IUPAC Nomenclature of Organic Compounds

International Union of Pure and Applied Chemistry (IUPAC) is a body

of International Council of Science Union (ICSU) that coordinates activities related
with chemical sciences. It was formed in 1919.

ICSU is a non-governmental organization to promote international scientific activities

in different branches of science.

The purpose of IUPAC system of nomenclature is to establish an international

standard of naming compounds.

Fundamental principle is to identify the longest chain of carbon atoms connected by

single bond in acyclic or ring.

Discussion in the class ----

The name of every organic molecule has 3 parts:
1. The parent name indicates the number of carbons in the longest continuous chain.
2. The suffix indicates what functional group is present.
3. The prefix tells us the identity, location, and number of substituents attached to the
carbon chain.
 The Parent
The “parent” part of the name tells you how many carbons are in the longest chain “main chain”
of the molecule.

Alkane chain # Carbons Parent

C 1 meth
C-C 2 eth
C-C-C 3 prop
C-C-C-C 4 but
C-C-C-C-C 5 pent
C-C-C-C-C-C 6 hex
C-C-C-C-C-C-C 7 hept
C-C-C-C-C-C-C-C 8 oct
C-C-C-C-C-C-C-C-C 9 non
C-C-C-C-C-C-C-C-C-C 10 dec
C-C-C-C-C-C-C-C-C-C-C 11 undec
C-C-C-C-C-C-C-C-C-C-C-C 12 dodec
 The Suffixes
Suffixes on the end of the name of an organic molecule tell you what major family the
molecule belongs to

Primary suffix: It indicates the nature of the carbon atom chain selected.
Secondary suffix: This is the word that defines the ‘family’ or functional group in
the organic compound.

Functional Group Class of compound Suffix

-C-C- alkane -ane
-C=C Alkene -ene
Primary suffix
-C≡C- Alkyne -yne
-COOH Carboxylic acids -oic acid
-COOR Ester -oate
-COX (X=F, Cl, Br, I) Acyl halides -oyl halide
-CONH2 Acid amide -amide
Secondary suffix
-CN Nitriles -nitrile
-CHO Aldehyde -al
>C=O Ketones -one
-OH Alcohol -ol
-NH2 Amine -amine
 Prefixes
Prefixes are any substituent attached to the main chain (parent) of the molecule.

Functional Group Class of compound Suffix

CH3- methyl
CH3CH2- ethyl
CH3CHCH3 isopropyl or i-propyl
(CH3)3C- tert-butyl or t-butyl
C6H5- phenyl
-COOH Carboxylic acids Carboxy-
-COOR Ester Alkoxycarbony-
-COX (X=F, Cl, Br, I) Acyl halides Haloformyl-
-CONH2 Acid amide Carbamoyl-
-CN Nitriles Cyano-
-CHO Aldehyde Formyl-
>C=O Ketones Keto-/ oxo-
-OH Alcohol Hydroxy-
-NH2 Amine Amino-
-SH thiol Marcapto-
-Cl chloride Chloro-
-Br bromide Bromide-
-F fluoride Fluoro-
-I iodide Iodo-
 Rule of nomenclature
1. Find the longest carbon chain and add the suffix

Note that it does not matter if the chain is straight or it bends.

Also note that if there are two chains of equal length, pick the chain with more substituents.
In the following example, two different chains in the same alkane have seven C atoms. We
circle the longest continuous chain as shown in the diagram on the left, since this results in
the greater number of substituents.
2. Number the atoms in the carbon chain to give the first substituent the lowest number.
If the first substituent is the same distance from both ends, number the chain to give the
second substituent the lower number.
3. When numbering a carbon chain results in the same numbers from either end of the
chain, assign the lower number alphabetically to the first substituent.
If there are multiple functional group present in the molecules, then the carbon functional
group will be suffix and the others will be prefix
Nomenclature of different functional group

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 Ortho/peri fused aromatic system
1. The polycyclic system is oriented so that (a) the greatest number of rings are in a horizontal
row and (b) a maximum number of rings are above and to the right of the horizontal row
(upper right quadrant). If two or more orientations meet these requirements, the one is chosen
which has as few rings as possible in the lower left quadrant.

2. The system thus oriented is numbered in a clockwise direction commencing with the carbon
atom not engaged in ring-fusion in the most counter-clockwise position of the uppermost ring, or if
there is a choice, of the uppermost ring farthest to the right, and omitting atoms common to two or
more rings.

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Numbering

correct incorrect
1-Methylnaphthalene Anthracene

Phenanthrene

Steroids
Atoms common to two or more rings are designated by adding roman letters "a", "b", "c", etc.,
to the number of the position immediately preceding. Interior atoms follow the highest number,
taking clockwise sequence wherever there is a choice.

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 Cyclic system

Rule 1: Count the number of C's in the ring. If greater than or equal to the largest
substituent chain, the ring is the parent. If a substituent is larger, that is the parent.

Rule 2: for multi-substituted rings - start numbering at a point of attachment - number in

the direction that gives the lowest numbers. Substituents are numbered according to their
alphabetical priority - halogens included.
 Bicyclic system

1. Find highest group (suffix)

2. Count total carbon -decane
(10 carbon)

3. Identify no of ring and

bridgehead position (here 2, so bicyclo)

First Blue path

4. Numbering: start from
Second red path
bridgehead and follow the longest
Third green path
path, then 2nd longest, then 3rd
longest
Bridge length
5. Find all unique path between two 4 carbon
bridgeheadand count the no of carbon 3 carbon
and arrange them in descending order, 1 carbon
like [4.3.1] here

Put all together ==> bicyclo[4.3.1]decane

 Bicyclic system

Bicyclo[2.2.1]heptane Bicyclo[2.1.1]hexane

Bicyclo[4.4.0]decane
2-Bromo-8-chloro bicyclo[4.3.0]nonane

• Br on endo face away

from C-8.
6-endo-bromo-8-anti-isobutyl-1,3-
exo-dimethylbicyclo[3.2.1]octane
 Spiro System

• Since both bridgehead position are in same carbon, can not call bicyclo, call
“spiro” instead
• Nomenclature same as before

Spiro[5.4]decane

Spiro[4.3]octane

Spiro[6.3]octane
 Polyclic Systems

• Systematic name is adamantane.

• The largest ring and its main linkage forms bicyclic system.
• The location of 4th or secondary linkage shown by superscript

Tricyclo[3.3.1.13,7]decane

Tricyclo[3.2.1.02,4]octane not Tricyclo[4.1.0.12,5]octane

• One-atom bridge larger than no-atom bridge

• Main ring selected so as to include more atoms
• Main bridge should have more atoms

Tricyclo[2.2.1.02,6]heptane
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