Nomenclature of

Organic Compounds

B. R. Thorat
Govt of Maharashtra

Ismail Yusuf Arts,

Science and

Commerce College, Mumbai

Monday, June 24, 2024 B.R.THORAT 1
 IUPAC Nomenclature

Polysubstituted benzenes:
In polysubstituted benzenes, minimum two and maximum six substituents are attached.
These groups are either functional group (-COOH, -HC=O, -C=O, -OH (phenoilc or
alcoholic), -NH2 (amines or anilines), etc; or non-functional groups –CH3, -X
(halogens), -NO2, -OR, etc; identical or different, simple or complex, etc.

a. Polysubstituted benzenes without functional groups:

b. Polysubstituted benzenes with functional groups:

i. One functional group
ii. More than one similar functional group
iii. More than one different functional groups

Monday, June 24, 2024 B.R.THORAT 2

 a. Polysubstituted benzenes without functional groups:

1. When all the substituents are identical, then used the prefix di, tri, tetra, penta,
hexa before the name of the substituent. The numbering is done such that the
substituent carbon has lowest priority (number).
2. When the substituents are different, then they are mentioned in alphabetical
order in the name. The numbering is done such that the substituent carbon has
lowest priority (number). Generally, the first substituent has lowest number.
Cl Cl Cl

Cl Cl

Cl Cl Cl
(1,3,5-trichlorobenzene) (1,2,4-trichlorobenzene) Cl

Cl NO2 NO2
NO2
CH3 CH3
I

CH3
Cl CH3 Cl
Br 4-iodo-3-nitro 2,3-dimethyl
4-chloro-3-methyl 3-methyl-5-nitro nitrobenzene
chlorobenzene chlorobenzene
bromobenzene
Monday, June 24, 2024 B.R.THORAT 3
 b. Polysubstituted benzenes with functional groups:

i. One functional group

When a substituent is a functional group, then it get priority in the nomenclature and
the other substituted atoms or groups are considered as substituents. The name of the
substituents are in alphabetical order. During the numbering, first priority (number) is
given to the carbon to which functional group is attached.

ii. More than one similar functional group

Used the prefixes di, tri, tetra, etc before the name of functional group. During the
numbering follow the priority rule.

iii. More than one different functional groups

If functional groups are not identical, then functional group with higher priority
becomes the root of nomenclature and numbering begins from this functional group.
The other functional groups are considered as substituents. During the numbering,
again fallow the priority rule and alphabetical order of name of substituents.

Monday, June 24, 2024 B.R.THORAT 4

 COOH
OH CHO COOH
COOH
Cl
CH3

NO2 C2H5 Br
Cl
2-chloro-5-nitro- 3-chloro-2-methyl 3-ethylbenzaldehyde 4-chlorobenz-1,2-dioic
phenol benzoic acid acid

CHO COOH OH
OH
Cl
Cl OH
CHO OH H2N Cl
benz-1,3-dial 4-chlorobenz-1,2-diol 2-chloro-3-hydroxy 3-amino-5-chloro
benzoic acid phenol

Monday, June 24, 2024 B.R.THORAT 5

 Trisubstituted Naphthalene
Numbering in polysubstituted naphthalene, always starts from
alpha-position of the ring containing substituted groups or functional
groups is either clockwise or anticlockwise direction.

1 8
4 5
2 7
3 6
A B
A B 6
7 3
2
4 5
1 8

5 4
3 8 1
6
7 2
A B
7 2 A B
6 3
8 1
5 4

Monday, June 24, 2024 B.R.THORAT 6

 Trisubstituted naphthalene, all substituents are on same ring.

1. All the substituents are same, then used prefix tri- before the
name of the substituent. The numbering is done such that
substituent carbon has least priority (number).
2. If two substituents are identical and one different or all
substituents are different, then naming is done in alphabetical
order. The numbering is done to maintaining the least total
(priority principle).
CH3 Cl NO2
4 5 8 8 1 5 4
Cl 3
1 NO2 3
6 2 7 6
7 2
A B A B A B A B 2
7 6 6 7
Cl 2
1 H3C 3 3 Br 1
CH3
8 4 5 5 4 8
Cl Br Br
3-bromo-1-chloro-2- 1-bromo-2-methyl-4-
1,2,3-trichloro 4-bromo-1,3-dimethyl
nitronaphthalene nitronaphthalene
naphthalene naphthalene

Monday, June 24, 2024 B.R.THORAT 7

3. If one of the three substituents is the functional group, then it get
priority during the numbering and nomenclature and its name can be
written after the name of parent (i.e. naphthalene).
4. If more than one substituents are functional groups and are same, then
use prefix di- or tri- before the name of parent compound. The
substituents position can be mention before the name of functional
group or parent compound (after the substituent).
5. Compound containing more than one different functional group, use
priority rule during the nomenclature.
OH OH OH
Cl Cl OH

Cl OH COOH COOH
Cl COOH
2,3-dichloro-1- 3-chloro-4-hydroxy-
naphthol 4-chloro-naphtha- 2-naphthoic acid 3-hydroxynaphth-1,2-
1,3-diol dioic acid

Monday, June 24, 2024 B.R.THORAT 8

Trisubstituted naphthalene, substituents are attached on both ring
1. If all substituents are non-functional, then numbering starts at the
nearest alpha position of the ring containing two substituents,
complete the ring and then on second ring. During nomenclature,
name of the substituents are in alphabetical order and follow the
least priority total.
2. If one substituent is functional group, then give priority to it
during numbering.
3. If more than one functional is present, used priority rule during
naming and numbering.
Cl Cl OH
OH Br
Cl

NO2
COOH
Cl NO2 Br Br
1,2,5-trichloro- 5-bromo-1-chloro 4-bromo-5-hydroxy-
5-bromo-3-nitro
naphthalene -4-nitronaphthalene 2-naphthoic acid
naphthol
Monday, June 24, 2024 B.R.THORAT 9
 Disubstituted Anthracene

Both the substituents are substituted on same or different rings.

A B C

The numbering can be done by following the either order depending

on the position of substituent.
1 9 8
4 10 5
2 7
3 6
C A B C
A B 6
7 3
2
4 10 5
1 9 8

5 10 4 8 9 1
3 7 2
6
A B C A B C
7 2 6 3
1 5 10 4
8 9

Monday, June 24, 2024 B.R.THORAT 10

 Disubstituted anthacene, both substituents are attached on
same ring
1. If both substituents are same then use prefix di-before the name
of substituent. The numbering is done so that both substituent has
least substitution position (priority).
2. If the two substituents are different then naming must follow
alphabetical order and the numbering is done to maintain the
least priority total. If one of the substituent is functional group
and other is not, then functional group gives priority in
nomenclature. Both substituents are functional group, then follow
priority Cl
order. Cl OH

Cl
OH COOH
1,3-dichloroanthracene 10-hydroxy-9-anthranceoic
4-chloro-1-anthracenol
acid
Monday, June 24, 2024 B.R.THORAT 11
 Disubstituted anthracene, both the substituents are attached on two different rings

Both the substituents are functional or non-functional. If substituents

are nonfunctional then do the numbering to follow least priority total.
if one of the substituent is functional group then give the priority to
functional group during numbering. If both or functional group, use
functional group priority order.
OH
Cl

Cl
Cl OH COOH
2,10-dichloroanthracene 4-hydroxy-9-anthracenoic
8-chloro-1-anthracenol
acid

Monday, June 24, 2024 B.R.THORAT 12

 Ethers
Ethers are alkoxy or aryloxy derivative of hydrocarbon i.e. one of the
hydrogen atom is replaced by alkoxy or aryloxy group.
Ethers are therefore named as alkoxyalkane or aryloxyalkane or
alkoxyarenes or aryloxyarenes depending on the size of group attached
to oxygen atom. OMe O

OMe Cl
2-methoxy-4-methyl methoxybenzene 4-phenoxychlorobenzene
octane
If cyclic molecule containing number of ether linkages is called as
crown ether. It is named as x-crown-y; x is total number of atoms in
ring and y is number of oxygen atoms in ether linkage.

O O O O

O O O O
14-crown-4 16-crown-4

Monday, June 24, 2024 B.R.THORAT 13

 Epoxides (oxiranes)
Epoxides are three membered saturated heterocyclic molecules
containing one oxygen atom (as a ring member). The IUPAC name
of epoxides is oxiranes.
Numbering in oxiranes is always starts from oxygen atom and then
towards substituted carbon; if both carbons are substituted the fallow
alphabetical order during nomenclature and same for numbering.

O
O O
Oxirane 2-methyloxirane 2,2-dimethyloxirane

Cl
O
Br Ph
O
O Cl 2-chloro-3-phenyl
2,2,3,3-tetramethyl 2-bromo-3-chloro- oxirane
oxirane oxirane

Monday, June 24, 2024 B.R.THORAT 14

 Sulfur compounds: Thiols
It is derivative of hydrocarbon in which –H is replaced by –SH. It is
represented by: R-SH. The IUPAC nomenclature is similar to alcohol
[Select longest chain; do numbering such that –SH substituted
carbon has least priority and other substituents are considered as
substituents.
During nomenclature ‘e’ replaced by ‘thiol’ with number before the
name of parent compound.
SH
SH SH
SH

2-cyclohexylethanthiol 2,3-dimethyl-2-butanthiol cyclopentanthiol 1-phenyl-2-propanthiol

Monday, June 24, 2024 B.R.THORAT 15

 Sulfur compound: Sulfones
These are compounds containing –C=S group i.e. similar to ketone in
which oxygen replaced by sulfur. The naming of sulfones (called
thiones) is similar to ketones (select the –C=S group and give the
numbering such that carbon of –C=S carbon has lowest priority). Its
name can be derived from hydrocarbon in which ‘ne’ replaced by
‘one’.

S
S
S S

2-pentathione 1-cyclohexyl-2-pentathione 4-phenyl-2-butathione cyclohexathione

Monday, June 24, 2024 B.R.THORAT 16

 Sulfonic acid and thioethers
Sulfonic acids are named as alky sulfonic acids or aryl sulfonic acids.
The numbering starts from the carbon bearing –SO3H group. Other
all rules are similar to carboxylic acid.
Thioethers are named as alkylalkylthioether or alkylthioalkane. The
longenst chain is considered as parent and other is substituent.
SO3H SO3H SO3H
SO3H

2-cyclobiutyl-1-methyl
2-ethyl-1-methyl -ethanthiosulfonic acid Benzene 2-ethyl-1,2-dimethyl
butansulfonic acid sulfonic acid -butansulfonic acid.

SCH3
S
S H3C CH3
H3C CH3 H3C CH3

3-methylthiohexane dimethylthioether
propylmethylthioether

Monday, June 24, 2024 B.R.THORAT 17

Give the IUPAC structure/name of following
(10)

1. 7,8-Dichloro-1-naphthol;
2. 3-chloro-6-iodoanthracene
3. 2,2-diphenyl-3-nitrooxirane
4. n-butyloxycyclohexane
5. 2,4-diamino-benzoic acid
6. 5-chloro-3-nitronaphthyl-2-amine
7. 9-bromo-1-chloroanthracene
8. 18-crown-6
9. BHC
10. 3-nitro-2-bromochlorobenzene

Monday, June 24, 2024 B.R.THORAT 18