6-Special Cases of IUPAC Nomenclature
6-Special Cases of IUPAC Nomenclature
6-Special Cases of IUPAC Nomenclature
BOARDS NEET
Nomenclature of Aromatic Compounds
Aromatic compounds
• These are extra stable compounds that have a cyclic structure along with alternative double
or triple bonds.
• These are less reactive and more stable.
• Benzene (C6H6) is the simplest aromatic hydrocarbon.
• The bond order in benzene is 1.5.
H H
H H H H H
H H
H H H H
H H
H H
H
Resonance structures Resonance hybrid
Resonance in benzene
Examples:
R
If alkyl group is The alkyl group is
Alkyl benzene
added indicated by a prefix.
OH
If OH group is The OH group is
Benzenol
added indicated by a suffix.
NH2
If NH2 group is The NH2 group is
Benzenamine
added indicated by a suffix.
A special suffix
CHO
‘carbaldehyde’ is used
If CHO group Benzene
when the CHO group
is added carbaldehyde
is attached with
benzene.
Note
NO2 Br Cl Cl F
1 2 NO2
6
5 3
4
Nitrobenzene Bromobenzene Chlorobenzene 1-Chloro-2-nitrobenzene Fluorobenzene
A
1
When two substituents are present, their relative
6 1 2
positions are indicated by the prefixes ortho-, meta- o 2 6 o
and para- or by the use of numbers. Ortho position is
denoted by 1,2 position; meta position is denoted by 5 3 5 3
1,3; and para position is denoted by 1,4. m 4 m
4
p
Examples:
CH3 CH3
1 1
2 CH3
6 6 2
5 3 5 3
CH3
4 4
1,2-Dimethylbenzene or o-Dimethylbenzene 1,3-Dimethylbenzene or m-Dimethylbenzene
• When more than two substituents are present on the benzene ring, their positions must be
indicated by the use of numbers.
• The numbering is done in such a way that the substituent gets the lowest possible number.
• When more than two substituents are present and are different, they are written in the
alphabetical order.
Example:
In this case, the parent chain is a benzene ring. All the substituents act as prefixes that have the
same priority order. Therefore, we have to look for the lowest locants first and then the
alphabetical order.
• When a substituent (or functional group) is attached with the benzene ring, it is given a
common name. The substituent (or functional group) is assumed to be in the first position
and a new parent name is used.
Examples:
OH CH3
O
NH2
C OH
OCH3 CHO
Additional examples:
OH OH
1 1
6 2 6 2
5 3 5 3
CH3
4 4
CH3
IUPAC name: 3-Methylphenol IUPAC name: 4-Methylphenol
or m-Methylphenol or p-Methylphenol
Common name: m-Cresol Common name: p-Cresol
COOH OH
1 OH 1
NO2 NO2
6 2 6 2
5 3 5 3
4 4
NO2
IUPAC name: 2-Hydroxybenzoic acid
or 2-Hydroxybenzenecarboxylic acid IUPAC name: 2,4,6-Trinitrophenol
Common name: Salicylic acid Common name: Picric acid
• A hydrocarbon composed of one saturated chain and one benzene ring is usually named as
a derivative of the larger structural unit.
• If an aromatic compound consists of an open and a closed chain, then the principal chain
will be the open chain if it contains multiple bond(s)/ substituent(s)/functional group(s).
Examples:
1 2 3 1 2
H3CCHCH3 HC
CH2
CH3
CH3 CH CH CH2CH3
Write the correct IUPAC name of the given compound.
Solution
1 2 3 4 5
In the given compound, the saturated carbon chain is CH3 CH CH CH2CH3
treated as the parent chain, and the methyl and phenyl
CH3
groups acts as substituents. So, the IUPAC name of the
compound is: 2-methyl-3-phenylpentane
Solution
In the given compound, the benzene ring can be treated as the parent chain and the cyclohexyl
group acts as the substituent or vice versa. So, the IUPAC name of the compound is
cyclohexylbenzene or phenylcyclohexane.
3 2 2 3 3 2 2 3
1 1
4 4 4 4
1 1
5 6 6 5 5 6 6 5
Benzene as parent chain Cyclohexane as parent chain
IUPAC name: Cyclohexylbenzene IUPAC name: Phenylcyclohexane
Examples:
H3C O
3 2 1 2 3 2 6
1
1 6 1 5
4 3 4 2
5 6 5 4 5 6 4 3
Parent chain Parent chain
1-Cyclohexyl-3-methylbenzene 5-Phenylcyclohex-2-en-1-one
The correct IUPAC name for the given compound is: CHO
(a) 5-Bromo-3-hydroxybenzenecarbaldehyde
(b) 3-Bromo-5-fluorophenol
(c) 3-Bromo-5-hydroxybenzenecarbaldehyde
(d) 1-Bromo-3-formyl-5-hydroxybenzene Br OH
Solution
Solution
Examples:
COOH
1. In this compound, the parent chain is a benzoic acid
1
ring. There is an ester group on the third position,
6 2
and it is attached through carbon of the ester group. O
Therefore, the IUPAC name is: 5 3
3-(methoxycarbonyl)benzenecarboxylic acid. C O CH3
4
• When the oxygen atom of an ester is directly attached to the parent chain, the prefix
alkanoyloxy is used in writing the IUPAC name of the ester.
Examples:
O
(I) (II) (III)
Solution
COOH
In compound (I), the C atom of ester is directly attached 1
to the parent chain. So, the prefix alkoxycarbonyl is used 2 C O
6
and it is attached on the second position of the parent
chain. Therefore, its IUPAC name is O
5 3
2-(phenoxycarbonyl)benzenecarboxylic acid.
4
COOH
In compound (II), the C atom of ester is directly attached 1
6 2
to the parent chain. So, the prefix alkoxycarbonyl is used
and it is attached on the third position of the parent
5 3
chain. Therefore, its IUPAC name is C O CH3
3-(methoxycarbonyl)cyclohexanecarboxylic acid. 4
O
In compound (III), the O atom of ester is directly attached COOH
to the parent chain. So, the prefix alkanoyloxy is used 1
and it is attached on the third position of the parent
5 2
chain.Therefore, its IUPAC name is O
3-ethanoyloxycyclopentanecarboxylic acid. 4 3
O C CH3
Solution
In a homologous series, all the members have the same general formula, chemical properties, and
functional group. However, the physical properties such as boiling point, melting point, solubility
etc. tend to vary with variation in molecular mass. Therefore, all the members of a homologous
series show a trend in the physical properties but not exactly the same physical properties.
Thus, option (c) is the correct answer.
Solution
In the compound, there are five carbon atoms in the parent chain. It has a triple bond at the first
position and a double bond at the third position as per the lowest locant rule. Therefore, the
IUPAC name of the compound is pent-3-en-1-yne. 5 4 3 2 1
Thus, option (b) is the correct answer. CH3 CH CH C CH
Solution
Solution
Me
Et
Write the correct IUPAC name of the given
compounds:
(I) (II)
Solution
1 3
In compound (I), the parent chain is cyclobutane and 4 1 2
propyl is the side chain.
IUPAC name: Propylcyclobutane
3 2
Solution
1
In option (d), the numbering should start according
2
to the alphabetical order. So, the ethyl group should 6
get the first priority in numbering. Thus, it is
5 3
incorrect.
Thus, option (c) is the correct answer. 4
Solution
4 3 2 1
HC
C CH
CH2
In the parent chain, there are four carbon atoms. Among the double and triple bonds, the double
bond gets the priority over the triple bond as ene comes first in the alphabetical order compared
to yne. So, the numbering starts from the double bond. Therefore, the IUPAC name of the
compound is but-1-en-3-yne.
Thus, option (c) is the correct answer.
Solution
5 4 3 2 1 1 2 3 4 5 6
(a) H2C CH CH2 C (b) CH CH
CH CH C
CH
CH 3 2
7 6 5 4 3 2 1 1 2 3 4 5 6 7
(c) CH2 CH2 (d) CH2
CH CH2 CH
CH CH CH CH2 C
CH CH CH
Solution
In the numbering of the alkene and alkyne, there are two rules.
• Rule of first point of difference i.e, the numbering should start from the side where the lowest
locant is present.
• If both alkene and alkyne get the same number, then the numbering is done according to the
alphabetical order and alkene gets the priority.
According to these rules, only option (d) has the correct numbering.
Thus, option (d) is the correct answer.
(a) (b) .
(c) (d)
Solution
The correct IUPAC name for the given compound is: H3C CH
CH CH CH
CH2
OH
(a) Hexa-2,5-dien-4-ol (c) Hexa-1,4-dien-3-ol
(b) 3-Hydroxyhexan-1,4-diene (d) 4-Hydroxyhex-2,5-diene
Solution
In the parent chain, there are six carbon atoms. So, the
OH group gets the highest priority. The numbering is 6 5 4 3 2 1
H3C CH
CH CH CH
CH2
done from that side where the OH group as well as the
double bond are getting the lowest number. OH
Thus, option (c) is the correct answer. IUPAC name: Hexa-1,4-dien-3-ol
O
Write the correct IUPAC name of C6H5COCl.
Solution
In this compound, the carbonyl chloride is attached to the benzene ring. Thus, the IUPAC name is
benzenecarbonyl chloride.
Thus, option (c) is the correct answer.
The correct IUPAC name for the given compound is: C3H7 C3H7
Solution
In this compound, there is no fixed structure of C3H7, it could be propyl or isopropyl. Thus, without
any fixed structure of the C3H7 group, we cannot tell the IUPAC name of this compound.
Thus, option (d) is the correct answer.
(a) 4-Ethyl-2-methyl-1-propylcyclohexane
(b) 1-Ethyl-3-methyl-4-propylcyclohexane
(c) 5-Ethyl-1-methyl-2-propylcyclohexane
(d) 1-Methyl-3-ethyl-6-propylcyclohexane
Solution
Solution
Solution
Which of the following is the incorrect IUPAC name for the given structures?
2-Methyl-3-butanone 2, 3-Dimethylpentane
(c) CH3 C
CCH(CH3)2
(d) H3C CH CH CH3
Cl Br
4-Methyl-2-pentyne 3-Chloro-2-bromobutane
Solution
Br CH3
4-Bromo-2,4-dimethylhexane
CH3
O
5-Oxohexanoic acid
2-Methyl-3-phenylpentane
Solution
NH2
HO NH2
HO
SO3H
SO3H
(c) (d) NH2
NH2
OH
OH
Solution