IUPAC Nomenclature

CHE 1122-2022/ 23
Snr Prof. Vajira P. Bulugahapitiya
 Objective
•This section aims to provide knowledge on:
Rules in IUPAC Nomenclature of organic
compounds , naming organic compounds
according to IUPAC
Learning Outcomes
• Able to name organic compounds according to
the IUPAC nomenclature and vice versa
Naming of organic compounds

•In the past, the naming of organic

compounds was done based on the source it
comes, based on some characteristic
properties etc.

•These names are called as common names or

trivial names
•As number of compounds increased, and
isomers were identified, this naming is
difficult
IUPAC

• Therefore, systematic naming was developed

(end of 19th century)
• IUPAC ( International Union of Pure and Applied
Chemistry) did the task
• Names update in time intervals
• Eg: 1993 recommendation
• 2004 recommendation etc.(preferred IUPAC
nomenclature)
• 2013 –updates
• 2021 – recent updates
References

IUPAC Color Books

•
The IUPAC Color Books are the world’s authoritative resource for chemical
nomenclature, terminology, and symbols. Terminology definitions published by
IUPAC are drafted by international committees of experts in the appropriate
chemistry sub-disciplines, and ratified by IUPAC’s Interdivisional Committee on
Terminology, Nomenclature and Symbols (ICTNS). The books in this series are as
follows:
• Green Book: Quantities, Units and Symbols in Physical Chemistry
• Red Book: Nomenclature of Inorganic Chemistry
•
Blue Book: Nomenclature of Organic Chemistry
•
Purple Book: Compendium of Polymer Terminology and Nomenclature
•
Orange Book: Analytical Nomenclature
•
Silver Book: Compendium of Terminology and Nomenclature of Properties Clinical
Laboratory Sciences
•
White Book: Biochemical Nomenclature
•
Gold Book: Chemical Terminology
Rules for naming
O
4 CH2
2 6 CH3
H3C 5
1 3 7

CH3

Select the parent structure of carbon (hydrocarbon

chain)
Which is the longest chain contain maximum number of
unsaturation bonds and principle functional group

A suffix indicating major functional group of the

molecule

A prefix indicating substituent of the molecules

Numbers to locate the substituent and other essential
elements of the molecule
Example: prefix
Cl
H3C CH CH2 CH2 OH
4 3 2 1
suffix
main chain

IUPAC name: 3-chloro-1-butanol

PRINCIPLE Functional groups

Know the order of priority of the functionalities

Use the highest precedence functional group as main
functionality (suffix)

Other functionalities as prefix

Number the chain giving lowest to main functional

group

Write the number of the position of FG before suffix

 Priorirty order of fuctional groups, their abbreviation as prefix and suffix
Functional group Name of the homologous series Substituent name (prefix) Class name (suffix)

-COOH Carboxylic acid - oic acid

-COOR Ester - oate
-COCl Acid chloride - oyl chloride
-CONH2 Amide - amide
-CN Nitrile cyano nitrile
-CHO Aldehyde formyl al
-CO- Ketone oxo one
-OH Alcohol hydroxy- ol
-NH2 Amine amino amine
-F fluoro- -
-Cl chloro- -
-Br bromo- -
-I iodo- -
- NO2 nitro -
alkene (C=C) as “ene” and alkyne (C≡C) as “yne” and used as suffix.
 Main Chain with side chains
Identify the side chain and number them, giving
the lowest if no other functionalities

When more side chain, first number should be

least possible

If more than one of same side chain, use “di”,

“tri” etc.
Identify double and triple bond
Number them –head of the bond
“ene” : double bond
“yne” : triple bond

Add punctuation correctly

2,2,5-trimethyl
•Successive words are merged into one word.
• eg: 2,2,5-trimethylhexane
Arrange all as follow

Group of side chain+ secondary functional

groups+prefix of parent HC (eth, meth etc.)+
double and triple bond suffix with number +
primary functional group abbreviation suffix
with number.
O CH3
O
H3C C C C C C
OH
OH

2-hydroxy-2-methyl-5-oxohex-3-ynoic acid
4,6-dichlorohept-5-en-2-one
7-bromo-6-hydroxyheptane-2,4-dione

2-aminoethan-1-ol
Naming of Alkanes

•In straight chain alkanes, the naming is done

according to the number of carbons and the
name ends (suffix) with “ane”.
•Prefix : Meth, Eth,Prop, But, Hex, Dodec etc
according to the number of carbon in the …..
chain.
No of Carbon in IUPAC Name
alkane
1 Methane
2 Ethane
3 Propane
4 Butane
5 Pentane
6 Hexane
7 Heptane
8 Octane
9 Nonane
10 Decane
Branched Chain alkane
alkyl groups are abbreviated as following
Steps for naming alkanes
• Select the longest chain. Number the parent chain
locating least number to the alkyl side chains.

H H H H
H C C C C H 2-methylbutane
H H H
H C H
H
H H H H H
H C C C C C H 3-ethylpentane
H H H H
H C H
H C H
H
 Name following
H3C
H3C H3C CH3
H3C CH CH2 CH2 CH3
1 2 3 4 5 H3C CH CH2 CH2 CH2 CH3 H3C CH CH CH2 CH2 CH3
1 2 3 4 5 6 2 3 4 5 6
1

When there more than one alkyl of same types

Use prifix : di, tri etc.
CH3

CH3 5
CH3
3 1
C 4
2 CH3 H3C 2
H3C 6
1 CH33
H3C

2,2-dimethylpropane 3,4-diethylhexane
Cycloalkanes with substituents

Start by assigning the number 1 to

a substituted carbon so that second and third group
have as low number as possible.
5

4 CH3
1

3 2

1-ethylcyclopentane

After assigning numbers, name the compound

so that the side groups occur in alphabetical order
(NOT numbered order)
 Ring get higher priority if the same elements
are present- New recommendation

cyclobutane is senior to pentane

pentylcyclobutane
 2-methylcyclohexanol 1-ethyl-2-propylcyclohexane

1-iodo-2-propylcyclobutane
4-chloro-2-ethyl-1-methylcyclohexane
2-pentylcyopropane
NOT
2-cyclopropylpentane
 Alkenes
The suffix “ene” is used for alkene instead of “ane” in
alkanes infixed number indicating the position of the
double bonded carbon in the chain.
The chain which includes both carbon of the double
bond is selected as the parent chain.
The lowest number is given to the double bond (first
carbon of the double bond).

H3C H3C
H2C CH CH2 CH2 CH3
1 2 3 4 5 H2C CH CH CH2 CH2 CH3 H3C CH2 C CH CH2 CH3
1 2 3 4 5 6 1 2 3 4 5 6

pent-1-ene 3-methylhex-1-ene 3-methylhex-3-ene

(1-pentene) (3-methyl-1-hexene) (3-methyl-3-hexene)
 When more than one double bond is in the molecule extra
‘a’ includes to parent alkene before suffix
and diene, triene used.
3
1
4
2

Buta-1,3-diene

(1,3-butadiene)
When principle functional group present, highest number given to it
But, chain considered as the one included with double bond

H2C 2
5 CHO
3 1
H3C 4
OH

3-hydroxy-4-methylpent-4-enal
If the akane chain has more carbon

Saturated chain get seniority than chain with a double bond

Ex: Nine carbon get higher seniority than eight carbon

CH2

2 6 8
4
H3C CH3
1 3 5 7 9

4-ethenylnonane

But NOT : 3-propyloctene

Write IUPAC name for this
Cis & Trans Isomers
•Add prefix Cis or Trans and then hyphen to the name
and alkene. 4 2

1
3
cis-but-2-ene
(cis-2-butene)
trans-But-2-ene
(trans-2-butene)

Cycloalkenes
Number the cycloalkenes that gives the carbon of the
double bond the 1 and 2 positions.

cyclohexene
When alkene side chain numbering
 alkynes
Alkynes are named by replacing “ane” in alkane
by “yne”
the longest chain which includes both carbon of
the triple bond is selected.
The lowest number is given to the triple bond.

H3C

H C C H HC C CH2 CH2 CH3

1 2 1 2 3 4 5 HC C CH CH2 CH2 CH3
1 2 3 4 5 6

1-ethyne pent-1-yne 3-methylhex-1-yne

(ethyne) (1-pentyne) (3-methyl-1-hexyne)
When both types of bonds (double and triple)
is present, “ene” comes before “yne”
• When substituents are present, the lowest number is
given to the highest precedence
• When alkyl groups and halogens are present, give
lowest number to alkyne and lesser number to the
substituent according to their alphabetical order

but-3-yne-1-ol 3-chloroprop-1-yne 5-methylhex-2-yne

When double bond and tripple bond are in equivalent position,
double bonded carbon Get the lowest number

H
HC C C CH CH2
5 4 3 2 1
H

pent-1-en-4-yne

When double bond and tripple bond are in not equivalent position,
tripple bond carbon get the lowest number

O
HC C C CH CH OH
1 2 3 4 5

5-hydroxypent-4-en-1-yn-3-one
IUPAC Nomenclature of Halides
• Simply name the molecule as normal alkyl chain and
• Add the prefix fluoro, chloro, bromo, or iodo as
necessary
• Multiple groups are dichloro, trichloro etc, and
dissimilar groups are ordered alphabetically.

1-bromo-1-chloro-2,2,2-trifluoroethane

Cl Br H3C

H3C CH2 CH CH2 CH3

1 2 3 4 5 H3C CH CH CH2 CH2 CH3
1 2 3 4 5 6

3-chloropentane 2-bromo-3-methylhexane
• When parent chain has both a halo and alkyl
substituents attached to it, number the chain from the
end that the first substituent gets the lower number
regardless of whether it is halo or alkyl.
• If two substituents are in equal distance from ending
chain, then number the chain according to alphabetical
precedence.

2-chloro-4-
methylpentane
 Naming alcohol
Select the longest chain which contain –OH
group and replace “ane” by “anol” and infixed
with the number. The lowest number is given
to the carbon attached to –OH.

OH OH HO CH3
H2C CH2 CH3 H3C CH2 CH CH2 CH3
1 2 3 4 5 H3C CH HC CH CH CH3
1 2 3 1 2 3 4 5 6

propan-1-ol pentan-3-ol 3-methylhex-4-en-2-ol

(1-propanol) (3-pentanol) (3-methyl-4-hexen-2-ol)
1-(1-hydroxypropoxy)ethane-1,2-diol
 ketones
•keton group take sufix“one” replacing “e”
of alkane. The numbering of the chain
should be done giving lowest number to
the ketone carbon.
O H3C O CH3
O
H3C C CH3 C CH2 CH2 CH CH3 C
1 H3C 2 3 4 5 6 H3C CH2 C CH2
2 3 2 3 4 5
1 1
propan-2-one 5-methylhexan-2-one
(2-propanone) (5-methyl-2-hexanone) 4-methylpent-4-en-2-one
(4-methyl-4-penten-2-one )
When higher precedence group present
ketone get prefix ‘oxo”

O
2

4
OHC CH3
1 3 5

4-oxopetanal
Name following

7-bromo-6-hydroxyheptane-2,4-dione
 Naming aldehyde
• Select the longest continuous chain which contain terminal aldehyde
group and replace “ane” with “anal”. The lowest number is given to the
aldehyde carbon. Adehyde gets “1” if no functional group of higher
precedence

O H3C H3C
O O
H C CH3 C CH2 CH2 CH CH3
H 1 2 3 4 5 C CH2 CH CH CH CH3
1 2 H 1 2 3 4 5 6
Ethanal 4-methylpentanal 3-methylhex-4-en-1-al
(3-methyl-4-hexenal)
ethane-1,1,2,2-tetracarbaldehyde
•When functional group with higher
precedence present, aldehyde prefix as
“formyl” or sometime ‘oxo”

O
3
1

OHC OH
4 2

4-oxobutanoic acid

(3-formylpropanoic acid)
Nomenclature Of Carboxylic Acid
• In general carboxylic acids are named with the suffix –
oic acid by dropping final ‘e’ in corresponding alkane.
• Carboxylic carbon atom is assigned number 1.
• If there are multiple carboxyl groups on the same
parent chain, suffix dicarboxylic, tricarboxylic etc can be
used. O
H H H

H C C C C OH
butanoic acid
H H H

O H H

HO C C C F 3-fluoropropanoic acid
H H
Name following compounds
2-hydroxyethoxyethanoic acid
IUPAC Nomenclature Of Ethers
• Ethers are named as an alkoxyalkanes. “ROR”
• The shorter of the two alkyl chains becomes the first
part of the name with the ‘ane’ suffix changed to oxy
and the alkane chain becomes the suffix of the name
of ether.

O methoxymethane

O methoxyethane
Naming of esters
• Esters, RC(O)OR’ are named as alkyl
derivatives of carboxylic acids.

• The alkyl (R’) group is named first

followed by space

• The RC(O)-O part is then named as

separate word based as carboxylic acid
name with the ending changed from –oic
to oate.
 Main Branch

O
H H H H H Secondary
H C C C C C O C H Branch
H H H H H

pentanoate
methyl
methyl pentanoate
Name following
H3C O
O
H3C CH2 CH2 CH2 CH C
H3C CH2 C OCH3 6 5 4 3 2 1
3 2 1 OCH2CH3
 IUPAC Nomenclature of Amides
• Amides take the suffix “amide” dropping the ‘-oic acid’
in the name of acid.

propanamide

• In case of Secondary and tertiary amine group in amide,

alkyl groups bonded to Nitrogen atom are treated as
substituent with the location prefix N, or N,N-

N,N-dimethylmethanamide
IUPAC Nomenclature of Acid Chloride and
Anhydrides

• Acid chlorides are named by dropping –oic acid

from the name and the adding –oyl chloride

butanoyl chloride

• Many anhydrides are named by dropping the word

acid from the name of carboxylic acid and adding
the word -oic anhydride. (Two words).

propanoic anhydride
 IUPAC Nomenclature Of Amine
• Amines are named for the attached alkane chain with
the Suffix “amine” and elision of the final ‘e’.
• If necessary, bonding position is infixed.
H H

H C N

H H
methanamine N-methylethanamine
• For Secondary amines, the longest carbon chain
attached to the nitrogen becomes the primary name
of amine; the other chain is prefixed as an alkyl group
with location prefix given as a N.
 IUPAC Nomenclature Of Nitriles

• Acyclic Nitriles are named by adding the suffix ‘nitrile’

to the name of the corresponding hydrocarbon.

ethanenitrile
butanenitrile
 Cyclic alkanes
• Cyclic alkanes are simply prefixed with cyclo-
• Prefix is add to the front of the name of the longest
chain

cyclohexane

cyclooctane

cyclohexene
Cyclic aldehydes
• suffix carbaldehyde is used

cyclopentanecarbaldehyde
Carboxylic acids
 Cyclic carboxylic acid esters

4-chloro-pyridine-2-carboxylic acid methyl ester

 Bicyclic Compounds
• Compounds containing two fused or bridged rings are
named as the name of the bicycloalkanes.
• The name of the alkane corresponding to the total
number of carbon atoms in the rings is taken as the
parent name.

Contains seven carbon atoms

and is, therefore, a
bicycloheptane.
 Bicyclic Compounds

•Interpose an expression in
brackets within the name that
denotes the number of carbon
atoms in each bridge (in order
of decreasing length).
Bicyclo[2.2.1]heptane

•There are fused rings with

zero carbons in the bridge too.

Bicyclo[1.1.0]butane
Tricyclic - refer

tricyclo[4.3.2.1]dodecane
 • If substituents are present, number the bridged ring
system beginning at one bridgehead, proceeding first
along the longest bridge to the other bridgehead,
then along the next longest bridge back to the first
bridgehead. The shortest bridge is numbered last.

8-methylbicyclo[3.2.1]octane

8-methylbicyclo[4.3.0]nonane
 Spirocyclic Compounds
• Bicyclic organic compounds with rings connected through
just one atom are called Spiro compounds.
• The root name is based on the number of C atoms in the ring
structure.
• The prefix Spiro is added at the beginning of the name and
the size of the rings (number of C atoms in each ring) is
indicated in square brackets where the smallest is indicating
first.
• The rings are numbered starting on the smallest ring
adjacent to spirocenter.
8 1
7 4
2 spiro[3.4]octane
6 5 3
•Name these:

spiro[2.7]decane

6-methylspiro[3.5]nonane
 Naming of aromatic compounds

• Numbering is giving lowest to main functional group

Problem : Name following compounds

70
Draw the structures of following compounds

•4,4-difluoro-3-methylbut-1-ene
•5-methylcyclopenta-1,3-diene
•N,N-dimethylbut-3-en-2-amine
•2,2-dimethyl-3,4-dioxobutanoic acid
•2-aminocyclobutanol