Download Handout: Naming Organic Compounds Substituents Longest carbon

Handout:NamingOrganicCompounds
A.IUPACNaming
GeneralRules:
Prefix+Parent+Suffix
Family
Substituents
Longestcarbonchain
SomeSubstituentNames
Substituent
Substituent
Group
Name
Hydrocarbon
alkyl
withsingle
bondsonly
1. Nameparent+suffix:longestcarbonchain+familysuffix.
2. Numbercarbonsinparentchain:Beginnumberingfromend
thatmeetsspecifiedcriteria(*SeeNomenclatureChart).
3. Nameprefix:substituentposition#sandnames(group
repeatedsubstituentstogetherusingdi-,tri-,etc).
4. Writefullname,listingsubstituentsinalphabeticalorder
(ignoredi-,tetra-inalphabetizing).
H 3C
C
H
H 3C
C
H
CH 3
H 3C
C
H
H2
C
H2
C
CH 3
sec-butyl
C
CH 3
–OR
O
HC
O
tert-butyl
O
acyl
O
C
C
H 3C
C
(Endswith–oyl, H 3C
H2
exceptfor
acetylpropanoyl
acetyl)
H2
alkoxy
H 3C
C
H 3C
O
C
Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane
CH 3
H 3C
R
Name
H 3C C
methylethyl
CH 3
SomeParentAlkaneNames
No.of
Structure
Carbons
1
CH4
2
CH3CH3
3
CH3CH2CH3
4
CH3CH2CH2CH3
5
CH3CH2CH2CH2CH3
6
CH3CH2CH2CH2CH2CH3
7
CH3CH2CH2CH2CH2CH2CH3
8
CH3CH2CH2CH2CH2CH2CH2CH3
9
CH3CH2CH2CH2CH2CH2CH2CH2CH3
10
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
H2
H 3C
isopropylisobutyl
NameFormat:#–substituent–#–substituentparentsuffix
SpecificExamples
formyl
methoxyethoxy
keto
hydroxy
nitro
amino
halo
-Clchloro-Brbromo
-Iiodo
C
–OH
-NO2
–NH2
-X(halogen)
phenyl
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B.CommonNames
Frequently-UsedCommonNames
Compound
CommonName
CH2=CH2
ethylene
CH3CH=CH2
propylene
HC
CH acetylene
O
acetone
C
CH 3
H 3C
O
CH2
O
CH
H 3C
O
HC
OH
O
H 3C
C
OH
O
H 3C
C
H2
C
OH
O
H 3C
H2
C
C
H2
C
OH
IUPACName
1-ethene
1-propene
1-ethyne
2-propanone
formaldehyde
methanal
acetaldehyde
ethanal
formicacid
methanoicacid
aceticacid
ethanoicacid
propionicacid
propanoicacid
butyricacid
butanoicacid
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NomenclatureChartforOrganicCompounds(FromHIGHESTTOLOWESTnamingpriority)
FAMILY
Carboxylicacid
PARENT
SUFFIX
NUMBERING
Parentislongest
carbonchain
containingcarboxylic
acid.Derivename
fromparentalkane.
–oicacid
(-dioicacid
fordicarboxylicacid;
-enoicacid
forunsaturatedacid)
BeginatcarbonylC. Commonnamesareoftenused
(CnexttoCOOHgroupis
designatedas“α”).
[Salts:cation+namederived
fromparentacid,replacing–ic
acidwith–ate]
NOTES
EXAMPLES
O
H
C
H 3C
C
OH
Cl
2-chloropropanoicacidor
α-chloropropionicacid(common)
O
HO
O
H2
C
C
OH C
propanedioicacid
Ester
NameofalkylgroupR’ –ate
in-COOR’+Nameof
acylgroup(derived
fromparentacid,
replacing–icacidwith
–ate)
Amides
Derivenamefrom
parentcarboxylicacid,
replacing–oicacid
with–amide.
Derivenamefrom
parentalkane.Parent
alkaneislongestCchaincontaining
carbonyl.
Derivenamefrom
parentalkane.Parent
alkaneislongestCchaincontaining
carbonyl.Parentname
startswithposition#
ofcarbonylC.
Parentislongest
carbonchain
containingOH.Parent
namestartswith
position#oftheC
withOH.
Aldehydes
Ketones
Alcohol
–amide
–al
–one
–ol
(-diol,
-triol,etc.)
Numberalkyl
groupR’andacyl
groupseparately.
ForR’,begin
numberingatend
nearertocarbonyl
C.Forparent,begin
numberingat
carbonylC.
BeginatcarbonylC.
O
Commonnamesareoftenused:
H2 H2
H2
nameofalkylgroupthat
H 3C
C C C O C CH 3 replaced-Hin-COOH+name
ethylbutanoateor
derivedfromcommonnameof
ethylbutyrate(common)
parentacid,replacing–icacid
with–ate
Alkylsubstituentsonnitrogen
startwith“N-.”
H 3C
Beginatendnearer Commonnamesareoftenused
tocarbonylC.
forsimpleketones:namesof
twoalkylgroups+“ketone.”
Beginatendnearer Cyclicalcohols:Parentname
toOHgroup.
beginswith“cyclo”(noneedto
startparentnamewith“1”).
BeginnumberingatCwithOH,
andnumbertogive
substituentslowestnumbers.
CH 3
C
N
CH 3
N,N-dimethylacetamide
BeginatcarbonylC. Commonnamesareoftenused
forsimplestaldehydes,ending
with“–aldehyde.”
O
CH 3
H 3C
C
H
O
H2
C
C
H
3-methylbutanalor
β-methylbutyraldehyde(common)
O
H2
C
H2
C
H 3C
C CH 3 2-pentanoneor
methylpropylketone(common)
CH 3
H 3C
C
H
OH
H2
C
C
H
H2
C
5-methyl-3-hexanol
CH 3
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OH
CH 3
2-methylcyclohexanol
OH
H 3C
FAMILY
Thiols
PARENT
SUFFIX
NUMBERING
NOTES
–thiol
Amines
–amine
Nameinsamewayasalcohols,
exceptendwith“-thiol.”
1°amines,and2°,3°amines
withsameRgroupsonN:Treat
alkylgroupsattachedto
nitrogenassubstituents.For
samesubstituents,use“di”and
“tri.”
2°,3°amineswithdifferentR
groupsonN:Parentamineis
theonewithlargestRgroup;
nameothergroupsas
substituents,startingwithN-.
[Ionsderivedfromamines:
Replace–aminewith
–ammonium.]
Cyclicalkenes:Parentname
beginswith“cyclo”(noneedto
startparentnamewith“1”).
Numbermultiplebonds1and
2,indirectiontogivefirst
substituentthenextsmaller
possiblenumber.
Alkenes
Alkynes
Alkanes
Parentislongest
carbonchain
containingthedouble
ortriplebond.Parent
namestartswith
positionnumberof
multiplebond.
Mayneedcis/trans
designation.
–ene
–yne
(-diene,
-triene,etc.)
Parentislongest
carbonchain.
–ane
Beginatendcloser
tomultiplebond.
(Ifmultiplebonds
areequidistant,
givesmaller
numbertofirst
branchpoint).
Thengivesmallest
numberspossible
tosubstituents.
Beginatendnearer
tobranchpoint.
Thengivesmallest
numberspossible
tosubstituents.
H2
C
C
H
H2
C
OH
1,3-butanediol
EXAMPLES
Cyclicalkanes:Parentname
beginswith“cyclo.”Give
smallestnumbertosubstituent
thatcomesfirstinalphabetical
order.Numberindirectionto
givesecondsubstituentthe
smallerpossiblenumber.(If
singlesubstituent,don’tneed
“1-.”)
H 3C
H2
C
SH
H2
C
H 3C
ethanethiol
H2
C
NH 2
(1°)
propylamine
H 3C
H2
C
H2
C
N
H 2C
CH 3
CH 3
triethylamine
(3°withsameR
groups)
H2
C
H 3C
H2
C
H
N
(2°with
diff’tRgroups)
N-methylpropanamine
H 3C
H2
C
CH 3
CH2CH2CH 3
C
C
H
CH 3
cis-4-methyl-3-heptene
H 3C
H2
C
H2
C
H2
C
C
C
H2
C
H
C
H2
C
CH 3
CH 3
2-heptyne
CH 3
4-methylcyclohexene
CH 3
H 3C
C
H
H 2C
CH 3
4-ethyl-2-methylhexane
H 3C
H2
C
CH 3
1-ethyl-3-methylcyclohexane
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FAMILY
Ethers
PARENT
SUFFIX
NUMBERING
NOTES
EXAMPLES
Thealkoxygroup–OR
istreatedasthe
substituent(Alkaneor
anotherfunctional
groupistheparent).
Commonnamesareoftenused
forsimpleethers:twoRgroups
+“ether.”
Commonnamesareusedfor
cyclicethercompounds.
CH 3 1-ethoxypropaneor
ethylpropylether(common)
H 3C
H2
C
O
H 3C
H2
C
O
H2
C
H2
C
H2 H2 H2
C C C
OH
3-ethoxypropanol
Haloalkanes(or
AlkylHalides)
Halogenatomis
treatedassubstituent
(Alkaneoranother
functionalgroupisthe
parent).
Commonnamesareoftenused
forsimplehaloalkanes,in
format“alkylhalide.”
H 3C
H2
C
Br
1-bromoethaneor
ethylbromide(common)
AromaticNomenclature
FAMILY
Aromatic
(Benzenecontaining)
PARENT
“benzene”orcommon
nameforsubstituted
benzene
SUFFIX
NUMBERING
NOTES
Fordi-substituted
Commonnamesformonobenzenes:o,m,p
substitutedbenzenesareoften
systemistypically
used:
O
O
used,with
substituentslisted
C OH
CH
inalphabetical
order.(Ifusing
numbering,
BenzoicAcidBenzaldehyde
numberby
alphabetical
NH 2
OH
priorityof
substituents.)
PhenolAniline
o-
CH 3
Toluene
m-
Ifcommonnameofmonsub’d
benzeneisusedasparentand
thereare>2substituents,the
carbonbearingthefunctional
p-
groupoftheparentisnumbered
1,thennumberindirectionto
givesubstituentslowestnumbers
possible.
EXAMPLES
NO 2
nitrobenzene
NO 2
Cl m-chloronitrobenzeneor
1-chloro-3-nitrobenzene(IUPAC)
OH
O2N
p-nitrophenolor
1-hydroxy-4-nitrobenzene(IUPAC)
NO 2
Cl
OH
2-chloro-4-nitrophenol
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