Nomenclature of organic compounds

Nomenclature means the assignment of names to organic compounds. There are two main systems of nomenclature of
organic compounds.
(1) Trivial system : This is the oldest system of naming organic compounds. The trivial name was generally based on the
source, some property or some other reason. Quite frequently, the names chosen had Latin or Greek roots. For example,
(i) Acetic acid derives its name from vinegar of which it is the chief constituent (Latin : acetum = vinegar).
(ii) Formic acid was named as it was obtained from red ants. The Greek word for the red ants is formicus.
(iii) The names oxalic acid (oxalus), malic acid (pyrus malus), citric acid (citrus) have been derived from botanical sources
given in parentheses.
(iv) Urea and uric acid have derived their names from urine in which both are present.
(v) The liquid obtained by the destructive distillation of wood was named as wood spirit. Later on, it was named methyl
alcohol (Greek : methu = spirit; hule = wood).
(vi) Names like glucose (sweet), pentane (five), hexane (six), etc. were derived from Greek words describing their
properties or structures.
(vii) Methane was named as marsh gas because it was produced in marshes. It was also named as fire damp as it
formed explosive mixture with air.

Common or trivial names of some organic compounds.
Compound Common
name
Compound Common
name
Compound Common
name
Compound Common
name
CH
4
Methane CHCl
3
Chloroform (H
3
C)
2
CO Acetone C
6
H
5
NH
2
Aniline
C
2
H
2
Acetylene CHI
3
Iodoform CH
3
CH
2
OH Ethyl alcohol C
6
H
5
OH Phenol
H
3
CCH
2
CH
2
CH
3
n-Butane CH
3
CN Acetonitrile CH
3
CONH
2
Acetamide C
6
H
5
OCH
3
Anisole
(H
3
C)
2
CHCH
3
Isobutane CH
3
COOH Acetic acid CH
3
OCH
3
Dimethyl ether C
6
H
5
COCH
3
Acetophenone
(H
3
C)
4
C Neopentane C
6
H
6
Benzene (CH
3
CH
2
)
2
O Diethyl ether C
6
H
5
CONH
2
Benzamide
HCHO Formaldehyde C
6
H
5
CH
3
Toluene

(2) IUPAC system : In order to rationalise the system of naming, an International Congress of Chemists was held in Geneva in
1892. They adopted certain uniform rules for naming the compounds.
The system of nomenclature was named as Geneva system. Since then the system of naming has been improved from
time to time by the International Union of Pure and Applied Chemistry and the new system is called IUPAC system of naming.
This system of nomenclature was first introduced in 1947 and was modified from time to time. The most exhaustic rules for
nomenclature were first published in 1979 and later revised and updated in 1993. The rules discussed in the present chapter are
based on guide books published by IUPAC in 1979 (Nomenclature of Organic Chemistry by J. Rigandy and S.P. Klesney) and 1993
(A Guide to IUPAC Nomenclature for Organic Chemistry by R. Panico, W.H. Powell and J.C. Richer). With the help of this system,
an organic compound having any number of carbon atoms can be easily named.
IUPAC System of Naming Organic Compounds : In the IUPAC system, the name of an organic compound consist of
three parts : (i) Word root (ii) Suffix (iii) Prefix
(i) Word root : The word root denotes the number of carbon atoms present in the chain.

Chain
length
Word root Chain
length
Word root Chain
length
Word
root
Chain
length
Word
root
C
1
Meth- C
6
Hex- C
11
Undec- C
16
Hexadec-
C
2
Eth- C
7
Hept- C
12
Dodec- C
17
Heptadec-
C
3
Prop- C
8
Oct- C
13
Tridec- C
18
Octadec-
C
4
But- C
9
Non- C
14
Tetradec- C
19
Nonadec-
C
5
Pent- C
10
Dec- C
15
Pentadec- C
20
Eicos

(ii) Suffix : The word root is linked to the suffix which may be primary or secondary or both.
(a) Primary suffix : A primary suffix is added to the word root to indicate whether the carbon chain is saturated or
unsaturated.

Type of carbon
chain
Primary suffix General name
Saturated (C C) ane Alkane
Unsaturated (C = C) ene Alkene
Unsaturated (C C) yne Alkyne
If the parent chain contains two, three or more double or triple bonds, then the numerical prefixes such as di (for two),
tri (for three), tetra (for four), etc. are added to the primary suffix.
(b) Secondary suffix : A secondary suffix is then added to the word root after the primary suffix to indicate the
functional group present in the organic compound.


Class of org.
compound
Functional group Secondary
suffix
Class of org.
compound
Functional
group
Secondary
suffix
Alcohols OH ol Acid chlorides COCl oyl chloride
Aldehydes CHO al Acid amides CONH
2
amide
Ketones > C = O one Nitriles C

N nitrile
Carboxylic acids COOH oic acid Amines NH
2
amine
Esters COOR alkyl.... oate Thiol SH thiol

It may be noted that while adding the secondary suffix to the primary suffix, the terminal 'e' of the primary suffix (i.e.
ane, ene and yne) is droped if the secondary suffix begins with a vowel but is retained if the secondary suffix begins with a
consonant. For example
Organic compound CH
3
CH
2
OH CH
3
CH
2
CN
Word root Eth Prop
Primary suffix an (e)* ane
Secondary suffix ol nitrile
IUPAC name Ethanol Propanenitrile

The terminal 'e' from the primary suffix has been dropped because the secondary suffix i.e. 'ol' begins with a vowel 'o'.
(iii) Prefix : There are many groups which are not regarded as functional groups in the IUPAC name of the compound.
These are regarded as substituents or side chains. These are represented as prefixes and are placed before the word root while
naming a particular compound. These may be :
(a) Alkyl groups : These groups contain one hydrogen atom less than the alkane. These are named by substituting the
suffix ane of the name of the corresponding alkane by yl. i.e. alkane ane + yl = alkyl.
For example,

4
CH
: Methane becomes

3
CH
: Methyl

3 3
CH CH
: Ethane becomes

2 3
CH CH
: Ethyl
3 2 3
CH CH CH
: Propane becomes

2 2 3
CH CH CH
: Propyl etc.
(b) Functional groups not regarded as principal functional groups : If a compound contains more than one functional
group, then one of the functional group is regarded as principal functional group and other is treated as secondary suffix. The
other functional groups are regarded as substituent and are indicated by prefixes.
Substituent Prefix Substituent Prefix
F Fluoro OCH
3
Methoxy
Cl Chloro OC
2
H
5
Ethoxy
Br Bromo NO
2
Nitro
I Iodo NH
2
Amino
NO Nitroso OH Hydroxy
N = N Diazo

Thus, a complete IUPAC name of an organic compound may be represented as:
Prefix + word root + Primary suffix + Secondary suffix





Word root : Pent (five C C C C C) Primary suffix : ene (double bond at C 2)
Secondary suffix : oic acid ( COOH group) Prifix : Bromo ( Br group at C 4)
IUPAC name : Bromo + pent + ene + oic acid or 4-Bromopent -2-en-1-oic acid
Classification of carbon atoms in organic compounds
The carbon atoms in an alkane molecule may be classified into four types as primary (1
o
), secondary (2
o
), tertiary (3
o
)
and quaternary (4
o
). The carbon atoms in an organic compound containing functional group can be designated as , , , .

3
1
|
3
1 3
3
1
3
1
|
|
4
2
2
3
1
CH
CH CH
CH
CH
C CH CH
o
o o
o
o
o o o


Alkyl groups
Functional group
3 2 2 2
CH CH CH CH OH


3 2 2
|
3
CH CH CH CH CHO
CH


Prefix
Pri. suffix
OH
O
C CH CH
Br
CH CH =
|| 1 2 3
|
4 5
3

Sec. suffix

These are univalent groups or radicals obtained by the removal of one hydrogen atom from a molecule of a paraffin.
The symbol 'R' is often used to represent an alkyl group.

) ( ) (
group) (Alkyl (Alkane)
1 2 2 2


+

+
R H R
H C H C
n n
H
n n

Alkyl groups are named by dropping-ane from the name of corresponding paraffin and adding the endingyl.
Parent saturated hydrocarbon Name of the alkyl group Structure
Methane Methyl CH
3

Ethane Ethyl CH
3
CH
2

Propane n-Propyl CH
3
CH
2
CH
2

Butane n-Butyl CH
3
CH
2
CH
2
CH
2

Alkyl groups derived from saturated hydrocarbons having three or more carbon atoms exist in isomeric forms.


Similarly, removal of different H atoms in pentane gives the following radicals :

3 2 2 2 2
n Pentyl
CH CH CH CH CH

;
3 2 2
3
CH CHCH CH
|
CH Isopentyl
;
3
3 2
3
Neopentyl
CH
|
CH C CH
|
CH

;
3 2 2 3
sec Pentyl
CH CHCH CH CH
|

;
3
3 2 3
tert Pentyl
CH
|
CH CCH CH
|

Table : Unsaturated groups or radicals
Group Common name IUPAC name
= CH CH
2

Vinyl Ethenyl
=
2
1 2
2
H C H C CH

Allyl 2-Propenyl
= H C CH CH
1
3

1-Propenyl
C HC

Acetylide Ethynyl

1
2
2
CH C HC

Propargyl 2-Propynyl

General rules for naming organic compounds
In the common system, all the isomeric alkanes (having same molecular formula) have the same parent name. The
names of various isomers are distinguished by prefixes. The prefix indicates the type of branching in the molecule. For example,
(1) Prefix n-(normal) is used for those alkanes in which all the carbon atoms form a continuous chain with no branching.

Butane
3 2 2 3
n
CH CH CH CH
;
Pentane
3 2 2 2 3
n
CH CH CH CH CH

(2) Prefix iso is used for those alkanes in which one methyl group is attached to the next-to-end carbon atom (second last) of the
continuous chain.

3 3
|
3
Isobutane
CH CHCH
CH

3 2 3
|
3
Isopentane
CH CH CH CH
CH

3 2 2 3
|
3
Isohexane
CH CHCH CH CH
CH

(3) Prefix neo is used for those alkanes which have two methyl groups attached to the second last carbon atom of the
continuous chain.

3
|
3 3
|
3
Neopentane
CH
CH C CH
CH

3
|
3 2 3
|
3
Neohexane
CH
CH C CH CH
CH


IUPAC system of nomenclature of complex compounds
The naming of any organic compound depends on the name of normal parent hydrocarbon from which it has been
derived. IUPAC system has framed a set of rules for various types
of organic compounds.
(1) Rules for Naming complex aliphatic compounds when no
functional group is present (saturated hydrocarbon or paraffins
or Alkanes)
Butane
3 2 2 3
n
CH CH CH CH

Butyl
2 2 2 3
n CH CH CH CH

Butyl . sec CH

3
2 3
CH
CH CH

Substituents
Substituents
Parent chain
3
|
3 2 2 2 3
| |
3 3
CH
CH CH CH CH C CH CH
CH CH


(i) Longest chain rule : The first step in naming an organic compound is to select the longest continuous chain of carbon
atoms which may or may not be horizontal (straight). This continuous chain is called parent chain or main chain and other
carbon chains attached to it are known as side chains (substituents). Examples :
If two different chains of equal length are possible, the chain with maximum number of side chains or alkyl groups is selected.
(ii) Position of the substituent : Number of the carbon atoms in the parent chain as 1, 2, 3,....... etc. starting from the
end which gives lower number to the carbon atoms carrying the substituents. For examples,

(Correct) A
1 | 2 3 4 5
C C C C C
X


(Wrong) B
5 | 4 3 2 1
C C C C C
X


The number that indicates the position of the substituent or side chain is called locant.

ane Methylpent 2
3
|
3
1 2
2
3
2
4
3
5

CH
H C H C H C H C H C

e Ethylhexan 3
3 2 2
6 5 | 4
3
3
2
2
3
1

CH CH CH
H C H C H C H C H C

(iii) Lowest set of locants : When two or more substituents are present, then end of the parent chain which gives the
lowest set of the locants is preferred for numbering.
This rule is called lowest set of locants. This means that when two or more different sets of locants are possible, that
set of locants which when compared term by term with other sets, each in order of increasing magnitude, has the lowest term
at the first point of difference. This rule is used irrespective of the nature of the substituent. For example,

(Correct) 5 3, 2, : locants of Set
3
|
3
1 2
3
|
3
2
4
3
|
5 6
3
CH
H C H C
CH
H C H C
CH
H C C H

(Wrong) 5 4, 2, : locants of Set
3
|
3
6 5
3
|
4
2
3
3
|
2 1
3
CH
H C H C
CH
H C H C
CH
H C C H

The correct set of locants is 2, 3, 5 and not 2, 4, 5. The first set is lower than the second set because at the first
difference 3 is less than 4. (Note that first locant is same in both sets 2; 2 and the first difference is with the second locant 3, 4.
We can compare term by term as 2-2, 3-4 (first difference), 5-5. Only first point of difference is considered for preference.
Similarly for the compounds,
3
|
3
1 2
2
3
3
|
2
4
2
5
2
6 7
3
|
8
2
9
3
10
CH
H C H C H C
CH
H C H C H C H C
CH
H C H C H C
3
|
3
10 9
2
8
3
|
2
7
2
6
2
5 4
3
|
3
2
2
3
1
CH
H C H C H C
CH
H C H C H C H C
CH
H C H C H C

Set of locants : 2, 7, 8 (Correct) Set of locants : 3, 4, 9 (Wrong)
First set of locants 2, 7, 8 is lower than second set 3, 4, 9 because at the first point of difference 2 is lower than 3.

Lowest sum rule : It may be noted that earlier, the numbering of the parent chain containing two or more substituents
was done in such a way that sum of the locants is the lowest. This rule is called lowest sum rule. For example, the carbon chain
of alkanes given below should be numbered as indicated in structures A and not according to structure B.

3 2
3 2
1 | 2
7
3 2
6
2
5 | 4 3
3
CH CH
CH CH
CH H C H C H C H C CH

;
3 2
3 2
7 6 |
1
3 2
2
2
3 | 4 5
3
CH CH
CH CH
CH H C H C H C H C CH

A (correct) Sum of locants =3+4=7 B (wrong) Sum of locants =4+5=9
According to latest IUPAC system of nomenclature, the lowest set of locants is preferred even if it violates the lowest
sum rule. For example,

This compound is numbered as 2, 7, 8 and not as 3, 4, 9 in accordance with latest lowest set of locants rule, even
though it violates lowest sum rule.
(iv) Presence of more than one same substituent : If the same substituent or side chain occurs more than once, the
prefixes di, tri, tetra ..........etc., are attached to the names of the substituents. For example,

entane Trimethylp - 4 2, 2,
3
3
|
3
1 2 |
3
|
2
3 4
3
5
CH
CH
H C C
CH
H C H C H C

(v) Naming different substituents : If two or more different substituents or side chains are present in the molecule,
they are named in the alphabetical order along with their appropriate positions.
Set of locants = 3, 4, 9

(Wrong)
1 2 3 4 5 6 7 8 9 10
3 2 2 2 2 2 3
| | |
3 3 3
CH CH CH CH CH CH CH CH CH CH
CH CH CH
Structure (B)

Set of locants = 2, 7, 8

(Correct)
10 9 8 7 6 5 4 3 2 1
3 2 2 2 2 2 3
| | |
3 3 3
CH CH CH CH CH CH CH CH CH CH
CH CH CH
Structure (A)


2 3
3| 5 4 2 1
3 2 3
| |
3 3
3-Ethyl-2, 3-dimethylpentane
CH CH
CH CH C CH CH
CH CH


3 3
2| 3| 1
3 2 3
|
3
2
6
2 3
4 |
5 |
3-Ethyl-2, 2, 3-trimethylhexane
CH CH
CH C C CH CH
CH
CH
CH CH

(vi) Naming different substituents at equivalent position : In case, there are different alkyl substituents at equivalent
positions, then numbering of the parent chain is done in such a way that the alkyl group which comes first in the alphabetical
order gets the lower number.
hexane methyl - 4 - Ethyl - 3
5 2
|
3
1
2
2 3
3
|
4
2
5
3
6
H C
H C H C H C
CH
H C H C H C

hexane dimethyl - 4 4, - Diethyl - 3 3,
3
3
|
3
6
2
5 | 4
5 2
5 2
|
| 3
2
2
3
1
CH
CH
H C H C C
H C
H C
C H C H C

(vii) Naming the complex substituents (or substituted substituents) : If the substituent on the parent chain is complex
(i.e. it is branched) it is named as substituted alkyl group by numbering the carbon atom of this group attached to the parent
chain as 1. The name of such substituent is given in brackets in order to avoid confusion with the numbering of the parent chain.
For example,
3
| 3
3
| 2
3
| 1
3
9
2
8
2
7
2
6 5
2
4
2
3
2
2
3
1
CH
CH CH
CH CH
H C H C H C H C H C H C H C H C H C

The name of the complex substituent is always written in brackets.
While deciding the alphabetical order of the various substituents, the name of the complex substituent is considered to
begin with the first letter of the complete name. It may be remembered that in case of simple substituents, however, the
multiplying prefixes are not considered. The names of simple substituents are first alphabetized and then multiplying prefixes
are inserted. For example,

It may be noted that dimethyl propyl (a complex substituent) is alphabetized under d and not under m. Therefore, it is
cited before ethyl (e).

The substituent dimethyl is cited first because it is alphabetized under d. Similarly,

Complex substituent
( 1, 1-dimethylpropyl)
Complex substituent
( 2-methylpropyl)
3
|1 2 3
3 2 3
|5 9 8 7 6 4 3 2 1
3 2 2 2 2 2 2 3
|1 2 3
2 3
|
3
CH
CH C CH CH
CH CH CH CH C CH CH CH CH
CH CH CH
CH



5-(1, 1-Dimethylpropyl) 5-(2-methylpropyl) nonane
Complex substituent
(1, 2-dimethylpropyl)
5-(1, 2-Dimethylpropyl)-7-ethyl undecane
2 3
|7 1 2 3 4 5 6 8 9 10 11
3 2 2 2 2 2 2 2 3
1
3
2
3
3
3
CH -CH
CH -CH -CH -CH -CH-CH - CH-CH -CH -CH -CH
|
CH CH
|
CH CH
|
CH

Complex substituent
5-(1, 2-Dimethylpropyl) nonane



5(1-methyl butyl)-7-(2-methyl butyl) dodecane
When the names of two or more complex substituents are composed of identical words, priority for citation is given to
the substituent which has lowest locant at the first cited point of difference within the complex substituent. For example,
The substituent (1-methylbutyl) is written first because it has lower locant than the substituent (2-methylbutyl).
When the same complex substituent (substituted in the same way) occurs more than once, it is indicated by the
multiplying prefix bis (for two), tris (for three), tetra kis (for four) etc.


(viii) Cyclic hydrocarbons : These compounds contain carbon chain skeletons which are closed to form rings. The saturated
hydrocarbons with ring of carbon atoms in the molecule are called cycloalkanes. These have the general formula
n n
H C
2
.
The cyclic compound is named by prefixing cyclo to the name of the corresponding straight chain alkane. For example,


If side chains are present, then the rules given in the previous section are applied. For example,

When more than one side chains are present, the numbering is done beginning with one side chain so that the next
side chain gets the lower possible number. For example,

When a single ring system is attached to a single chain with a greater number of carbon atoms or when more than one ring
system is attached to a single chain, then it is named as cycloalkylalkanes. For example,
CH
2
CH
3

2
3
CH
3
CH
3

1
3-Ethyl-1, 1-dimethylcyclohexane

CH
2
CH
2
CH
3
6 2
3
4
5
CH
3

1-Methyl-3-propylcyclohexane

1
CH
3

CH
3

1.3-Dimethylcyclobutane
1 2
3 4
CH
3

Methylcyclohexane
C
2
H
5

Ethylcyclopentane
C
6
H
12
, Cyclohexane C
5
H
10
, Cyclopentane C
3
H
6
, Cyclopropane
C
4
H
8
, Cyclobutane
5, 5-Bis (1, 1-dimethylpropyl)-2-methyldecane
1,1 dimethylpropyl
1,1 dimethylpropyl
|5 10 9 8 7 6 4 3 2 1
3 2 2 2 2 2 2 3
|
3
CH CH CH CH CH C CH CH CH CH
CH

3
3
1 |
2
2
3
3
CH
CH C H C H C
3
|
3
| 1
2
2
3
3
CH
H C C H C H C
2-methylbutyl
3
|
3
4
2
3 2
2
1 |
CH
H C H C H C H C

3
4
2
3
2
2
3
1 |
H C H C H C
CH
H C
1-methylbutyl
|5 12 11 10 9 8 7 6 4 3 2 1
C H C H C H C H C H C H C H C H C H C H C H C H
3 2 2 2 2 2 2 2 2 3

Complex substituent
( 1, 1-dimethylpropyl)
4-(1, 1-Dimethylpropyl) 3-ethyl-4, 7-dimethyldecane
2 5 3 3
3| 4| |7 1 2 5 6 8 9 10
3 2 2 2 2 2 3
C H CH CH
CH CH CH C CH CH CH CH CH CH
3
3
2 |
1 |
3
CH
CH
C C H



In case of substituted cycloalkenes, the double bond is given the lowest possible number and numbering is done in such
a way that the substituents get the lowest number.






According to the IUPAC system of Nomenclature, certain trivial or semi- systematic names may be used for
unsubstituted radicals. For example, the following names may be used,

According to the IUPAC system of Nomenclature, certain trivial or semi- systematic names may be used for
unsubstituted radicals. For example, the following names may be used,
CH CH
2 3
) (

Isopropyl
2 2 3
) ( CH CH CH

Isobutyl

3
|
2 3
CH
CH CH CH

Sec- Butyl C CH
3 3
) (

tert-Butyl

2 2 2 3
) ( CH CH CH CH

Isopentyl
2 3 3
) ( CH C CH

Neopentyl
3
3
|
|
2 3
CH
CH
C CH CH

tert-Pentyl CH CH CH CH CH
2 2 2 3
) (

Isohexyl

However, when these are substituted, these names cannot be used as such. For example,

3
|
2
ne methylocta 4 isopropyl 5 Diethyl 3 , 3
3 2
|
3
1
2
2 3 |
3
|
4
3
|
3
|
5
2
6
2
7
3
8
CH
CH
CH CH
H C H C C
CH
H C
CH
CH CH
H C H C H C H C

It may be noted that while writing the substituent's name in alphabetical order, the prefixes iso-and neo-are considered
to be part of the fundamental name. However, the prefixes sec-and tert-are not considered to be the part of the fundamental
name.
(2) Rules for IUPAC names of polyfunctional organic compounds
Organic compounds which contain two or more functional groups are called polyfunctional compounds. Their IUPAC
names are obtained as follows,
(i) Principal functional group : If the organic compound contains two or more functional groups, one of the functional
groups is selected as the principal functional group while all the remaining functional groups (also called the secondary
functional groups) are treated as substituents. The following order of preference is used while selecting the principal functional
group.
Sulphonic acids > carboxylic acids > anhydrides > esters > acid chlorides > acid amides > nitriles > aldehydes > ketones >
thiols > alcohols >alkenes > alkynes.
All the remaining functional groups such as halo (fluoro, chloro, bromo, iodo), nitroso (NO), nitro (NO
2
), amino (
NH
2
) and alkoxy (OR) are treated as substituents.
Table : 22.12
Order of
preference
Preflx Suffix (ending) Order of
preference
Preflx Suffix (ending)
1 SO
3
H Sulpho Sulphonic acid 9 OH Hydroxy ol
2 COOH Carboxy oic acid 10 NH
2
Amine amine
3 COOR Alkoxy carbonyl Alkyl alkanoate 11 C = C ene
4 COX Haloformyl Oyl halide 12 C C yne
Cyclohexyl cyclohexane

2 2 2
CH CH CH

CH
3

CH
3

1, 3-Bis (2-methylcyclopropyl)
propane
3 2 2 2 2
CH CH CH CH CH
1-Cyclobutylpentane
3
4
2
3
2
2
2
1
H C H C H C H C
1-Cyclopropyl butane
CH
3

CH
3

3
2
1
2, 3-Dimethylcyclopent-1ene
CH
3

2
1
3-Methylcyclohex-1-ene

5 CONH
2
Carbamoyl amide 13 O Epoxy
6 C N Cyano nitrile 14 X Halo
7 CHO Formyl al 15 NO
2
Nitro
8 > C = O Keto one
(ii) Selecting the principal chain : Select the longest continuous chain of carbon atoms containing the principal
functional group and maximum number of secondary functional groups and multiple bonds, if any.
(iii) Numbering the principal chain : Number the principal chain in such a way that the principal functional group gets
the lowest possible number followed by double bond and triple bond and the substituents, i.e.
Principal functional group > double bond > triple bond > substituents
(iv) Alphabetical order : Identify the prefixes and the positional numbers (also called locants) for the secondary
functional groups and other substituents and place them in alphabetical order before the word root.

(3) Polyfunctional compounds containing more than two like functional groups : According to latest convention (1993
recommendations for IUPAC nomenclature), if an unbranched carbon chain is directly linked to more than two like functional
groups, the organic compound is named as a derivative of the parent alkane which does not include carbon atoms of the
functional groups. For example,

dinitrile) 1,5 ne, cyanopenta 3 (Formerly
trile tricarboni - -1,2,3 Propane
2
1
2
2
3
|
CN
CN H C H C H C NC

acid) dioic - 1,7 - tane carboxyhep - 4 (Formerly
acid lic tricarboxy - 1,3,5 - Pentance
2
1
2
2
3
2
4
2
5
|
COOH
COOH H C H C H C H C H C HOOC


Following the above rule, citric acid may be named as,

OH
COOH
COOH H C C H C HOOC
|
|
2
3
2
2
1


2-Hydroxypropane-1, 2, 3-tricarboxylic acid (formerly 3-carboxy-3-hydroxypentane-1, 5-dioic acid )

Bond-line Notation of organic compounds
Sometimes, the bonds between carbon atoms are represented by lines. For example, n-hexane has a continuous chain
of six carbon atoms which may be represented as,

CH CH
2 3
) (

Isopropyl
2 2 3
) ( CH CH CH

Isobutyl
3
|
2 3
CH
CH CH CH

Sec- Butyl C CH
3 3
) (

tert-Butyl

2 2 2 3
) ( CH CH CH CH

Isopentyl
2 3 3
) ( CH C CH

Neopentyl
3
3
|
|
2 3
CH
CH
C CH CH

tert-Pentyl C CH CH CH CH
2 2 2 3
) (

Isohexyl

However, when these are substituted, these names cannot be used as such. For example,

3
|
2
ne methylocta 4 isopropyl 5 Diethyl 3 , 3
3 2
|
3
1
2
2 3 |
3
|
4
3
|
3
|
5
2
6
2
7
3
8
CH
CH
CH CH
H C H C C
CH
H C
CH
CH CH
H C H C H C H C

It may be noted that while writing the substituent's name in alphabetical order, the prefixes iso-and neo-are
considered to be part of the fundamental name. However, the prefixes sec-and tert-are not considered to be the part of
the fundamental name.

Bond-line Notation of organic compounds
Principal functional
group
Substituent
4-Hydroxy pentanoic acid
OOH C
1

4| 5 3 2
3 2 2
CH CH CH CH
OH

Sometimes, the bonds between carbon atoms are represented by lines. For example, n-hexane has a continuous
chain of six carbon atoms which may be represented as,

Hexane
3 2 2 2 2 3

n
CH CH CH CH CH CH

In this notation, the carbon atoms are represented by line ends and intersections. It is assumed that the required
number of hydrogen atoms are present wherever they are necessary to satisfy the tetravalency of carbon. A single line
represents a single bond (C C), two parallel lines represent a double bond (C = C) and three parallel lines represent a
triple bond
) ( C C
. For example,



Nomenclature of Bicyclic compounds
Many hydrocarbons and their derivatives contain two fused or bridged rings. The carbon atoms common to both
rings are called bridge head atoms and each bond or chain of carbon atoms connecting both the bridge head atoms is
called as bridge. The bridge may contain 0, 1, 2.... etc. carbon atoms. For example,

These bicyclic compounds are named by attaching the prefix 'bicyclo' to the name of the hydrocarbon having the
same total number of carbon atoms as in the two rings. The number of carbon atoms in each of the three bridges
connecting the two bridge head carbon atoms is indicated by arabic numerals, i.e., 0, 1, 2.....etc. These arabic numerals
are arranged in descending order; separated from one another by full stops and then enclosed in square brackets. The
complete IUPAC name of the hydrocarbon is then obtained by placing these square brackets containing the arabic
numerals between the prefix bicyclo and the name of alkane. For example,

If a substituent is present, the bicyclic ring system is numbered. The numbering begins with one of the bridge
head atoms, proceeds first along the longest bridge to the second bridge head atom, continues along the next longest
bridge to the first bridge head atom and is finally completed along the shortest path. For example,
Bicyclo [2, 2, 2] octane Bicyclo [4, 4, 0] decane

Bicyclo [1, 1, 0] butane

Bicyclo [3, 1, 1] heptane
Bicyclo [2, 2, 1] heptane

One carbon bridge
CH
CH
CH
2
Bridge head atom
Bridge head atom
Two
carbon
bridge
Two
carbon
bridge
2
2
CH
|
CH

2
2
CH
|
CH

One carbon bridge

CH
CH
CH
2
CH
2
Bridge head atom
Zero carbon bridge
One carbon
bridge
Bridge head atom
2
3
4
5
6
OH
3, 3, 5-trimethylhex-1-en-2-ol
8
5
6
2
3
4
O
5, 6-Dimethylcyclohex-2-en-1-one
2
3
4
5
1
3-Ethyl penta-1, 3-diene
2
1
4
5
3
OH
4-Hydroxy-4-methyl pentan-2-one
1
3
2
1, 3-Dimethyl cyclohex-1-ene
OH
3
2
1
3-Cyclohexyl butan-2-ol
2
3
1
3-Methyl cyclohex-1-ene
1-Methyl-3-propylcyclohexane
1
2
3
3-Ethyl-1, 1-dimethylcyclohexane



Nomenclature of spiro compounds
Compounds in which one carbon atom is common to two different rings are called spi ro compounds. The
IUPAC name for a spiro compound begins with the word spiro followed by square brackets containing the number of
carbon atoms, in ascending order, in each ring connected to the common carbon atom and then by the name of the
parent hydrocarbon corresponding to the total number of the carbon atoms in the two rings. The position of
substituents are indicated by numbers ; the numbering beginning with the carbon atom adjacent to the spiro carbon
and proceeding first around the smaller ring and then to the spiro atom and finally around the larger ring For
example,





Nomenclature of special compounds

Unbranched assemblies consisting of two or more
identical hydrocarbon units joined by a single bond are
named by placing a suitable numerical prefix such as bi for
two, ter for three, quater for four, quinque for five etc. before
the name of the repititive hydrocarbon unit. Starting from
either end, the carbon atoms of each repititive hydrocarbon
unit are numbered with unprimed and primed arabic
numerals such as 1, 2, 3...., 1', 2', 3' ....., 1'', 2'', 3''..... etc. The
points of attachment of the repititive hydrocarbon units are
indicated by placing the appropriate locants before the name. For example,

As an exception, unbranched assemblies consisting of benzene rings are
named by using appropriate prefix with the name phenyl instead of benzene.
For example,

If two atoms/groups of same preference occupy identical
positions from either end of the parent chain, the lower number
must be given to the atom/group whose prefix comes first in the
alphabetical order. For example,

When two or more prefixes consist of identical words, the priority for
citation is given to that group which contains the lowest locant at the first point
of difference. For example,
If a compound contains a benzene ring coupled to an alicyclic ring, it is named
as a derivative of benzene, i.e. compound having lowest state of hydrogenation.
For example,

In the common system of nomenclature, prefixes iso and neo are used only for compounds containing an isopropyl
group,
CH CH
2 3
) (
and a tert-butyl group,
C CH
3 3
) (
respectively at the end of the carbon chain.
Nomenclature of simple aromatic compounds
5
1
2
3
4
6
7
Spiro [2.4] heptane
2-Chlorospiro [3.5] decane
1
2
3
4 5 6
7
8 9

10
2, 6, 6-Trimethylbicyclo [3, 1, 1] hept-2-ene
1
2
3
7
4
5
6
6
2
3
4
5
1
7
8
9
CH
3
8-Methylbicyclo [4, 3, 0] nonane 8-Chlorobicyclo [3, 2, 1] octane
1
2
3
4
5
8 7
Cl
6
3
1 1'
2
3
2'
3'
1, 1' -Bicyclopropane
1 2
3 4
1'

2'

3'

4'

1' 2'
4' 3'
1, 1', 2', 1'' -Tercyclobutane
1
2

3

4

5

6

1'
2'

3'

4'

5'

6'

1'

2'

3'

5'

4'

6'

1, 1', 4', 1'' -Terphenyl
4 3 2 1
2 2 2 2
1-Bromo-4-chlorobutane
Cl CH CH CH CH Br
5 4 3 2 1
3 3
||
| |
3 2 3
2 ethoxy-4-methoxy pentan-3-one
CH CH C CH CH
O
OCH OCH CH

1
2

3
4

Cl
2

1
Cl
1-(2-chlorolphenyl)-2-(4-chlorophenyl) ethane
1 2
2 2
CH CH

Aromatic compounds are those which contain one or more benzene rings in them. An aromatic compound has
two main parts : (1) Nucleus, (2) Side chain
(1) Nucleus :The benzene ring represented by regular hexagon of six carbon atoms with three double bonds in
the alternate positions is referred to as nucleus. The ring may be represented by any of the following ways,





(i) (ii) (iii) (iv)
(2) Side chain : The alkyl or any other aliphatic group containing at least one carbon atom attached to the
nucleus is called side chain. These are formed by replacing one or more hydrogen atoms in the ring by alkyl radicals
i.e., R (R may be
3
CH
,
5 2
H C
,
7 3
H C
etc.)




If one atom of hydrogen of benzene molecule is replaced by another atom or group of atoms, the derivative
formed is called monovalent substituted derivative. It can exist only in one form because all the six hydrogens of
benzene represent equivalent positions. For example,
X H C
5 6
, where X is a monovalent group.
When two hydrogen atoms of benzene are replaced by two monovalent atoms or group of atoms, the resulting product disubstituted
benzene derivative can have three different forms. These forms are distinguished by giving the numbers. The position occupied by
the principle functional group is given as 1 and the other position is numbered in a clockwise direction which gvies lower locatant to
the substituents.
(i) Ortho (or 1, 2-) : The compound is said to be ortho (or 1, 2-) if the two substituents are on the adjacent carbon atoms.
(ii) Meta (or 1, 3-) : The compound is said to be meta or (1, 3-) if the two substituents are on alternate carbon atoms.
(iii) Para (or 1, 4-) : The compound is said to be para or (1, 4-) if the two substituents are on diagonally situated carbon
atoms.
Ortho, meta and para are generally represented as o-, m- and p- respectively as shown below,

Aryl group : The radicals obtained by removal of one or more hydrogen atoms of the aromatic hydrocarbon molecules are
known as aryl radicals or aryl groups. For example,

Nomenclature of different aromatic compounds : The names of few simple aromatic compounds are given below :
Hydrocarbons

The aromatic hydrocarbons may also contain two or more benzene rings condensed together.
CH
3

CH
3

1, 3-Dimethylbenzene
(m-Xylene)
CH
3

CH
3

1, 4-Dimethylbenzene
(p-Xylene)
H
3
C
CH
3

CH
3

1, 3, 5-Trimethyl
benzene (Mesitylene)
Benzene
CH
3

Toluene
CH
2
CH
3

Ethylbenzene
CH
3

CH
3

1, 2-Dimethyl benzene

Phenyl
(From nucleus)
CH
2

Benzyl
C
Benzo
CH

Benzal
From side chains
X
X
1
2
(1, 2-)

X
X
1
2
3
(1, 3-) Meta
X
X
1
2
3
4
(1, 4-) para
CH
CH
CH
CH
HC
HC
R Side chain
Ring or nucleus


Halogen derivatives Side chain substituted
Nuclear substituted








Hydroxy derivatives


Ethers Aldehydes and ketones (Nuclear substituted)



Carboxylic acids (Nuclear substituted)

Acid derivatives
Amino derivatives (Nuclear substituted) Sulphonic acids Nitro derivatives

OC
CO

O

Benzoic anhydride Phenyl benzoate
COOC
6
H
5
Ethyl 4-bromobenzoate
COOC
2
H
5
Br

Benzoyl chloride
C Cl

O

Benzamide
C NH
2
O

Methyl benzoate
COOCH
3
Ethyl benzoate
COOC
2
H
5
COOH

Phthalic acid
(1,2 benzene
dicarboxylic acid)
COOH

Isophthalic acid
(1,3 benzene
dicarboxylic acid)
COOH

COOH

Terephthalic acid
(1,4 benzene
dicarboxylic acid)
COOH

COOH

Benzoic acid
COOH

o-Toluic acid
CH
3
COOH

2-Hydroxy benzoic acid

COOH

OH

Benzaldehyde
CHO

Methyl phenyl ketone
(Acetophenone)
COCH
3
CO
Diphenyl ketone
(Benzophenone) or
diphenyl methanone
Methoxybenzene
(Anisole)
OCH
3
Ethoxybenzene
(Phenetole)
OCH
2
CH
3
O
Phenoxybenzene
1, 2-Dihydroxybenzene
(Catechol)
OH

OH
1, 3-Dihydroxybenzene
(Resorcinol)
OH

OH
1, 4-dihydroxy-
benzene (Quinol)
OH
OH
Phenol
OH
2-Methyl
phenol

CH
3
OH
Benzyl alcohol
CH
2
OH
Naphthalene
Anthracene Phenanthrene
Cl
Chlorobenzene
Cl
CH
3

2-Chlorotoluene
(o-Chlorotoluene)
Cl
Cl
1,2-Dichlorobenzene
(o-Dichlorobenzene)
CH
2
Cl
Phenyl chloromethane
(Benzyl chloride)
CHCl
2
Phenyl dichloromethane
(Benzal chloride)
CCl
3
Phenyl trichloromethane
(Benzo chloride)



Some tips for nomenclature of aromatic compounds : For IUPAC nomenclature of substituted benzene compounds,
the substituent is placed as prefix to the word benzene. It may be noted that common names of many substituted benzene
compounds are still universally used. Some important tips for nomenclature of organic compounds are given below,
(i) When the benzene ring is named as substituent on the other molecule, it is named as phenyl group. It is treated in the
nomenclature just like the name of an alkyl group. It is abbreviated as Ph. For example,
or Ph CHO CH CH
2 2
3-Phenylpropanal
acid enoic - 2 - Phenylprop - 3
1 2 3 |
Ph
OOH C H C H C =
ol - 2 - entan diphenyl p 3 3,
|
3
1 2
5 6
5
5
2
4
|
| 3
5 6
OH
H C H C
H C
H C
C H C
or Ph
3
4 3 2
2
1
H C C C H C Phenylbut-2-yne



(ii) Disubstituted, trisubstituted or tetrasubstituted benzenes are named by using the numbers for the positions of the substituents.


(iii) If different groups are attached to the benzene ring, then the following rules are kept in mind,
(a) The principal group is fixed as number 1.
(b) The numbering of the chain is done in any direction (clockwise or anticlockwise) which gives lower number to the
substituents.
(c) The substituents are written in alphabetical order. For example,

CHO
1
2
3
4
4-Methoxy benzaldehyde
OCH
3
COOH
1
2
3
NO
2

HO
4
5
2-Bromo-5-hydroxy-
3-nitrobenzoic acid
Br
6
NH
2
1
2
2, 3-Dimethyl aniline
CH
3
CH
3
3
5
6
1
2
NH
2

4-Aminobenzoic acid
(COOH is principal

COOH
3 OH
1
2
Cl
2-Chlorophenol
Cl
1
2
Cl
1, 2-Dichlorobenzene
NO
2

1
2
3
NO
2
NO
2

4
5
1, 3, 5-Trinitrobenzene
CH
3

1
2
3
CH
3

1, 3-Dimethyl benzene
OCH
3
1
2
3
4
2-Chloro-4-methyl anisole
Cl

CH
3
OH

1
2
3
4
3, 4-Dimethylphenol
CH
3
CH
3
CHO

1
2
3
4
4-Hydroxy-3-methoxy
benzaldehyde
OH

OMe

2 3
CH C C CH
CH
2
CH
2
CHO
Benzene sulphonic acid
SO
3
H
Nitrobenzene
NO
2

1, 3-Dinitrobenzene
(m-Dinitrobenzene)
NO
2

NO
2

Aniline (Aminobenzene)
NH
2
2-Amino toluene
or
o-Toluidine
CH
3
NH
2
Benzyl amine
or phenyl
methanamine
CH
2
NH
2
4



NO
2
1
2
3
4
3-Chloro-4-methyl nitrobenzene
CH
3
Cl
NH
2
1
2
3
4
5
4-Ethyl-2-methylaniline
CH
3
6
C
2
H
5
1
2
NO
2

O
2
N
3
4
1-Chloro, 2, 4, dinitrobenzene
Cl