NOMENCLATURE

A systematic method of naming organic or

inorganic chemical compounds as
recommended by the International Union of
Pure and Applied Chemistry (IUPAC)

IUPAC nomenclature of Organic

Chemistry
Ideally, every organic compound should have
a name from which an unambiguous
structural formula can be drawn.
The structural formulas of organic compounds
can be written in many ways.

For convenience, condenced structural

formulas are most frequently used
Ethane :
H H
 
H–C–C–H CH3 – CH3 or CH3 CH3
 
H H “Condenced structural formulas

“Drawn out” structure

The main idea of IUPAC nomenclature :
every compound has one and only one name,
and every name corresponds to only one
structure of molecules (i.e. a one-one
relationship), thereby reducing ambiguity.

A. Hydrocarbon
• Acyclic Hydrocarbons
• Monocyclic Hydrocarbons
• Fused Polycyclic Hydrocarbons
• Bridged Hydrocarbons (Extension of the Von
Baeyer System)
• Spiro Hydrocarbons
• Hydrocarbon Ring Assemblies
• Cyclic Hydrocarbons with Side Chains
• Terpene Hydrocarbons

Acyclic Hydrocarbons

Rule A-1. Saturated Unbranched-chain

Compounds and Univalent Radicals

1.1 - The first four saturated unbranched acyclic

hydrocarbons are called methane, ethane,
propane and butane.
The generic name of saturated acyclic
hydrocarbons (branched or unbranched) is
"alkane"

Examples of names:
11 Undecane 22 Docosane 32 Dotriacontane
12 Dodecane 23 Tricosane 33 Tritriacontane
13 Tridecane 24 Tetracosane 40 Tetracontane
14 Tetradecane 25 Pentacosane 50 Pentacontane
15 Pentadecane 26 Hexacosane 60 Hexacontane
16 Hexadecane 27 Heptacosane 70 Heptacontane
17 Heptadecane 28 Octacosane 80 Octacontane
18 Octadecane 29 Nonacosane 90 Nonacontane
19 Nonadecane 30 Triacontane 100 Hectane
20 Icosane 31 Hentriacontane 132 Dotriacontahectane
21 Henicosane
1.2 . Univalent radicals derived from
saturated unbranched acyclic
hydrocarbons by removal of hydrogen
from a terminal carbon atom are named
by replacing the ending "-ane" of the
name of the hydrocarbon by "-yl".

The carbon atom with the free valence is

numbered as 1.

As a class, these radicals are called

normal, or unbranched chain, alkyls.
Examples:
Rule A-2. Saturated Branched-chain
Compounds and Univalent
Radicals
2.1 - A saturated branched acyclic hydrocarbon is
named by prefixing the designations of the side
chains to the name of the longest chain present in
the formula.
Example:
The following names are retained for
unsubstituted hydrocarbons only:

Isobutane

Isopentane

Neopentane

Isohexane
2.2 - The longest chain is numbered from one
end to the other by Arabic numerals, the
direction being so chosen as to give the
lowest numbers possible to the side chains.

When series of locants containing the same

number of terms are compared term by
term, that series is "lowest" which contains
the lowest number on the occasion of the
first difference.

This principle is applied irrespective of the

nature of the substituents.
Examples
Univalent branched radicals derived from
alkanes are named by prefixing the
designation of the side chains to the name of
the unbranched alkyl radical possessing the
longest possible chain starting from the
carbon atom with the free valence, the said
atom being numbered as 1
Examples

1-Methylpentyl

2-Methylpentyl

5-Methylhexyl
The following names may be used for
the unsubstituted radicals only:

Isopropyl Isobutyl sec-Butyl tert-Butyl

Isopentyl Neopentyl tert-Pentyl Isohexyl

2.3 - If two or more side chains of different
nature are present, they are cited in
alphabetical order

The alphabetical order is decided as follows:

(i) The names of simple radicals are first
alphabetized and the multiplying prefixes
are then inserted.

Example :
ethyl is cited before methyl

4-Ethyl-3,3-dimethylheptane
Hypenated prefixes (sec-, tert-) or prefixes
indicaing the number of such groups (di, tri,
etc.) are not considered in alphabetical order

Example:

3-ethyl-6-isopropyl-2,4-dimethylnonane
(alphabetical order : e, i, m)
(ii) The name of a complex radical is
considered to begin with the first letter of
its complete name.
Example:

dimethylpentyl (as complete single

substituent) is alphabetized under d,
thus 7-(1,2-Dimethylpentyl)-5-ethyltridecane
(iii) In cases where names of complex radicals
are composed of identical words, priority for
citation is given to that radical which contains
the lowest locant at the first cited point of
difference in the radical.
Example:
2.4 - If two or more side chains are in equivalent
positions, the one to be assigned the lower
number is that cited first in the name.
Example:
2.5 - The presence of identical unsubstituted
radicals is indicated by the appropriate
multiplying prefix di-, tri-, tetra-, penta-,
hexa-, hepta-, octa-, nona-, deca-,
undeca, etc.
Example:
The presence of identical radicals each
substituted in the same way may be indicated
by the appropriate multiplying prefix bis-, tris-,
tetrakis-, pentakis-, etc.

The complete expression denoting such a side

chain may be enclosed in parentheses or the
carbon atoms in side chains may be indicated
by primed numbers.
Example

(a) Use of parentheses and unprimed

numbers:
5,5-Bis(1,1-dimethylpropyl)-2-methyldecane
(b) Use of primes:
5,5-Bis-1',1'-dimethylpropyl-2-methyldecane
(a) Use of parentheses and unprimed numbers:
7-(1,1-Dimethylbutyl)-7-(1,1-dimethylpentyl)
tridecane
(b) Use of primes:
7-1',1'-Dimethylbutyl-7-1",1"-dimethylpentyltridecane
2.6 - If chains of equal length are competing for
selection as main chain in a saturated
branched acyclic hydrocarbon, then the
choice goes in series to:

(a) The chain which has the greatest number of

side chains.
Example:
(b) The chain whose side chains have the
lowest-numbered locants.
Example:
(c) The chain having the greatest number of
carbon atoms in the smaller side chains.

Example:
(d) The chain having the least branched side
chains
Example:
Rule A-3. Unsaturated Compounds and
Univalent Radicals.
3.1 - Unsaturated unbranched acyclic
hydrocarbons having one double bond
are named by replacing the ending "-ane"
of the name of the corresponding
saturated hydrocarbon with the ending "-
ene".
If there are two or more double bonds, the
ending will be "-adiene", "-atriene", etc.

The generic names of these hydrocarbons

(branched or unbranched) are "alkene",
"alkadiene", "alkatriene", etc.

The chain is so numbered as to give the lowest

possible numbers to the double bonds.
When, in cyclic compounds or their substitution
products, the locants of a double bond differ by
unity, only the lower locant is cited in the name;
when they differ by more than unity, one locant
is placed in parentheses after the other.

Example:

2-hexene

1,4-hexadiene
The following non-systematic names are
retained:

Ethylene

Allene
3.2 - Unsaturated unbranched acyclic
hydrocarbons having one triple bond are
named by replacing the ending "-ane" of the
name of the corresponding saturated
hydrocarbon with the ending "-yne".

If there are two or more triple bonds, the

ending will be "-adiyne", "atriyne", etc.

The generic names of these hydrocarbons

(branched or unbranched) are "alkyne",
"alkadiyne", "alkatriyne", etc.
The chain is so numbered as to give the
lowest possible numbers to the triple
bonds. Only the lower locant for a triple
bond is cited in the name of a compound.

The name "acetylene" for

is retained.
3.3 - Unsaturated unbranched acyclic
hydrocarbons having both double and
triple bonds are named by replacing the
ending "-ane" of the name of the
corresponding saturated hydrocarbon
with the ending "-enyne", "-adienyne", "-
atrienyne", "-enediyne", etcNumbers as
low as possible are given to double and
triple bonds even though this may at
times give "-yne" a lower number than "-
ene".
 When there is a choice in numbering, the
double bonds are given the lowest
numbers.

Example:

1,3-Hexadien-5-yne

3-Penten-1-yne

1-Penten-4-yne
3.4 - Unsaturated branched acyclic
hydrocarbons are named as derivatives of
the unbranched hydrocarbons which
contain the maximum number of double
and triple bonds.

If there are two or more chains competing

for selection as the chain with the maximum
number of unsaturated bonds, then the
choice goes to :

(1) that one with the greatest number of

carbon atoms
(2) the number of carbon atoms being
equal, that one containing the
maximum number of double bonds.
In other respects, the same principles
apply as for naming saturated
branched acyclic hydrocarbons.
The chain is so numbered as to give
the lowest possible numbers to double
and triple bonds in accordance with
Rule A-3.3.
Examples.
The following name is retained for the
unsubstituted compound only:
3.5 - The names of univalent radicals derived
from unsaturated acyclic hydrocarbons
have the endings "-enyl", "-ynyl", "-dienyl",
etc., the positions of the double and triple
bonds being indicated where necessary.
The carbon atom with the free valence is
numbered as 1.

Ethynyl
2-Propynyl

1-Propenyl
2-Butenyl

1,3-Butadienyl

2-pentenyl

2-Penten-4-ynyl
Exceptions:

The following names are retained (for

unsubstituted radical only):

Vinyl (for ethenyl)

Allyl (for 2-propenyl)

Isopropenyl(for 1-methylvinyl)
3.6 - When there is a choice for the
fundamental chain of a radical, that chain
is selected which contains
(1) the maximum number of double and
triple bonds;
(2) the largest number of carbon atoms;
and
(3) the largest number of double bonds.
Examples:
3.6 - When there is a choice for the
fundamental chain of a radical, that chain
is selected which contains
(1) the maximum number of double and
triple bonds;
(2) the largest number of carbon atoms;
and
(3) the largest number of double bonds.