidatesthoughtthatthere
wouldbemultiplesubstitutionsatahighertemperature.

Manycandidatescoulddrawthestructureofbenzenediazoniumchloridebutaminorityincludeda
bondbetweenanitrogenatomandthechlorideion.Thereweremanycorrectanswersforpart(v),
althoughsomecandidateswerecarelessinshowingtheHoftheOHgroupattachedtothebenzene
ring.Thereagentandconditionsforthepreparationofmethylbenzenefrombenzenewereusually
wellknown,althoughasmallnumberreferredimpreciselytochloroalkaneorhaloalkane.

Thereweresomeexcellentanswerstopart(c)thatscoredfullmarks.Somecandidateslostmarks
byomittingsmalldetailsbutanumberwereunabletostartthesynthesis.Commonerrorsincluded:
juststatingpotassiumdichromate(VI)fortheoxidisingagentandomittingtheacid,omittingthedry
etherfromlithiumtetrahydridoaluminate(III),notshowinghowtoformphenylmethanolfrom
benzaldehyde,usingphenolinsteadofphenylmethanolasthealcoholandomittingtheadditionofa
strongacidduringtheesterificationwhenusingbenzoicacidandphenylmethanol.Somecandidates
includedanextrastepinwhichtheyconvertedbenzoicacidtobenzoylchlorideandthiswas
acceptable.

Question22
Manycandidatesscored1markforonecorrectelectronicconfigurationin(a)(i).Asignificant
numberofcandidatesshowedelectronslostfromthe3dorbitalsinthetwoionsandleftoneortwo
electronsinthe4sorbital.Manycandidatesknewthattransitionelementformsoneormorestable
ionswithanincompletedsubshellbutonlyasmallminorityrealisedthatinadblockelement,itis
thelastelectrontobeaddedthatentersadorbital.Thereweremanyanswersthatincorrectly
statedtheouterelectronisinthedsubshell.

Part(a)(iii)waspoorlyanswered.Manycandidatesdidnotrelatetheiranswerstothestabilityofa
halffulldsubshellofelectrons.Somecandidateswroteaboutpartiallyfilleddorbitalswhenthey
clearlymeanthalffilled.Therewasalsoconfusionbetweenorbitalsandsubshellsassome
candidateswroteaboutthestabilityofahalffulldorbital.Candidatesshouldbeencouragedto
refertothedsubshelltoavoidtheproblemofjustmentioningonedorbital.

Manycandidatesdidrealisethattheionshavedifferentcoloursinaqueoussolutionastheligands
willcausedifferentsplittingofthedorbitalssotheelectronswillabsorbdifferentfrequenciesof
lightwhentheyareexcitedfromalowerenergydorbitaltoahigherenergydorbital.Some
candidatesjustmentionedabsorbingenergy,colourorlightandafewcandidatesthoughtthere
weredifferentligandspresentinthecomplexions.Thereweresomeanswerswhichshowedthe
candidateswereconfusedwithemissionspectra.

Somecandidatesgaveclearexplanationsofhowtheydeducedthefinaloxidationnumberof
manganese.Othersgaveajumbleofnumbersandfinallywrotedownthecorrectanswerora
differentnumber.Candidateswereonlyawardedamarkiftheygavesomecorrectexplanation
basedonthedatagiveninthequestion.Somecandidatesdidnotlookcarefullyattheformulafor
arsenic(III)oxideandtheythoughtthattherewasjustonearsenicatomineachformulaandfiveof
theselost10electrons.Afewcandidatesdeducedthetwohalfequationsandtheoverallequation
betweenpotassiummanganate(VII)andarsenic(III)oxideandtheywereawardedfullmarks.

Themajorityofcandidatescouldgivethemeaningofbidentateligandalthoughsomereferredto
twoligandsorimpliedthatoneligandformedadoublebondtothemetalionandothersjuststated
thattheligandhastwolonepairsofelectronsbutdidnotmentionusingthemtoformbondstothe
metalion.However,onlyasmallminoritywereabletodeducethestructuresofthetwobidentate
ligands.Manycandidatesscored1markforthestructureof1,2diaminocyclohexanebutthe
majorityofcandidatesdidnotputthenegativechargesontheethanedioateion.Theoxidation
numberofplatinumwasoftenincorrect.Somecandidatesignoredtheinformationinthefirstline
of(c)thattoldthemthattheplatinumisanionandtheywrote0astheoxidationnumber.

Question23

ManycandidatescouldsuggestsuitablereagentsforSteps2and3.However,themajorityof
candidatesseemedunfamiliarwiththereactionbetweenanamineandchloroethanesotheywere
unabletodrawacorrectorganicproductin(a)(iii).Manyincorrectstructuresshowingachlorine
atomoranestergroupwereseen.

Thezwitterionoftyrosinewasoftencorrect,althoughsomecandidatesomittedtheOHonthe
benzeneringorchangeditintoanionandothersomittedtoprotonatetheNH2group.Thetwo
opticalisomerswereoftencorrect,althoughcandidatesshouldbeadvisedtojustdrawthemas
mirrorimagesofeachotherandnottoswapanothertwogroupsaroundandgivetheoriginal
moleculeagain.Manycandidateswereabletodrawthepolyamideformedfromtyrosine,although
somedidnotdisplaytheamidelinkage,someaddedanextraoxygenatominthelinkageandothers
drewmorethantworepeatunits.Candidatesfounditmuchmoredifficulttodrawthepolyester
formedfromserineandmanydrewanotherpolyamide.

Part(c)wasdifficultandwasintendedtotestcandidatesabilitytoapplytheirknowledgetoanew
reaction.Itwaspleasingthatmanycandidateswereabletodrawthestructuresofthecorrect
aldehydeandaminoacid.Manycandidatesthoughtthatitwasnotpossibletodistinguishbetween
tyrosineandserinebytheirinfraredabsorbanceinthe4000to2000cm1rangeastheyjuststated
thattheaminoacidshavethesamefunctionalgroups.However,theyshouldhaveconsideredthe
absorbancefromtheCHbondsinthearenegroupintyrosinethatisnotpresentinserine.

Candidatesfoundpart(e)morechallengingthanexpected.Manycandidateswereunabletowork
outthecorrectsplittingpatternsandsomequotedthechemicalshiftfortheOHprotonasthatofan
alcoholinsteadofacarboxylicacid.

Question24

Manycandidatescoulddrawanacceptabledotandcrossdiagramforasulfate(VI)ion,although
somecandidatesshowedthreeorfourdoublebonds,someincludedalonepairofelectronsonthe
sulfuratomandothersomittedtheadditionaltwoelectronsfromthe2charge.Afewcandidates
justdrewbondsanddidnotincludetheelectrons.Theshapeoftheionwasusuallycorrect.

Manycandidatescouldcompletethecalculationin(a)(iii)correctly.Commonerrorsincluded
stoppingafterjustworkingoutthenumberofmolesoflead(II)sulfate(VI)addedandrounding
numberstooearlyinthecalculation,e.g.9.55395x103roundedto1x102.

Candidateswereunabletowritethebalancedequationsin(b).Somecandidateswereunabletowrite
thecorrectformulaeforsodiumdisulfate(VI)andsodiumsulfate(VI),eventhoughtheformulaeofthe
ionsweregivenintheinformationatthestartofthequestion.Theformulaforammonium
dichromate(VI)wasoftenincorrectand(NH3)2Cr2O7wasacommonerror.Somecandidatesgavethe
correctformulaebutomittedtobalancetheequation.

ManycandidateswereabletoselectthecorrectvalueforEotocompletethetablebuttheydidnot
givethecorrecthalfequation.Acommonerrorwastoomittheelectronsorincludeanincorrect
numberofelectrons.Manycandidateswereabletodeducethecorrectspeciesofthestrongest
oxidisingagent,althoughsomegavethehalfequationanddidnotstatewhichspeciesinthe
equationistheoxidisingagent.Manycandidateswereunabletoselectthetwohalfequationsthat
involvedthemanganate(VI)ionandonlyasmallnumberwereabletoaddthemcorrectlysothatthe
electronscancelled.TheEocellvaluewassometimescorrectbutmanycandidatesgavethewrong
sign,addedthevaluesforthehalfcellsinsteadofsubtractingthemorusedthewrongvalueforthe
hydrogenperoxidehalfcell.

Aminorityofcandidatesdrewcleardiagramsoftheapparatususedtodeterminethestandard
electrodepotentialofthedichromate(VI)/chromium(III)electrode.Themostcommonomissionwas
notaddingacidtothedichromate(VI)/chromium(III)halfcell.Othercommonerrorsincluded:
addingacelltothecircuit,nothavingacompletecircuitastherewasnosolutioninatleastone
beakerortheend(s)ofthesaltbridgewerenotinthesolution(s),usingachromiumelectrode
insteadofplatinum,puttingchromium(III)inonebeakeranddichromate(VI)inaseparatebeaker
andnotincludingtheconcentrationsofsolutionsorthepressureofhydrogen.

OnlyabouthalfofthecandidateswereabletodeducethemoleratioofS2O32:Cr2O72fromtwoof
theequationsgiven.Thereweresomeexcellentanswerstothefinalunstructuredredoxtitration
calculations,withtheworkingclearlyexplained.Allcandidatesshouldhavebeenabletoscoretwo
marksforcalculatingthemolesofthiosulfateionsandtheinitialmolesofdichromate(VI)ionsbut
somedidnotattemptthesesteps.Commonerrorsincluded:omissionofthesubtractionto
determinethenumberofmolesofdichromate(VI)ionsthatreactedwithethanol,notusingthe
dilutionfactorandusinganincorrectmolarmassforethanol.

Inordertoimprovetheirperformance,candidatesshould:

readthequestioncarefullyandmakesurethatyouareansweringthequestionthathas
beenasked
learnthemeaningsofallthekeytermsinthespecification
showallyourworkingforcalculations
practisewritingformulaeofcompounds
checktomakesurethatequationsarebalanced
practisecombininghalfequationstogiveanoverallequationforareaction
drawalloftheatomsandbondsondisplayedformulaeoforganiccompounds
becarefulhowyoudrawcurlyarrowsinorganicmechanisms
revisethereactionbetweenaminesandhalogenoalkanes
revisehowtodrawthestructureofapolyester
practisedrawingdiagramsofelectrochemicalcells.