11/2/2016 interpretinginfraredspectra

INTERPRETINGANINFRARED
SPECTRUM

Thispageexplainshowtouseaninfraredspectrumtoidentify
thepresenceofafewsimplebondsinorganiccompounds.

Note:Thispagefollowsdirectlyonfromtheintroductory
pageoninfraredspectra.Ifyouhaven'talreadydoneso,you
shouldreadthatpagebeforeyougoon.

Theinfraredspectrumforasimplecarboxylicacid

Ethanoicacid

Ethanoicacidhasthestructure:

Youwillseethatitcontainsthefollowingbonds:

carbonoxygendouble,C=O

carbonoxygensingle,CO

oxygenhydrogen,OH

carbonhydrogen,CH

carboncarbonsingle,CC

Thecarboncarbonbondhasabsorptionswhichoccurovera
widerangeofwavenumbersinthefingerprintregionthat
makesitverydifficulttopickoutonaninfraredspectrum.

Thecarbonoxygensinglebondalsohasanabsorbtioninthe
fingerprintregion,varyingbetween1000and1300cm1
dependingonthemoleculeitisin.Youhavetobeverywary
aboutpickingoutaparticulartroughasbeingduetoaCO
bond.

Note:Ifyouaren'tsurewhatthefingerprintregionis,follow
thislinkbeforeyougoon.

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11/2/2016 interpretinginfraredspectra

Theotherbondsinethanoicacidhaveeasilyrecognised
absorptionsoutsidethefingerprintregion.

TheCHbond(wherethehydrogenisattachedtoacarbon
whichissinglybondedtoeverythingelse)absorbssomewhere
intherangefrom28532962cm1.Becausethatbondis
presentinmostorganiccompounds,that'snotterriblyuseful!
Whatitmeansisthatyoucanignoreatroughjustunder3000
cm1,becausethatisprobablyjustduetoCHbonds.

Thecarbonoxygendoublebond,C=O,isoneofthereally
usefulabsorptions,foundintherange16801750cm1.Its
positionvariesslightlydependingonwhatsortofcompounditis
in.

TheotherreallyusefulbondistheOHbond.Thisabsorbs
differentlydependingonitsenvironment.Itiseasilyrecognised
inanacidbecauseitproducesaverybroadtroughintherange
25003300cm1.

Note:Youwillneverhavetorememberwherethese
absorptionsoccur.Youwillalwaysbegiventhisdatainan
A'levelexam.

Theinfraredspectrumforethanoicacidlookslikethis:

ThepossibleabsorptionduetotheCOsinglebondisqueried
becauseitliesinthefingerprintregion.Youcouldn'tbesurethat
thistroughwasn'tcausedbysomethingelse.

Note:Theinfraredspectraonthispagehavebeenproduced
fromgraphstakenfromtheSpectralDataBaseSystemfor

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11/2/2016 interpretinginfraredspectra

OrganicCompounds(SDBS)attheNationalInstituteof
MaterialsandChemicalResearchinJapan.

Itispossiblethatsmallerrorsmayhavebeenintroduced
duringtheprocessofconvertingthemforuseonthissite,
butthesewon'taffecttheargumentinanyway.

Theinfraredspectrumforanalcohol

Ethanol

TheOHbondinanalcoholabsorbsatahigherwavenumber
thanitdoesinanacidsomewherebetween32303550cm1.
Infactthisabsorptionwouldbeatahighernumberstillifthe
alcoholisn'thydrogenbondedforexample,inthegasstate.All
theinfraredspectraonthispagearefromliquidssothat
possibilitywillneverapply.

NoticetheabsorptionduetotheCHbondsjustunder3000cm
1,andalsothetroughsbetween1000and1100cm1oneof
whichwillbeduetotheCObond.

Theinfraredspectrumforanester

Ethylethanoate

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ThistimetheOHabsorptionismissingcompletely.Don't
confuseitwiththeCHtroughfractionallylessthan3000cm1.
ThepresenceoftheC=Odoublebondisseenatabout1740
cm1.

TheCOsinglebondistheabsorptionatabout1240cm1.
Whetherornotyoucouldpickthatoutwoulddependonthe
detailgivenbythetableofdatawhichyougetinyourexam,
becauseCOsinglebondsvaryanywherebetween1000and
1300cm1dependingonwhatsortofcompoundtheyarein.
Sometablesofdatafineitdown,sothattheywilltellyouthatan
absorptionfrom12301250istheCObondinanethanoate.

Theinfraredspectrumforaketone

Propanone

Youwillfindthatthisisverysimilartotheinfraredspectrumfor
ethylethanoate,anester.Again,thereisnotroughduetotheO

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11/2/2016 interpretinginfraredspectra

Hbond,andagainthereisamarkedabsorptionatabout1700
cm1duetotheC=O.

Confusingly,therearealsoabsorptionswhichlookasifthey
mightbeduetoCOsinglebondswhich,ofcourse,aren't
presentinpropanone.Thisreinforcesthecareyouhavetotake
intryingtoidentifyanyabsorptionsinthefingerprintregion.

Aldehydeswillhavesimilarinfraredspectratoketones.

Theinfraredspectrumforahydroxyacid

2hydroxypropanoicacid(lacticacid)

ThisisinterestingbecauseitcontainstwodifferentsortsofOH
bondtheoneintheacidandthesimple"alcohol"typeinthe
chainattachedtotheCOOHgroup.

TheOHbondintheacidgroupabsorbsbetween2500and
3300,theoneinthechainbetween3230and3550cm1.Taken
together,thatgivesthisimmensetroughcoveringthewhole
rangefrom2500to3550cm1.Lostinthattroughaswellwillbe
absorptionsduetotheCHbonds.

NoticealsothepresenceofthestrongC=Oabsorptionatabout
1730cm1.

Theinfraredspectrumforaprimaryamine

1aminobutane

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11/2/2016 interpretinginfraredspectra

PrimaryaminescontaintheNH2group,andsohaveNH
bonds.Theseabsorbsomewherebetween3100and3500cm1.
Thatdoubletrough(typicalofprimaryamines)canbeseen
clearlyonthespectrumtotheleftoftheCHabsorptions.

Questionstotestyourunderstanding

Ifthisisthefirstsetofquestionsyouhavedone,pleasereadthe
introductorypagebeforeyoustart.YouwillneedtousetheBACKBUTTON
onyourbrowsertocomebackhereafterwards.

questionsoninterpretingIRspectra

answers

Wherewouldyouliketogonow?

Totheinfraredspectroscopymenu...

Totheinstrumentalanalysismenu...

ToMainMenu...

JimClark2000(modifiedAugust2014)

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