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HowtonameorganiccompoundsusingtheIUPACrules
Inordertonameorganiccompoundsyoumustfirstmemorizeafewbasic
names.Thesenamesarelistedwithinthediscussionofnamingalkanes.In
general,thebasepartofthenamereflectsthenumberofcarbonsinwhat
youhaveassignedtobetheparentchain.Thesuffixofthenamereflects
thetype(s)offunctionalgroup(s)presenton(orwithin)theparentchain.Other
groupswhichareattachedtotheparentchainarecalledsubstituents.

Alkanessaturatedhydrocarbons
Thenamesofthestraightchainsaturatedhydrocarbonsforuptoa12
carbonchainareshownbelow.Thenamesofthesubstituentsformed
bytheremovalofonehydrogenfromtheendofthechainisobtainedby
changingthesuffixanetoyl.
NumberofCarbons

Name

1
2
3

methane
ethane
propane

4
5
6

butane
pentane
hexane

7
8
9

heptane
octane
nonane

10
11
12

decane
undecane
dodecane

Thereareafewcommonbranchedsubstituentswhichyoushould
memorize.Theseareshownbelow.

Hereisasimplelistofrulestofollow.Someexamplesaregivenatthe
endofthelist.
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1.Identifythelongestcarbonchain.Thischainiscalledtheparent
chain.
2.Identifyallofthesubstituents(groupsappendingfromtheparent
chain).
3.Numberthecarbonsoftheparentchainfromtheendthatgives
thesubstituentsthelowestnumbers.Whencompairingaseriesof
numbers,theseriesthatisthe"lowest"istheonewhichcontains
thelowestnumberattheoccasionofthefirstdifference.Iftwoor
moresidechainsareinequivalentpositions,assignthelowest
numbertotheonewhichwillcomefirstinthename.
4.Ifthesamesubstituentoccursmorethanonce,thelocationof
eachpointonwhichthesubstituentoccursisgiven.Inaddition,
thenumberoftimesthesubstituentgroupoccursisindicatedbya
prefix(di,tri,tetra,etc.).
5.Iftherearetwoormoredifferentsubstituentstheyarelistedin
alphabeticalorderusingthebasename(ignoretheprefixes).The
onlyprefixwhichisusedwhenputtingthesubstituentsin
alphabeticalorderisisoasinisopropylorisobutyl.Theprefixes
secandtertarenotusedindeterminingalphabeticalorder
exceptwhencomparedwitheachother.
6.Ifchainsofequallengtharecompetingforselectionastheparent
chain,thenthechoicegoesinseriesto:
a)thechainwhichhasthegreatestnumberofsidechains.
b)thechainwhosesubstituentshavethelowestnumbers.
c)thechainhavingthegreatestnumberofcarbonatomsinthe
smallersidechain.
d)thechainhavingtheleastbranchedsidechains.
7.Acyclic(ring)hydrocarbonisdesignatedbytheprefixcyclo
whichappearsdirectlyinfrontofthebasename.
Insummary,thenameofthecompoundiswrittenoutwiththe
substituentsinalphabeticalorderfollowedbythebasename(derived
fromthenumberofcarbonsintheparentchain).Commasareused
betweennumbersanddashesareusedbetweenlettersandnumbers.
Therearenospacesinthename.
Herearesomeexamples:

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Alkylhalides
Thehalogenistreatedasasubstituentonanalkanechain.Thehalo
substituentisconsideredofequalrankwithanalkylsubstituentinthe
numberingoftheparentchain.Thehalogensarerepresentedas
follows:
F fluoro
Cl chloro
Br bromo
I

iodo

Herearesomeexamples:

AlkenesandAlkynesunsaturatedhydrocarbons
Doublebondsinhydrocarbonsareindicatedbyreplacingthesuffixane
withene.Ifthereismorethanonedoublebond,thesuffixisexpanded
toincludeaprefixthatindicatesthenumberofdoublebondspresent(
adiene,atriene,etc.).Triplebondsarenamedinasimilarwayusing
thesuffixyne.Thepositionofthemultiplebond(s)withintheparent
chainis(are)indicatedbyplacingthenumber(s)ofthefirstcarbonofthe
multiplebond(s)directlyinfrontofthebasename.
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Hereisanimportantlistofrulestofollow:
1.Theparentchainisnumberedsothatthemultiplebondshavethe
lowestnumbers(doubleandtriplebondshavepriorityoveralkyl
andhalosubstituents).
2.Whenbothdoubleandtriplebondsarepresent,numbersaslow
aspossiblearegiventodoubleandtriplebondseventhoughthis
mayattimesgive"yne"alowernumberthan"ene".Whenthere
isachoiceinnumbering,thedoublebondsaregiventhelowest
numbers.
3.Whenbothdoubleandtriplebondsarepresent,theensuffix
followstheparentchaindirectlyandtheynesuffixfollowstheen
suffix(noticethattheeisleftoff,eninsteadofene).Thelocation
ofthedoublebond(s)is(are)indicatedbeforetheparentnameas
before,andthelocationofthetriplebond(s)is(are)indicated
betweentheenandynesuffixes.Seebelowforexamples.
4.Forabranchedunsaturatedacyclichydrocarbon,theparentchain
isthelongestcarbonchainthatcontainsthemaximumnumberof
doubleandtriplebonds.Iftherearetwoormorechains
competingforselectionastheparentchain(chainwiththemost
multiplebonds),thechoicegoesto(1)thechainwiththegreatest
numberofcarbonatoms,(2)the#ofcarbonatomsbeingequal,
thechaincontainingthemaximumnumberofdoublebonds.
5.Ifthereisachoiceinnumberingnotpreviouslycovered,theparent
chainisnumberedtogivethesubstituentsthelowestnumberat
thefirstpointofdifference.
Herearesomeexamples:

Alcohols
Alcoholsarenamedbyreplacingthesuffixanewithanol.Ifthereis
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morethanonehydroxylgroup(OH),thesuffixisexpandedtoincludea
prefixthatindicatesthenumberofhydroxylgroupspresent(anediol,
anetriol,etc.).Thepositionofthehydroxylgroup(s)ontheparentchain
is(are)indicatedbyplacingthenumber(s)correspondingtothe
location(s)ontheparentchaindirectlyinfrontofthebasename(same
asalkenes).
Hereisanimportantlistofrulestofollow:
1.Thehydroxylgrouptakesprecedenceoveralkylgroupsand
halogensubstituents,aswellasdoublebonds,inthenumberingof
theparentchain.
2.Whenbothdoublebondsandhydroxylgroupsarepresent,theen
suffixfollowstheparentchaindirectlyandtheolsuffixfollowsthe
ensuffix(noticethattheeisleftoff,eninsteadofene).The
locationofthedoublebond(s)is(are)indicatedbeforetheparent
nameasbefore,andthelocationofthehydroxylgroup(s)is(are)
indicatedbetweentheenandolsuffixes.Seebelowfor
examples.Again,thehydroxylgetspriorityinthenumberingofthe
parentchain.
3.Ifthereisachoiceinnumberingnotpreviouslycovered,theparent
chainisnumberedtogivethesubstituentsthelowestnumberat
thefirstpointofdifference.
Herearesomeexamples:

Ethers
Youareonlyexpectedtoknowhowtonameethersbytheircommmon
names.Thetwoalkylgroupsattachedtotheoxygenareputin
alphabeticalorderwithspacesbetweenthenamesandtheyare
followedbythewordether.Theprefixdiisusedifbothalkylgroupsare
thesame.
Herearesomeexamples:

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Aldehydes
Aldehydesarenamedbyreplacingthesuffixanewithanal.Ifthereis
morethanoneCHOgroup,thesuffixisexpandedtoincludeaprefix
thatindicatesthenumberofCHOgroupspresent(anedialthere
shouldnotbemorethan2ofthesegroupsontheparentchainasthey
mustoccurattheends).Itisnotnecessarytoindicatethepositionofthe
CHOgroupbecausethisgroupwillbeattheendoftheparentchain
anditscarbonisautomaticallyassignedasC1.
Hereisanimportantlistofrulestofollow:
1.Thecarbonylgrouptakesprecedenceoveralkylgroupsand
halogensubstituents,aswellasdoublebonds,inthenumberingof
theparentchain.
2.Whenbothdoublebondsandcarbonylgroupsarepresent,theen
suffixfollowstheparentchaindirectlyandthealsuffixfollowsthe
ensuffix(noticethattheeisleftoff,eninsteadofene).The
locationofthedoublebond(s)is(are)indicatedbeforetheparent
nameasbefore,andthealsuffixfollowstheensuffixdirectly.
Rememberitisnotnecessarytospecifythelocationofthe
carbonylgroupbecauseitwillautomaticallybecarbon#1.See
belowforexamples.Again,thecarbonylgetspriorityinthe
numberingoftheparentchain.
3.Thereareacoupleofcommonnameswhichareacceptableas
IUPACnames.Theyareshownintheexamplesattheendofthis
listbutatthispointthesenameswillnotbeacceptedbythe
computer.Eventuallytheywillbeaccepted.
4.Ifthereisachoiceinnumberingnotpreviouslycovered,theparent
chainisnumberedtogivethesubstituentsthelowestnumberat
thefirstpointofdifference.
Herearesomeexamples:

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Ketones
Ketonesarenamedbyreplacingthesuffixanewithanone.Ifthereis
morethanonecarbonylgroup(C=O),thesuffixisexpandedtoincludea
prefixthatindicatesthenumberofcarbonylgroupspresent(anedione,
anetrione,etc.).Thepositionofthecarbonylgroup(s)ontheparent
chainis(are)indicatedbyplacingthenumber(s)correspondingtothe
location(s)ontheparentchaindirectlyinfrontofthebasename(same
asalkenes).
Hereisanimportantlistofrulestofollow:
1.Thecarbonylgrouptakesprecedenceoveralkylgroupsand
halogensubstituents,aswellasdoublebonds,inthenumberingof
theparentchain.
2.Whenbothdoublebondsandcarbonylgroupsarepresent,theen
suffixfollowstheparentchaindirectlyandtheonesuffixfollows
theensuffix(noticethattheeisleftoff,eninsteadofene).The
locationofthedoublebond(s)is(are)indicatedbeforetheparent
nameasbefore,andthelocationofthecarbonylgroup(s)is(are)
indicatedbetweentheenandonesuffixes.Seebelowfor
examples.Again,thecarbonylgetspriorityinthenumberingofthe
parentchain.
3.Ifthereisachoiceinnumberingnotpreviouslycovered,theparent
chainisnumberedtogivethesubstituentsthelowestnumberat
thefirstpointofdifference.
Herearesomeexamples:

CarboxylicAcids
Carboxylicacidsarenamedbycountingthenumberofcarbonsinthe
longestcontinuouschainincludingthecarboxylgroupandbyreplacing
thesuffixaneofthecorrespondingalkanewithanoicacid.Ifthereare
twoCOOHgroups,thesuffixisexpandedtoincludeaprefixthat
indicatesthenumberofCOOHgroupspresent(anedioicacidthere
shouldnotbemorethan2ofthesegroupsontheparentchainasthey
mustoccurattheends).Itisnotnecessarytoindicatethepositionofthe
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COOHgroupbecausethisgroupwillbeattheendoftheparentchain
anditscarbonisautomaticallyassignedasC1.
Hereisanimportantlistofrulestofollow:
1.Thecarboxylgrouptakesprecedenceoveralkylgroupsand
halogensubstituents,aswellasdoublebonds,inthenumberingof
theparentchain.
2.Ifthecarboxylgroupisattachedtoaringtheparentringisnamed
andthesuffixcarboxylicacidisadded.
3.Whenbothdoublebondsandcarboxylgroupsarepresent,theen
suffixfollowstheparentchaindirectlyandtheoicacidsuffix
followstheensuffix(noticethattheeisleftoff,eninsteadof
ene).Thelocationofthedoublebond(s)is(are)indicatedbefore
theparentnameasbefore,andtheoicacidsuffixfollowstheen
suffixdirectly.Rememberitisnotnecessarytospecifythelocation
ofthecarboxylgroupbecauseitwillautomaticallybecarbon#1.
Seebelowforexamples.Again,thecarboxylgetspriorityinthe
numberingoftheparentchain.
4.ThereareseveralcommonnameswhichareacceptableasIUPAC
names.Theyareshownintheexamplesattheendofthislistbut
atthispointthesenameswillnotbeacceptedbythecomputer.
Eventuallytheywillbeaccepted.
5.Ifthereisachoiceinnumberingnotpreviouslycovered,theparent
chainisnumberedtogivethesubstituentsthelowestnumberat
thefirstpointofdifference.
Herearesomeexamples:

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Esters
Systematicnamesofestersarebasedonthenameofthe
correspondingcarboxylicacid.Rememberesterslooklikethis:

Thealkylgroupisnamedlikeasubstituentusingtheylending.Thisis
followedbyaspace.Theacylportionofthename(whatisleftover)is
namedbyreplacingtheicacidsuffixofthecorrespondingcarboxylic
acidwithate.
Herearesomeexamples:

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Amines
Youareonlyexpectedtoknowhowtonameaminesbytheircommon
names.Theyarenamedlikeethers,thealkyl(R)groupsattachedtothe
nitrogenareputinalphabeticalorderwithnospacesbetweenthe
namesandthesearefollowedbythewordamine.Theprefixesdiand
triareusediftwoorthreeofthealkylgroupsarethesame.
NOTE:Somebooksputspacesbetweenthepartsofthename,butwe
willnot.Followtheexamples.
Herearesomeexamples:

Summaryoffunctionalgroups
Functionalgroup Prefix

Suffix

carboxylicacids

none

oicacid

aldehydes

none

al

ketones

none

one

alchols

hydroxy

ol

amines

amino

amine

ethers
fluorine

alkoxy
fluoro

ether
none

chlorine

chloro

none

bromine

bromo

none

iodine

iodo

none

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