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Arihant Iupac Nomenclatures PDF
Arihant Iupac Nomenclatures PDF
Nomenclature
In this Chapter, we will develop the knowledge of
using IUPAC conventions for naming an organic
compound and to write the appropriate structure of
a compound from its given IUPAC name.
of Organic
Compounds
Learning Framework
of the Chapter . . .
1-1 Introduction
1-2 Naming Hydrocarbons According to IUPAC
Conventions
1-3 Naming Compounds Containing One or More
Similar Type of Principal Functional Groups
1-4 Naming Compounds Containing More Than
One Type of Principal Functional Groups
1-5 Nomenclature of Bicyclic Compounds
1-6 Nomenclature of Spiro Compounds
1-1 Introduction
Because of infinitely large number of organic compounds
existing already and several new compounds being either
synthesized or discovered everyday, each specific compound
requires a unique name so that it can be recognized all over the
world by that name. Just as each distinct compound has a unique
molecular structure which can be designated by a structural
formula, so each compound must be given a characteristic and
unique name.
2 Essential Organic Chemistry
As organic chemistry grew and developed, many compounds were given trivial names, which are now commonly used
and recognized. Some examples are
Name Methane Butane Acetone Toluene Acetylene Ethyl alcohol
Formula CH4 C4H10 CH3COCH3 CH3C6H5 C2H2 C2H5OH
Such common names often have their origin in the history of the science and the natural sources of specific compounds, but
the relationship of these names to each other is arbitrary, and no rational or systematic principles underly their assignments.
Earlier, organic compounds were named on the basis of their source or after the name of discoverer. Due to their large
number, it has becoming difficult for the scientific world to keep record of all organic compounds having typical names
originating from source, discoverer or place of discovery etc.
In order to keep track of such a large number of organic compounds with a wide range in complexity of their skeleton,
the “International Union of Pure and Applied Chemistry” (IUPAC) has set-up some standard conventions for systematic
naming of organic compounds so that they can be easily recognized from their names and their structure can be drawn using
IUPAC conventions.
H H HH
H H HH
C HH H
CH3 H H H H C H H H H C H
H—C—C—C—C—C—C—C—H H C C C H
H3C—CH—CH2CH2—C—CH2CH3 C C C C
CH3 CH3 H C H H C H H H H H
H H C H
2, 5, 5-trimethyl heptane H H
HH HH H HH
As shown in the above structures, carbon is tetravalent and associated with four covalent bonds (C—H or C—C bonds).
H H
H C H
C C H H H
H H =
H H H—C—C—C == C—H=
C C
H C H H C H
H H H HH
Cyclohexane 3-methyl-1-butene
4 Essential Organic Chemistry
H 3C CH3
(1) CH3
Longest chain has seven carbon atoms. If we start numbering from the left terminal, side chain methyl group comes at 5th
carbon while if numbering starts from right terminal, side chain methyl group comes at 3rd carbon which is a lower number.
Hence, the correct way of numbering will be to start from the right terminal.
When more than one locants (side groups) are present, than that number series is “Correct” which contain the lowest
number on the occasion of first difference as
CH3
H 3C
CH3
CH3 CH 3
(2)
The two number series existing in compound (2) are 2,3,5 and 2,4,5. The first one is correct and second is incorrect.
Rule 3 When writing names of branched, saturated hydrocarbon, locants are written first in alphabetical order (irrespec-
tive of their numbers) followed by name of parent chain. Locants in the name must be followed by its number separated by
hyphen (-). If more than one locants of similar types are present at the same or different positions, di, tri etc. are prefixed
before the locants. Adjacent numbers must be separated by comma (,).
Applying the above mentioned rules, compounds (1) and (2) described just before can be named as
CH3
6 4 2 6 4
7 5 3 1 H 3C 5 3 2
1
H 3C CH3 CH3
CH3 CH3 CH3
3-methylheptane 2, 3, 5-trimethyl hexane
(not 2, 4, 5-trimethyl hexane)
Some other examples applying the above rules are
CH3
CH3 CH3 CH3
8
H3C 9
6 1
CH3 CH3 7 5 4 3 2
8 H3C H 3C CH3
9 5 3 1
H3C 6 4 2 CH3
7 CH3 H3C
6-ethyl-2, 4-dimethyl nonane 4-ethyl-2, 3, 6, 6, 8-pentamethyl-5-propylnonane
(not 2,4-dimethyl-6-ethylnonane) (not 6-ethyl-2, 4, 4, 7, 8-pentamethyl-5-propylnonane)
(In alphabetical order, initials of original
name of the locant is considered ie, ‘m’
of methyl is considered here not ‘d’ of di)
Nomenclature of Organic Compounds Chapter 1 5
Rule 4 When two different alkyl locants are equidistant from the two ends of main chain, they are numbered in
alphabetical order as
CH3 CH3
CH3 1
9 10
H3C 5 CH3 8
H3C 7 6 5 4 3 2 1
7 3
8 6 4 2 CH 9 3
CH3
3-ethyl-7-methylnonane 4-ethyl-7-propyldecane
(not 3-methyl-7-ethylnonane) (not 7-ethyl-4-propyldecane)
Rule 5 Following common names are retained in IUPAC system for unsubstituted hydrocarbons only
CH3 CH3 CH3 CH3
CH3 H3C CH3
H3C CH3 H3C H3C CH3
CH3
Isobutane Isopentane Neopentane Isohexane
Rule 6 Branching in the branch: If there is a complex branch which is branched further, branch is numbered separately
starting from the carbon directly bonded to parent chain and name of branch is written in small parenthesis ( ) before the name
of parent hydrocarbon as
12 10 8 6 4 2
13 11 7 5 1
H3C 9 3 CH3
5
H3C 3
2
1 Here the branch is dimethylpentyl as
4
CH3 CH3
complete single substituent
CH3
7-(1, 2-dimethylpentyl)-5-ethyltridecane [not 5-ethyl-7-(1,2-dimethylpentyl) tridecane]
In case where name of complex branch are composed of identical words, priority is given to that branch which has locants
at the lowest number as
4
H3C 3 2
4
H3C 3 CH3 CH3
2 1
H3C 1 8 7
4
3 CH3
1 5
H3C 6 2
12 10 6 4 2
13
8
H3C 11 9 7 5 3 CH3 H3 C CH3
6-(1-methylbutyl)-8-(2-methylbutyl) tridecane 4-isopropyl-5-propyloctane
Both branch have the common word ‘‘butyl’’ therefore, branch at position 6
will have priority since, it has locant at C-1 while other has locant at C-2
Rule 7 The presence of identical complex branch, each substituted in the same way, may be indicated by the appropriate
multiplying prefix bis, tris, tetrakis, pentakis etc. The complete expression denoting such side chain may be enclosed in
parenthesis as
3
CH3 4
2 H3C 2 CH3
3
1 1 CH3
H3 C CH3
6 54
CH3 12 10 6
8 7 3 13
8 CH3
10 9 2 H3C 11 9 7
H3C 1 CH3
H3 C CH3 1 H3 C CH3
2 1
H3C 3 4 5
H3C 2
3
5,5-bis(1, 1-dimethylpropyl)-2-methyldecane 5,5-dimethyl-6-(1,1-dimethylbutyl)-6-pentyltridecane
6 Essential Organic Chemistry
Rule 8 If chains of equal length are competing for selection as main chain in a saturated, branched acyclic hydrocarbons,
the choice goes in series to
(a) The chain, which has the greatest number of side chains
7 6 7 6
H3C H3C 5 H3C 5
CH3 CH3 CH3
6 2
7 5 3 3 1 3
4 2 4 2 4
H3C CH3 H3 C CH3 H3 C CH3
1 1
CH3 CH3 CH3 CH3 CH3 CH3
(b) The chain whose side chain has lowest numbered locants
CH3 CH3
7 6
H3C H3C 5
CH3 CH3
6
7 5 3 3
4 2 4 2
H3C CH3 H3C CH3
1 1
CH3 CH3
Correctly numbered (locants are at Wrongly numbered : locants
2,4,5 positions) 4-isopropyl-2,5- are at 2,4,6 positions
dimethylheptane
(c) The chain having the greatest number of carbon atoms in the smaller side chain
H3C
H3C
H3C
12 10 6 2
13 11 9 5 3 1
8 7 4
H3 C CH3
CH3 CH3 CH3
CH3
H3C
CH3 CH3
7,7-Bis(2,4-dimethylhexyl)-3-ethyl-5,9,11-trimethyltridecane
I II III
IV V
6 4 2 2 4 6
7 5 3 1 5
1 3 7
I II
3-ethyl-5-methylheptane 5-ethyl-3,3-dimethyl heptane
When same number series (here 3,5) are Lower number coming at first occasion of
obtained from both terminals, preference difference determine the numbering
goes to alphabetical order. pattern-here 3,3,5 not 3,5,5.
3 1
4
2 8 2
9 7 5
1 4 6
3 5 7 10
8 6
III IV
6-ethyl-3,4-dimethyl octane 5-butyl-5-methyl-4-propyl decane
Longest chain with maximum number of locants
becomes the parent chain.
4
3 5
2
1 6 7
V
3,5-diethyl-2,3,5,6-tetramethyl heptane
Longest chain with maximum number of locants becomes the parent chain.
I II III
IV V
8 Essential Organic Chemistry
I II
III IV
3
2
1
8 4 2
9 7 6
3 1
2 4 8 10
5 5 6 7
2 3 1 3 9
1
I II
5-(1-ethyl-2, 2-dimethylpropyl)-5 5-(1, 1-dimethylpropyl)-6-
-(1, 2, 2-trimethylpropyl) nonane (2, 2-dimethylpropyl) decane
2
10
3 1 9 7
6 11 8
7 4
4 3
5 6
8 10 5
2
9
1
III IV
8-ethyl-2, 3, 8-trimethyl-4, 7-dipropyl decane 6, 7, 8-triethyl-3-methyl undecane
Problem 1-4 Draw structures of all alkanes and write their IUPAC name having molecular formula C7H16.
Heptane 2-methylhexane 3-methylhexane 2,2-dimethylpentane
Rule 3 Unsaturated unbranched acyclic hydrocarbons, having both double and triple bonds are named by replacing
ending “-ane” from the name of the corresponding saturated hydrocarbons by “-enyne”, “-adienyne”, “-atrienyne” “-enediyne”
etc. Numbers as low as possible are given to double and triple bonds even though this at times gives “-yne” a lower number
than “-ene”.
6
2 4 2 4
CH
H2C 3 5 HC 3 CH3
1 1 5
1,3-hexadien-5-yne 3-penten -1-yne
Preference has been given to numbering 1,3 rather than to 2,4 and not to triple bond over double bond.
Rule 4 When there is a choice in numbering between double and triple bond (this occur when double and triple bonds
are equidistant from the two terminal), the double bonds are given lowest numbers(ene comes before yne in alphabetical
order).
1
4 2 7 5 3 CH3
5 1 8 4
HC 3 CH2 H3 C 6 2
CH3
1-penten-4-yne 4-methyl-6-octen-2-yne
Here both double bond and triple bonds are Here both double bond and triple bonds are
equidistant from terminals hence, numbering is equidistant from terminals hence, preference
done in alphabetical order. goes to lower number to other locant.
Rule 5 Unsaturated branched acyclic hydrocarbons are named as derivatives of unbranched hydrocarbons which contain
maximum number of double and triple bonds.
2 2
1 1
CH3 3 CH3 3 CH3
5 3 CH2 4 CH2 6 4 CH2
6
HC 1 not HC or HC7
4 2 5 8 5 8
CH3 6 CH3 CH3
7
3,4-dipropyl-1,3-hexadien-5-yne
Carbon chain with maximum number of double/triple bonds is
selected as parent chain though it contains less no. of
carbon than other longer chain but with lower no. of
double/triple bonds, existing in the molecule.
Rule 6 If there are two or more chain competing for selection as the chain with maximum number of unsaturated bonds,
then the choice goes to
10 Essential Organic Chemistry
(ii) If the number of carbon atoms being equal, the one containing maximum number of double bonds is selected as the
parent chain.
7
CH CH
6
7 1 1
3 3
H2C CH2 not H2C CH2
5 5
6 4 2 4 2
5-ethynyl-1,3,6-heptatriene
1 1
3 CH2 5 3 CH2
4 2
not 6 4 2
5
6 CH2 CH2
4-ethynyl-1,5-hexadiene 4-vinyl-1-hexen-5-yne
CH2 CH2
H2C
H2C but
CH3 CH3
Isoprene 2,3-dimethyl-1,3-butadiene
not 3-methylisoprene
I II III
IV V
7 5
6 4
2 3 1
5 6 1
1 4 5
4
2 3
3 2
I II III
4-ethyl-5-methyl-2-hexene 2,5-dimethyl-3-heptene 3-propyl-1,4-pentadiene
(or 4-ethyl-5-methylhex-2-ene) (or 2,5-dimethylhept-3-ene)
6
5
7 5
3 6 1
3
6 4
2 3 1
5 6 2 1
1 4 5 3
3 4 2
I Nomenclature
II of Organic Compounds
III Chapter 1 11
4-ethyl-5-methyl-2-hexene 2,5-dimethyl-3-heptene 3-propyl-1,4-pentadiene
(or 4-ethyl-5-methylhex-2-ene) (or 2,5-dimethylhept-3-ene)
6
5
7 5
3 4 6 1
3
8 4 2
2
1
IV V
3-ethyl-2-methyl-4-propyl-1,5-hexadiene 3-ethyl-6-methyl-2,6-octadiene
I II III
IV V
1
2
4 2 4 2 3 5
5 3 1 5 3
1 4 6
7 6
I II III
4.4-dimethyl-1-pentyne 5-ethyl-5,6-dimethyl-2-heptyne 3-(1,2-dimethylpropyl)-1,5-hexadiyne
2 1
4
3 2
1 5
3
4
5
IV V
3-(1-ethylpropyl)-1,4-pentadiyne 3-butyl-3-propyl-1,4-pentadiyne
I II III
IV V
6 4 2 2 4 6
7
5 3 1
1
3 5
I II
5-hepten-1-yne 1-hexen-5-yne
(or Hept-5-en-1-yne) (or Hex-1-en-5-yne)
• Preference has gone to lower locant • Here both double bond and triple bonds are
number, not to triple bond. equidistant from terminals, hence alphabetical
• When ‘ene’ follow ‘yne’, ‘e’ of ene is order is followed in numbering the parent chain.
elided and written as enyne.
12 Essential Organic Chemistry
2 4 6 8 6 4 2 8 6 4 2
1 7 9 1 9 1
3 5 7 5 3 7 5 3
III IV V
1,3-heptadien-6-yne 3,8-nonadien-1-yne 8-nonene-1,3-diyne
(Here 'ene' is used because now
it follows consonent 'd')
I II III
IV V
Problem 1-9 Draw structures and write IUPAC name of all the alkenes with their molecular formula C5H10.
1-pentene 2-pentene 2-methyl-1-butene 3-methyl-1-butene 2-methyl-2-butene
Problem 1-10 Draw structures and write IUPAC name of all the alkynes with their molecular formula C5H8.
1-pentyne 2-pentyne 3-methyl-1-butyne
3
1 CH3 4 2 1
H3C H3 C
4 2 not
1 2
H3C CH3 4
H3C H3C 3
1,2,4-trimethylcyclohexene 4-ethyl-5-methylcyclohexene 5-ethyl-4-methylcyclohexene
CH3
1
2 3 2
5
3 1
Nomenclature of4Organic Compounds Chapter 1 13
Cyclohexene 1,3-cyclohexadiene 1,4-cyclohexadiene 1-cyclodecen-4-yne 3-methylcyclohexene
3
1 CH3 4 2 1
H3C H3 C
4 2 not
1 2
H3C CH3 4
H3C H3C 3
1,2,4-trimethylcyclohexene 4-ethyl-5-methylcyclohexene 5-ethyl-4-methylcyclohexene
If alkyl groups are equidistant from
double bond alphabetical order is
followed in numbering
CH3
1 4
2
H3C 5 3
4 3
H3C 2
CH3 1
1,3,5-trimethylcyclohexene 5-methyl-1,3-cyclohexadiene
not 2,4,6-trimethylcyclohexene
Rule 3 If a straight chain substituent attached to monocyclic hydrocarbon has greater number of carbon in the main
chain than the cyclic ring becomes substituent as
CH3 CH3 CH3
6
CH3 5
1
2 3 4 CH2
1 5 3
2 4
H3C
1-cyclopropyl-3-ethyl-2,4-dimethylhexane 1-cyclopentyl-3-ethyl-1,4-pentadiene
Problem 1-11 Write IUPAC names of the following substituted cyclic hydrocarbons
I II III IV V
I II
1-ethyl-3-isopropyl-5-methyl cyclohexane 1-cyclopropyl-3-methyl-5-propyl cyclohexane
1
6
3
3 1
III IV V
3-methylcycloheptene 1-ethyl-6-isopropyl-3-methyl cyclodecane Cyclopropylcyclopropane
14 Essential Organic Chemistry
Problem 1-12 Write IUPAC names of the following substituted cyclic hydrocarbons
I II III
IV V
2
1 3
4
5 1
4 5
2 7
3 6
I II
5-ethyl-1,2-dimethyl-1,3-cyclohexadiene 3,7-diethyl-1,4-cycloctadiene
2
1 1
4
3 2
III IV
1,4-dicyclohexylcyclohexene 1,2,3-tricyclopropylcyclopropane
2
4
1
V
4-cyclohexylcyclopentene
I II III IV
1
2 3
4
I II
2,3-dicyclopropyl-1,3-butadiene Cyclohexylethyne
2 3 2' 3
3'
2 1' 2'
1 4 1' 4
1
III IV
4-(3-cyclopropylcyclopentyl)cyclohexene 4-(2-cyclobutenyl)cyclohexene
Nomenclature of Organic Compounds Chapter 1 15
I II III IV
CH3
CH3
H2C CH3 CH3
CH3 CH3
CH3
4-ethylstyrene p-ethylstyrene 1,2-dimethyl-3-propylbenzene 1-butyl-3-ethyl-2-propylbenzene
16 Essential Organic Chemistry
I II III IV
4 4
2 2
1 1
I II
1,2,.4-trimethyl benzene 1,4-diisopropyl-2-propyl benzene
5
1
1 3
2 3
III IV
1,3-diethyl-2,5-dimethyl benzene 1-cyclohexyl-3-cyclopentyl benzene
If there is a choice between the two halides for numbering, alphabetical order is followed eg,
Br Br I
4
1
2 3 CH3 6 1 2 4 5 6
H3C 3 3 1
5
Cl 4
F F 2
Cl
2-bromo-3-chlorobutane 1-bromo-3fluorocyclohexane 1-chloro-3-fluoro-5-iodocyclohexane
1-3A Aldehydes
Acyclic mono- and dialdehydes are named by adding suffix “-al” or “-dial” to the name of acyclic hydrocarbon with the
same number of carbon atoms, eliding the final “e” of the hydrocarbon name before “a”. Numbering starts from the carbon
of the aldehyde group —CHO.
1 1
3 CHO 6 5 3 CHO
4 4 2
H3C 2 OHC
1
CH3CHO CHO H3C 5
7 6 H3C
Ethanal Pentanal 4-ethyl-2,5-heptadienal 2-ethylhexandial
If the parent chain contain more than two —CHO groups, they are named as carbaldehyde and carbon of —CHO is not
counted in main chain as
CHO CHO
1
4 4 2 6 5 CHO
CHO CHO
1 3
OHC 2 3 CHO OHC 4 2
3 1
1-3B Ketones
Ketones are named substitutively by adding a suffix such as “-one”, “-dione” etc to the name of parent hydrocarbon
O CH3 CH3 O
O CH3 7 5 4 1
C6H5 H3C 6 2 CH3
4 3
5 3 2 1
H3C CH3 O O
2-pentanone 1-phenylpentane-2,3-dione 4,6-dimethylhept-3-ene-2,5-dione