NOTE

C H E M I S T R Y

GENERAL ORGANIC CHEMISTRY

Types of boundaries
ENTRY OF VVIPS - NOMENCLATURE OF ORGANIC
COMPOUNDS WITH MONO FUNCTIONAL GROUP

What you already know

• IUPAC nomenclature of saturated • IUPAC nomenclature of dienes and

hydrocarbons polyenes
• IUPAC nomenclature of unsaturated • Alkenes and alkynes as substituent groups
compounds
• Types of dienes and polyenes

What you will learn

• Nomenclature of cyclic hydrocarbons • Nomenclature of organic compounds with

• Functional groups functional groups

BOARDS MAIN ADVANCED

Nomenclature of Cyclic Hydrocarbons

Determining the parent chain

Case 1: In cyclic hydrocarbons without substituents

For alicyclic compounds without substituents, the names are obtained by adding the prefix ‘cyclo’.
Examples:

1 2 3

4 2

4 3 5 1
Cyclobutane Cyclopentene (Cyclopent-1-ene)

Case 2: In cyclic hydrocarbons with substituents

• If the number of ‘C’ atoms in the ring ≥ the number of ‘C’ atoms in the open chain, then the ring
is considered to be the parent chain and the open chain is considered to be the substituent.

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Example:
1

The open chain has only one carbon, but the 5 2

ring has five carbons. So, the ring is the parent
chain. The IUPAC name of the compound is
1-Methylcyclopentane.
4 3
1-Methylcyclopentane
(Methylcyclopentane)
• If the number of ‘C’ atoms in the ring < the number of ‘C’ atoms in the open chain, then the ring
is considered to be the substituent and the open chain is considered to be the parent chain.
Example:
1 3 5
The open chain has six carbon atoms and the ring 2 1 2 4
6
has four carbon atoms. So, the open chain is the
parent chain. The IUPAC name of the compound
is 1-Cyclobutylhexane. 3 4
1-Cyclobutylhexane
• If more than one alicyclic ring is attached to a single chain, then the rings are considered to be
the substituents and the attached alkyl group is considered to be the parent chain.
Example:

2 2
Here, two cyclopropyl groups are attached to 1
1 1
the −CH2− group. So, −CH2− group is the parent CH2
chain here. The IUPAC name of the compound is
Dicyclopropylmethane.
3 3
Dicyclopropylmethane
Case 3: In the presence of unsaturation
• If the ring has unsaturation and the open chain is saturated, then the ring is considered to be the
parent chain and the open chain is considered to be a substituent irrespective of the number of
C-atoms.
Example:
6 1

5 1 2

Here, the ring has unsaturation. So, the ring

is the parent chain. So, the IUPAC name is
1-Ethylcyclohexene. 4 2

3
1-Ethylcyclohexene

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• If the open chain has unsaturation and the ring is saturated, then the open chain is considered
to be the parent chain and the ring is considered to be a substituent irrespective of the number
of C-atoms.
Example:
2 1

3 1 2

Here, the open chain has unsaturation. So, the

open chain is the parent chain. So, the IUPAC
name is 1-Cyclohexylethene. 4 6

5
1-Cyclohexylethene
• If both the open chain and the ring have unsaturation, the one with the maximum number of
double or triple bonds is considered to be the parent chain.
Example:

1
2 2 3

Here, the ring contains two double bonds and the 5 1

open chain contains only one double bond. So,
the ring is the parent chain. So, the IUPAC name is
3
5-(Prop-2-enyl)cyclopenta-1,3-diene.
4
5-(Prop-2-enyl)cyclopenta-1,3-diene

• If both the open chain and the ring have equal unsaturation, then the longest one is the parent
chain.
Example:
5 1

Here, the ring contains five carbons and one double 1 2

4
bond, but the open chain contains two carbons
and one double bond. So, the ring is the parent
chain. So, the IUPAC name is 4-Ethenylcyclopent- 2 3
1-ene or 4-Ethenylcyclopentene.
4-Ethenylcyclopent-1-ene or
4-Ethenylcyclopentene

• If both the open chain and the ring have equal unsaturation and equal number of ‘C’ atoms, then
the ring is considered to be the parent chain.

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Example: 1 3
Here, both the ring and the open chain contain 1 4 2
four carbon atoms and one double bond. So, 4
2 3
the ring is the parent chain.Red numbering:
Substituent at 4. Green numbering: Substituent 1 4
at 3. So, the green one is correct because of 2 3
the lowest locant rule. So, the IUPAC name is
3-(But-1-enyl)cyclobutene. 3-(But-1-enyl)cyclobut-1-ene

Based on IUPAC nomenclature

The IUPAC name of the given compound is:

Solution

From the structure given, we can see that the ring is the parent chain (since it contains more
number of carbons than the other substituents i.e. methyl, ethyl and propyl). If numbering is started
from the carbon attached to the methyl group, two possible ways of numbering i.e., 1,3,6 and 1,2,5
are possible. If numbering is started from the carbon attached to the propyl group, then the two
possible ways of numbering are 1,2,4 and 1,4,6. If numbering is started from the carbon attached
to the ethyl group, then the two possible ways of numbering are 1,3,4 and 1,4,5. So, starting the
numbering from the propyl group (1,2,4) is the correct one because of the lowest locant rule.

3 1 6
2 1 5

2 4
2
3 1
So, the IUPAC name of the compound is 4-Ethyl-2-methyl-1-propylcyclohexane.

Assigning locants
Example: 6
5 1
• If more than one double or triple bonds are
present, then they are assigned the lowest
possible number. 4 2
3
1,3-Cyclohexadiene (or) Cyclohexa-1,3-diene

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Example:
3

• If both a multiple bond and a substituent 4 2

are present, then the multiple bond gets the
lower number.
5 1
3-Methylcyclopent-1-ene
(3-Methylcyclopentene)
Example:
• If both double and triple bonds are present,
then alphabetical order is followed in writing 9
the name. 8 7 1
8 10
Green way: 1,4 (1 is given to the double 6 5
bond) Red way: 1,4 (1 is given to the triple 7 9 2
bond) Green is the correct way because 4
double bonds get the priority when the set
10 1 2 3
of positions are the same. So, the IUPAC
6 5 4 3
name is Cyclodec-1-en-4-yne.
Cyclodec-1-en-4-yne

Based on IUPAC nomenclature

The IUPAC name of the given compound is:

Solution

If the number of ‘C’ atoms in the ring < the number of ‘C’ atoms in the open chain, then the ring is
considered to be a substituent and the open chain is considered to be the parent chain. Here, the
open chain contains seven carbon atoms and the ring contains five carbon atoms. So, the open
chain is the parent chain. So, the IUPAC name is 1-(2-Methylcyclopentyl)heptane.

2 1 3 5 7
1 2 4 6
3

4 5
1-(2-Methylcyclopentyl)heptane

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Based on IUPAC nomenclature

The IUPAC name of the given compound is:

Solution

Here, the cyclic ring contains unsaturation. So, it will be the parent chain and the double bond
should get the lowest possible number. So, numbering will start from the double bond. So, the
IUPAC name is 1-Methyl-4-(1-methylethyl)cyclohex-1-ene (or) 4-isopropyl-1-methylcyclohex-1-ene.

2 3 2

1 4 1

6 5
1-Methyl-4-(1-methylethyl)cyclohex-1-ene (or) 4-isopropyl-1-methylcyclohex-1-ene

Based on IUPAC nomenclature

The IUPAC name of the given compound is:

Solution

Here, the ring contains more carbon atoms. So, 5 3

it will be the parent chain. Following the lowest
locant rule, the IUPAC name of the compound is
1,2-Dimethyl-4-methylidenecyclopentane. 1 2

1,2-Dimethyl-4-methylidenecyclopentane

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BOARDS MAIN
Functional Group

A functional group is an atom or a group of atoms bonded together in a unique manner which is
usually the site of chemical reactivity in an organic molecule. The presence of functional groups
enables systematisation of organic compounds into different classes.

Class of compounds Functional group structure IUPAC group suffix

Carboxylic acids −COOH − oic acid/carboxylic acid

Sulphonic acids −SO3H sulphonic acid

Esters −COOR − oate/carboxylate

Acyl Halides −COX − oyl halide/carbonyl halide

Amides −CONH2, −CONHR & −CONR2 − amide/carboxamide

Nitriles −CN −nitrile/carbonitrile

Isonitriles −NC −isonitrile

Aldehydes −CHO −al/carbaldehyde

Ketones >C=O − one

Alcohols −OH − ol

Thiols −SH − thiol

Amines −NH2, −NHR, −NR2 − amine

Alkenes >C=C< − ene

Alkynes −C≡C− − yne

Class of compounds Functional group structure IUPAC group prefix

Ether −OR − alkoxy

Halides −X −halo

Nitro −NO2 −nitro

Nitroso −NO −nitroso

Table 1: Functional groups and their IUPAC suffix & prefix for various class of compounds

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BOARDS MAIN
Nomenclature of Organic Compounds with Functional Group

Carboxylic acids (−COOH)

When −COOH group is a part of the parent chain, then the suffix “ − oic acid” is used. While naming,
the terminal “e” of the primary suffix is usually removed before adding “− oic acid”.
Examples:
O O

1 3 1
C H3C C
2 2
H3C OH CH2 OH
Ethanoic acid Propanoic acid
When −COOH group is not a part of the parent chain, then the suffix “ carboxylic acid” is used.
Example:
O

3 1
OH

4 6

5
Cyclohexanecarboxylic acid

Sulphonic acids (−SO3H)

Suffix: −sulphonic acid

Example:
O OH
O O 2
S
2 1 1
H3C S OH CH3 CH2 S OH 3 O

O O
4 5

Methane sulphonic acid Ethane sulphonic acid Cyclopentane sulphonic acid

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Anhydride (−COOCOR)

When −COOCOR group is a part of the parent chain, the suffix “-oic anhydride” is used. While
naming, the terminal “e” of the primary suffix is usually removed before adding “-oic anhydride”.
Example:

If both the −RCO groups are the same, then just count O O
the total number of carbons of one RCO group and
H3C C O C CH3
name accordingly by adding the suffix “-oic anhydride”. 2 1 1 2
Ethanoic anhydride

Example:
If both the −RCO groups are not the same, then divide O O
it into two parts and name it alphabetically by adding 2 1 1 2 3
the suffix “oic anhydride”. H3C C O C CH2 CH3
Ethanoic propanoic anhydride

Example:

3 3
4 2 2 4
When −COOCOR group is not a part of the parent
1 O 1
chain, then the suffix “-carboxylic anhydride” is used. 5 5
6 O O 6

Cyclohexanecarboxylic anhydride

Esters (−COOR)

When −COOR group is a part of the parent chain, then the suffix “-oate” is used. Alkyl group which
is attached to the O-atom is written first and the second word is the name of the parent acid with
the suffix “-ic acid” replaced by “-ate”.
Example:
O O

1C 1 1 1
CH2 C CH3
2 2
H O CH3 CH3 O

Ethyl methanoate Methyl ethanoate

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Example:
O

2
When −COOR group is not a part of the parent chain, 3 1
then the suffix “-carboxylate” is used. OCH3
4 6
5
Methyl cyclohexanecarboxylate

Acid Halides (−COX)

When −COX group is a part of the parent chain, then the suffix “-oyl halide” is used.
Example:
O O

1 1
2
H3C CI H CI

Ethanoyl chloride Methanoyl chloride

Example:
O

2
When −COX group is not a part of the parent chain, 3 1
then the suffix “-carbonyl halide” is used. CI
4 6
5
Cyclohexanecarbonyl chloride

Amides (−CONH2, −CONHR, −CONR2)

When −CONH2 group is a part of the parent chain, then the suffix “-amide” is used.
Examples:
O O

1
2
H NH2 H3C NH2
Methanamide Ethanamide

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Example:
O

2
When −CONH2 group is not a part of the parent chain, 3 1
then the suffix “-carboxamide” is used. NH2
4 6
5
Cyclohexanecarboxamide

Cyanide (−C≡N)

When −C≡N group is a part of the parent chain, then the suffix “-nitrile” is used.
Examples:
2 1 3 2 1
H3C C N H3C H2C C N
Ethanenitrile Propanenitrile
When −C≡N group is not a part of the parent chain, then the suffix “-carbonitrile” is used.
Example:

2 N
C
3 1

4 6

5
Cyclohexanecarbonitrile

Isocyanide (−NC)

For −N≡C group suffix “-isonitrile” is used.

Example:

N C

2
3 1
H3C N C H3C CH3

Methyl isonitrile Propan-2-isonitrile

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Note

Cyanide and isocyanide are two different functional groups. Also, cyanide has more priority over
isocyanide.

Aldehydes (−CHO)

When −CHO group is a part of the parent chain, then the suffix “-al” is used and the naming of the
aldehyde is derived from the names of the corresponding alkanes by replacing the ending “-e”
with “-al”.
Examples:
O O

1
2
H H H3C H
Methanal Ethanal

When −CHO group is not a part of the parent chain, then the suffix “-carbaldehyde” is used.
Example:
O
2

3 1
H

4 6

5
Cyclohexanecarbaldehyde

Ketones (>C=O)

The IUPAC names of ketones are derived from the names of the corresponding alkanes by replacing
the ending “-e” with “-one”.
Examples:
O O
1 2 3 4 5 4 3 2 1
H3C CH2 C CH2 CH3 H3C CH2 C CH3

Pentan-3-one Butan-2-one

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