Nomenclature of
Organic Compounds
B. R. Thorat
Govt of Maharashtra
Ismail Yusuf Arts, Science
and
Commerce College,
Mumbai
Sunday, December 4, 2016
[Link]
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
Sunday, December 4, 2016
[Link]
a. Polysubstituted benzenes without functional groups:
1.
2.
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).
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)
Cl
4-chloro-3-methyl
bromobenzene
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CH3
Cl
CH3
3-methyl-5-nitro
chlorobenzene
[Link]
Cl
NO2
NO2
NO2
CH3
Br
(1,2,4-trichlorobenzene)
Cl
4-iodo-3-nitro
chlorobenzene
CH3
2,3-dimethyl
nitrobenzene
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.
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[Link]
COOH
OH
CHO
COOH
Cl
COOH
CH3
NO2
Cl
3-chloro-2-methyl
benzoic acid
2-chloro-5-nitrophenol
CHO
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3-ethylbenzaldehyde
Br
4-chlorobenz-1,2-dioic
acid
OH
COOH
OH
Cl
CHO
benz-1,3-dial
C2H5
Cl
OH
4-chlorobenz-1,2-diol
OH
2-chloro-3-hydroxy
benzoic acid
[Link]
H2N
Cl
3-amino-5-chloro
phenol
Trisubstituted Naphthalene
Numbering in polysubstituted naphthalene, always starts from alphaposition of the ring containing substituted groups or functional
groups is either clockwise or anticlockwise direction.
1
5
1
2
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B
3
[Link]
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).
Cl
4
3
1
6
A
Cl
CH3
A
7
8
Cl
1,2,3-trichloro
naphthalene
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H3C
Cl
B
NO2
Br
4-bromo-1,3-dimethyl
naphthalene
4
3
7
3
Br
3-bromo-1-chloro-2nitronaphthalene
[Link]
NO2
CH3
Br
1-bromo-2-methyl-4nitronaphthalene
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
2,3-dichloro-1naphthol
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OH
Cl
4-chloro-naphtha1,3-diol
Cl
OH
COOH
COOH
3-chloro-4-hydroxy2-naphthoic acid
[Link]
COOH
3-hydroxynaphth-1,2dioic acid
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
OH
Cl
OH
Cl
NO2
Cl
1,2,5-trichloronaphthalene
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NO2 Br
5-bromo-1-chloro
-4-nitronaphthalene
Br
5-bromo-3-nitro
naphthol
[Link]
Br
COOH
4-bromo-5-hydroxy2-naphthoic acid
9
Disubstituted Anthracene
Both the substituents are substituted on same or different rings.
B
The numbering can be done by following the either order depending
on the position of substituent.
4
10
10
4
3
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1
2
2
8
10
1
[Link]
10
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 order.
Cl
Cl
OH
Cl
1,3-dichloroanthracene
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OH
4-chloro-1-anthracenol
[Link]
COOH
10-hydroxy-9-anthranceoic
acid
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
2,10-dichloroanthracene
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OH
Cl
8-chloro-1-anthracenol
[Link]
COOH
4-hydroxy-9-anthracenoic
acid
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.
O
OMe
OMe
2-methoxy-4-methyl
octane
Cl
methoxybenzene
4-phenoxychlorobenzene
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
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14-crown-4
[Link]
16-crown-4
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
O
O
2,2,3,3-tetramethyl
oxirane
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2,2-dimethyloxirane
Cl
Br
Cl
2-bromo-3-chlorooxirane
[Link]
Ph
2-chloro-3-phenyl
oxirane
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
2-cyclohexylethanthiol
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SH
SH
2,3-dimethyl-2-butanthiol
[Link]
cyclopentanthiol
SH
1-phenyl-2-propanthiol
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
2-pentathione
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1-cyclohexyl-2-pentathione 4-phenyl-2-butathione
[Link]
cyclohexathione
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
2-ethyl-1-methyl
butansulfonic acid
2-cyclobiutyl-1-methyl
-ethanthiosulfonic acid
SO3H
SO3H
Benzene
sulfonic acid
2-ethyl-1,2-dimethyl
-butansulfonic acid.
SCH3
H3C
CH3
propylmethylthioether
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CH3
H3C
3-methylthiohexane
[Link]
H3C
CH3
dimethylthioether
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
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[Link]
18
