NOTE

C H E M I S T R Y

GENERAL ORGANIC CHEMISTRY

IUPAC NOMENCLATURE: A SYSTEMATIC NAMING

What you already know

• Organic compounds • Classification of organic compounds

• Vital force theory • Hydrocarbons
• Bonding in organic compounds • Functional groups
• Why are there countless organic compounds? • Homologous series
• Representation of organic molecules

What you will learn

• Common naming of organic compounds • Degrees of C and H

• IUPAC naming of organic compounds • Nomenclature of saturated hydrocarbons
• Some important alkyl groups (Alkanes)

BOARDS
Nomenclature of Organic Compounds

Every molecule discovered is required to be assigned a name. For example, since we know that
CH3COOH is an organic compound, it is necessary to name it for its reference. Initially, when there
were not many known varieties of organic molecules, it was a common practice to name them on
the basis of their origin or certain properties. Such a name given to the organic compound is known
as its common name.
Examples
(1) Citric acid (Named so because it originated from citrus fruits)
(2) Formic acid (Named so because it originated from red ants)
(3) Acetic acid (It is the chief constituent of vinegar. It is derived from the Latin word ‘acetum’.)
O OH
O O O O

HO OH H OH H3 C OH
OH
Citric acid Formic acid Acetic acid
IUPAC nomenclature
As the discoveries increased, it became difficult to cram random names of such a large number
of molecules. Thus, the standard rules for a systematic naming of the organic compounds are
being set by IUPAC (International Union of Pure and Applied Chemistry). This naming is known as
IUPAC nomenclature. For example, the IUPAC name of CH3COOH is ethanoic acid.

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BOARDS
IUPAC Nomenclature

Consider the name, Mr. Byju Raveendran. It constitutes three parts in which ‘Mr.’ is the prefix, ‘Byju’
is the word root, and ‘Raveendran’ is the suffix.
Mr. Byju Raveendran
Prefix Word root Suffix
Similarly, in the given example, IUPAC names consist of the three following parts:

IUPAC name consists of

Prefix Word root Suffix

Primary Secondary Primary Secondary

Word root: The basic unit of the name that denotes the number of carbon atoms in the parent chain
is known as the word root.

Number of carbon atoms in the parent chain Word root

1 Meth
2 Eth
3 Prop
4 But
5 Pent
6 Hex
7 Hept
8 Oct
9 Non
10 Dec
11 Undec
12 Dodec
13 Tridec
14 Tetradec
15 Pentadec
16 Hexadec
17 Heptadec
18 Octadec
Table 1: Word root for different numbers of carbon atoms

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C Meth
C C Eth
C C C Prop
C C C C But
C C C C C Pent
C C C C C C Hex
C C C C C C C Hept
C C C C C C C C Oct
C C C C C C C C C Non
C C C C C C C C C C Dec
Fig. 1: Word root for parent chain with one carbon atom to ten carbon atoms
Primary suffix: Primary suffixes are added to the root words to show the saturation or unsaturation
in the parent carbon chain.

Type of hydrocarbon Primary suffix General name

Saturated hydrocarbon -ane Alkane

Unsaturated hydrocarbon with one double bond -ene Alkene

Unsaturated hydrocarbon with one triple bond -yne Alkyne

Unsaturated hydrocarbon with a double bond and a triple
-enyne Alkenyne
bond

Table 2: Primary suffix for different hydrocarbon

Secondary suffix: The suffixes that are added after the primary suffix to indicate the presence of a
particular functional group in the carbon chain are known as secondary suffixes.
By using a suffix, the IUPAC name is given as follows:
Word root + Primary suffix + secondary suffix

Examples:

Structure of compound IUPAC nomenclature

H H H H
1 2 3 4 Word root + Primary suffix
H C C C C H But (4 carbon atoms) + ane (0 π bonds)
Compound name: Butane
H H H H
H
H 1 2 3 Word root + Primary suffix
C C C H Prop (3 carbon atoms) + ene (1 π bond)
H Compound name: Propene
H H

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H
1 2 3 Word root + Primary suffix
H C C C H Prop (3 carbon atoms) + yne (1 triple bond)
Compound name: Propyne
H

Word root + Primary suffix

2
3 But (4 carbon atoms) + enyne (1 double and
1 1 triple bond)
4
Compound name: Butenyne

Table 3: Nomenclature of acyclic hydrocarbons

Primary prefix: It distinguishes the cyclic compounds from the acyclic compounds. Generally,
cyclo- is used for cyclic compounds.
By using a prefix and a suffix, the IUPAC name is given as follows:
Primary prefix + Word root + Primary suffix
Examples:

Structure of compound IUPAC nomenclature

1 Primary prefix + Word root + Primary suffix

5 2 Cyclo (Cyclic) + pent (5 carbon atoms)
+ ane (0 π bonds)
4 3 Compound name: Cyclopentane
1 Primary prefix + Word root + Primary suffix
6 2 Cyclo (Cyclic) + hex (6 carbon atoms)
+ ene (1 π bond)
5 3
4 Compound name: Cyclohexene
Table 4: Nomenclature of cyclic hydrocarbons

Based on the IUPAC nomenclature

According to the IUPAC naming rules, what is

the primary suffix used for the given structure?
(a) ane (b) ene
(c) yne (d) yl

Solution

As the compound contains a double bond, the primary suffix should be ene.
Therefore, option (b) is the correct answer.

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BOARDS
Classification of Hydrocarbons

Hydrocarbons

Straight chain Cyclic Branched

Straight-chain hydrocarbons

General formula: Since the valence of each carbon atom is four, in saturated hydrocarbon each
carbon atom is bonded to two hydrogen atoms except terminal carbons, which are bonded to two
more hydrogen atoms (one each). Thus, the general molecular formula of a saturated hydrocarbon
(alkane) can be written as H−(CH2)n−H, i.e., CnH2n + 2
Examples:

Compound name Molecular formula (CnH2n + 2)

Methane CH4
Ethane C2H 6
Propane C 3 H8
Butane C4H10
Pentane C5H12
Hexane C6H14
Heptane C7H16
Octane C8H18
Nonane C9H20
Decane C10H22
Undecane C11H24
Dodecane C12H26
Table 5: IUPAC nomenclature and molecular formulas of alkanes

Cyclic compound

General formula: In cyclic hydrocarbons, the terminal atoms join together. Thus, they have two
hydrogen atoms less than the corresponding acyclic saturated hydrocarbons. Therefore, the general
formula for cyclic saturated hydrocarbon is CnH2n+2 − 2H, i.e., CnH2n.
Examples:

Structure of compound IUPAC nomenclature Molecular formula (CnH2n)

1 2
Cyclobutane C4 H 8
4 3

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1
5 2 Cyclopentane C5H10

4 3

Table 6: IUPAC nomenclature and molecular formulas for cyclic hydrocarbons

Branched hydrocarbons

In branched-chain hydrocarbons, small chains of carbon atoms are attached to one or more carbon
atoms of the parent chain. There is no general formula for branched hydrocarbons.
Example:
CH3 CH CH2 CH3

CH3 Side chain

BOARDS NEET
Alkyl Groups

General formula: These are the univalent groups obtained from saturated hydrocarbons by
removing a hydrogen atom from a carbon atom.
–H
CnH2n+2 CnH2n+1
(Alkane) (Alkyl)
Nomenclature of alkyl groups
During the naming of alkyl groups, the suffix ‘ane’ is replaced by ‘yl’, which converts alkane to alkyl.
The IUPAC nomenclature for alkyl compounds is written as follows:
Word root + Suffix (-yl)
Examples:

Alkyl groups Molecular formula

Methyl −CH3
Ethyl −C2H5
Propyl −C3H7
Butyl −C4H9
Pentyl −C5H11

Table 7: Alkyl groups and their molecular formulas

• Iso group
When one methyl group is attached to the second last carbon atom of the straight-chain, then
the chain is named as an iso group.

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Examples: Isopropyl, isobutyl, etc.

CH3 CH CH3 CH CH2

CH3 CH3
Isopropyl Isobutyl
• Neo group
When two methyl groups are attached to the second last carbon atom of the straight-chain,
then the chain is named as a neo group.
Example: Neopentyl
CH3

CH3 C CH2

CH3
Neopentyl
Some important alkyl groups
• Secondary group
It is represented as ‘sec-’. In this case, the carbon that has one free valency and is attached to
two other carbons. It is known as a secondary group.
Example:

CH3 CH CH2 CH3

sec-Butyl
• Tertiary group
It is represented as ‘tert-’. In this case, the carbon that has one free valency and is attached to
three other carbons. It is known as a tertiary group.
Example:

CH3

CH3 C CH3

tert-Butyl

Note

• No space is used between iso, neo, and the alkyl group.

• There is always a hyphen after sec- or tert-.
• 'I' of iso and 'N' of neo can be written in block letters but not ‘s’ of sec- and ‘t’ of tert-.
• The name of the alkyl group starts with a block letter after sec- or tert-.
• For alphabetical ordering, 'I' of Iso and 'N' of Neo are considered but sec- and tert- are not.

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BOARDS
Degrees of Carbon and Hydrogen

Degree of carbon

1o C 2o C 3o C 4o C
(Primary) (Secondary) (Tertiary) (Quaternary)

Attached with Attached Attached Attached

1C Only with 2C with 3C with 4C

Examples:
Primary Secondary C Tertiary C Quaternary C
H
Carbon Carbon Carbon Carbon

C C H C C H C C H C C C

H H C C

Fig. 2: Degrees of carbon atoms

Degree of hydrogen

1o H 2o H 3o H
(Primary) (Secondary) (Tertiary)

Attached Attached Attached

with 1o C with 2o C with 3o C

Primary Secondary Tertiary

Primary C C
H hydrogen hydrogen hydrogen
hydrogen

C C H C C H C C H

Primary Secondary
H H C
hydrogen hydrogen

Fig. 3: Degrees of hydrogen atoms

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Note

A 4° (quaternary) carbon exists, but a 4° hydrogen does not because a 4° (quaternary) carbon does
not have any hydrogen.

Based on the identification of the degrees of carbon atoms

CH3
Identify and count the degrees of all the carbons
CH3 CH2 CH C CH2 CH3
in the given compound.
CH3 CH3

Solution
1o
CH3
1o 2o 3o 4o 2o 1o
CH3 CH2 CH C CH2 CH3

CH3 CH3
1o 1o

Number of 1° carbon Number of 2° carbon Number of 3° carbon Number of 4° carbon

5 2 1 1

Based on the identification of the degrees of hydrogen atoms

CH3
Identify and count the degrees of all the
CH3 CH2 CH C CH2 CH3
hydrogens in the given compound.
CH3 CH3

Solution
1o
CH3
1o 2o 3o 4o 2o 1o
CH3 CH2 CH C CH2 CH3

CH3 CH3
1o 1o

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Number of 1° hydrogen Number of 2° hydrogen Number of 3° hydrogen

Number of 1° carbon × 3
(Since three hydrogen atoms
are attached to the primary
carbon)
1° carbon = 5
1° hydrogen = 5 × 3 = 15
Number of 2° carbon × 2
Number of 3° carbon × 1
(Since two hydrogen atoms
(Since one hydrogen atom is
are attached to the secondary
attached to the tertiary carbon)
carbon)
2° carbon = 2 3° carbon = 1
2° hydrogen = 2 × 2 = 4 3 hydrogen = 1 × 1 = 1
o

Based on the identification of the degrees of carbon atoms

How many 3o carbon atoms are present in the

given compound?
(a) Five (b) One
(c) Seven (d) Four

Solution
2o 2o 1o
Only one 3 carbon atom is present in the given
o 3o

hydrocarbon. 1o 2o
Therefore, option (b) is the correct answer. 2o
1o

Based on the identification of the degrees of hydrogen atoms

What is/are the number of 3o hydrogen atoms in

the given compound? H3C CH CH3
(a) One (b) Ten
CH3
(c) Nine (d) Six

Solution
Since there is only one tertiary carbon atom 1o 3o 1o
in the given compound, the number of tertiary H3C CH CH3
hydrogen is only one. 1o
Therefore, option (a) is the correct answer. CH3

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BOARDS NEET
Nomenclature of Saturated Hydrocarbons
(Alkanes)

Rule 1: Determining the parent chain that is the longest continuous carbon chain
Select the longest, continuous carbon chain in the molecule. This chain is known as the parent
chain, main chain, or principal chain. It may or may not be straight.
Examples:

Structure of the compound Selection of the parent chain

CH3
1 2 3 4 5 6 7 Here, the horizontal straight-chain that
CH3 CH CH2 CH2 C CH2 CH3 contains seven carbon atoms is the longest
chain. Hence, it is the parent chain.
CH3 CH3
CH3 CH3
5 4 3 2 1
CH3 C CH2 CH2 C CH3
6 Here, the longest zig-zag chain consists of
CH2 CH3 eight carbon atoms. Hence, it is the parent
7 chain.
CH2
8
CH3
4 2
5 3 1 Here, the longest chain is of 11 carbon
6 8 10 atoms. Hence, it is the parent chain.
7 9 11
1
2
3 Here, the longest chain is of nine carbon
4 atoms. Hence, it is the parent chain.
5 7 9
6 8
Table 8: Determining parent chain

Rule 2: Deciding on the parent chain when the chains are of equal lengths
When the two or more chains of equal lengths are competing for selection, then the chain that has
more number of substituents/branches is selected.
Example:

Structure of the compound Selection of the parent chain

1 2 3 4 5 6
C C C C C C
Here, the horizontal, straight-chain contains
C C six atoms and there is only one side chain.
Side chain
C

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3 4 5 6
C C C C C C Here, the zig-zag chain also consists
of six carbon atoms and there are two
2C C Side chain side chains. Hence, this parent chain is
Side chain preferred.
1C
Table 9: Determining parent chain when equal chain lengths are present

Rule 3: Chains with equal number of substituents

When the number of substituents are the same, then the substituents at the nearest positions from
either ends are preferred for the selection of the parent chain.
Example:

Structure of the compound Selection of the parent chain

Substituent
1 3
2 Here, the zig-zag chain consists of
4 eight carbon atoms with two side
5 chains. These side chains are present
6 on the third and fourth carbon atoms.
7 Substituent
8
Here, the zig-zag chain also consists
3 1 of eight carbon atoms with two side
2 chains. These side chains are present
4 on the second and fourth carbon
5 atoms. So, in this case, the position of
Substituent the substituents is closer.
6
Therefore, this parent chain is
7 prefered.
8 Substituent
Table 10: Determination of parent chain by substituents positions

Rule 4: Numbering the parent chain

If two substituents are found in the parent chain, then the one coming first in the alphabetical
order is given the lower number.
Example:

Structure of the compound Selection of parent chain

2
1
Here, methyl is coming at number four and ethyl is present
at number six.
8 6 4 2
9 7 5 3 1

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2 Here, ethyl is given number four and methyl is given

1
number six. Alphabetically, 'e' comes before 'm'. Hence,
'e' will be given priority. Thus, this numbering of parent
2 4 6 8 chain is prefered.
1 3 5 7 9

Table 11: Determination of parent chain by alphabetical order of substituents

Based on the selection of the parent chain

Which of the following correctly represents the parent chain?

(a) CH3

CH3 CH2 CH CH CH2 CH2 CH3

CH CH2 CH3

CH3
(b) CH3

CH3 CH2 CH CH CH2 CH2 CH3

CH CH2 CH3

CH3
(c) CH3

CH3 CH2 CH CH CH2 CH2 CH3

CH CH2 CH3

CH3

(d)
CH3

CH3 CH2 CH CH CH2 CH2 CH3

CH CH2 CH3

CH3

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Solution
(a) The given chain has seven carbon atoms and three branches.
(b) The given chain has seven carbon atoms and two branches.
(c) The given chain has six carbon atoms and three branches.
(d) The given chain has four carbon atoms and one branch.
Therefore, option (a) is the correct answer.

Based on the selection of the parent chain

How many alkyl groups are present on the C C C

parent chain of the given skeleton?
C C C C C C C C C
(a) One (b) Five
(c) Four (d) Three C C C C

Solution
Side chain

C C C
The longest carbon chain is of nine carbons 1 2 4 5 6 8 9
3 7
and has four side chains. Hence, it is the parent C C C C C C C C C
chain.
C C C C

Side chain
Thus, option (c) is the correct answer.

Based on the type of alkyl group

What is the name of the given structure of the CH3

alkyl group?
(a) Isobutyl (b) sec-Butyl CH3 C CH2 CH3
(c) Tertiary pentyl (d) Butyl

Solution

The compound contains a total of five carbon atoms and one carbon atom is connected to three
carbon atoms. Thus, it is tertiary pentyl.
Therefore, option (c) is the correct answer.

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Based on the types of alkanes

Which of the following is a branched alkane?

(a) (b) (c) (d) None of these

Solution
Option (a) has a straight chain with four carbon atoms.
Option (b) has one branched chain connected to the parent carbon chain.
Option (c) has a straight chain with three carbon atoms.
Therefore, option (b) is the correct answer.

Based on identification of the hydrogen atom

How many 1o hydrogen atom(s) is/are present in

the given compound?
CH3 CH2 CH2 CH3
(a) Six (b) Five
(c) Ten (d) Four

Solution

Only the first and the last carbon of the compound H H H H

is connected to only one carbon. Thus, the 1
o
2o
2o
1o
number of the 1o carbon and 1o hydrogen atoms H C C C C H
are two and six, respectively.
Therefore, option (a) is the correct answer. H H H H

Based on the types of alkyl group

What is the name of the alkyl group of the given CH3

structure?
CH3 C CH2
(a) sec-Butyl (b) Neopentyl
(c) tert-Butyl (d) Pentyl CH3

Solution

Since two methyl groups are attached to the second last carbon atom, the name of the group is
neopentyl.
Hence, option (b) is the correct answer.

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Based on the identification of the carbon atom

How many 2o carbon atoms are present in the

given structure?
(a) Eight (b) Two
(c) Four (d) Three

Solution

2o carbon atoms are those that are connected 1o 1o

1o 3o
to two other carbon atoms. So, there are four 2o
carbon atoms in the given compound.
Therefore, option (c) is the correct answer. 2o 3o 2o
2o 2o 1o

Based on the selection of the parent chain

What is the minimum number of carbon atoms in a branched alkane?

(a) Three (b) Four (c) Two (d) Five

Solution
If up to three carbon atoms bond together, they will always lie in a single
chain. In the case of four carbon atoms, methyl can be attached to the second
carbon of the propane chain to give isobutane. So, the minimum number of
carbon atoms required is four.
Therefore, option (b) is the correct answer.

Based on finding the word root

Identify the word root used for the given

skeleton. C C C C C C C C C
(a) Non (b) Hept
C C C
(c) Oct (d) Dec

Solution
1 2 3 4 5 6 7 8 9
C C C C C C C C C

C C C
Since the longest chain in the given compound is of nine carbon atoms, the word root will be non.
Therefore, option (a) is the correct answer.

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Based on the numbering of the parent chain

Which of the following structures has the correct order of numbering the parent chain?

1 3 1 3
(a) 2 4 (b) 2 4
5 6

5
5
4
6 4 1 3
(c) 5 3 (d) 2
2 1

Solution

In option (a), the chain has six carbon atoms and four branches. Also, the ethyl is given priority over
the methyl while numbering. Thus, it is a correct option.
In option (b), the chain has five carbon atoms. So, it cannot be a parent chain. Thus, it is an incorrect
option.
In option (c), the chain has six carbon atoms and four branches. However, here, the methyl is given
priority over the ethyl. Thus, it is an incorrect option.
In option (d), the chain has five carbon atoms. So, it cannot be a parent chain. Thus, it is an incorrect
option.
Therefore, option (a) is the correct answer.

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