Nomenclature
of Organic
Compounds
Learning Framework
of the Chapter . . .
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.
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
Name
Name
Name
5
6
7
8
9
10
11
12
13
Pentane
Hexane
Heptane
Octane
Nonane
Decane
Undecane
Dodecane
Tridecane
14
15
16
17
18
19
20
21
22
Tetradecane
Pentadecane
Hexadecane
Heptadecane
Octadecane
Nonadecane
Icosane
Henicosane
Docosane
23
24
25
26
27
28
29
30
40
Tricosane
Tetracosane
Pentacosane
Hexacosane
Heptacosane
Octacosane
Nonacosane
Triacontane
Tetracontane
n
50
60
70
80
90
100
Name
Pentacontane
Hexacontane
Heptacontane
Octacontane
Nonacontane
Hectane
CH3CH2CH2CH2CH2CH3
n-hexane
H H H H H H
H HH
H
HCCCCCCCH
H3CCHCH2CH2CCH2CH3
H C H H C H H
CH3
2, 5, 5-trimethyl heptane
HH
HH
H
C
H
C
C
C
H
H
H
H
H H H H C H H
CH3
CH3
HCCCCCCH
H H H H H H
HH
C
H
HH
C
C
H
C
H
C
H HH
As shown in the above structures, carbon is tetravalent and associated with four covalent bonds (CH or CC bonds).
H
H
H
H H H H C H H
HCCCCCCCH=
H C H H C H H
H
HH
3CC bonds
ie, one H
4CC bonds
ie, no H
HH
2, 5, 5-trimethyl heptane
H
H
H
H
H
C
C
H
H
C
C
C
H
Cyclohexane
H H H
H =
H
HCCC == CH=
H C
HH
3-methyl-1-butene
CH3CH2CH2CH2Butyl
10
H3C(CH2)8CH2Decyl etc.
Rule 1 Selection of the longest carbon chain : The longest carbon chain gives parent name to the compound.
Rule 2 Numbering the longest chain : Longest chain is numbered starting from a terminal carbon. Numbering is done
in such a way that lowest possible number is given to the side chain as
H 3C
(1)
CH3
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
CH
CH3
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 (irrespective 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
6
H 3C
H 3C
CH3
CH3
3-methylheptane
H3C
8
7
CH3
6
CH3 CH3
CH3
2
CH3
CH3
CH3
2, 3, 5-trimethyl hexane
(not 2, 4, 5-trimethyl hexane)
H3C
CH3
7
H 3C
H3C
CH3
CH3
CH3
2
CH3
CH3
4-ethyl-2, 3, 6, 6, 8-pentamethyl-5-propylnonane
(not 6-ethyl-2, 4, 4, 7, 8-pentamethyl-5-propylnonane)
CH3
4-ethyl-7-propyldecane
(not 7-ethyl-4-propyldecane)
3-ethyl-7-methylnonane
(not 3-methyl-7-ethylnonane)
Rule 5 Following common names are retained in IUPAC system for unsubstituted hydrocarbons only
CH3
CH3
H3C
CH3
CH3 H3C
H3C
Isobutane
CH3
CH3
CH3
H3C
CH3
Isopentane
CH3
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
13
12
10
11
H3C
H3C
CH3
CH3 CH3
CH3
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
H3C
12
13
H3C
H3C
1
10
11
2
1
CH3
8
6
7
4
5
H3C
2
3
CH3
CH3
H3 C
6-(1-methylbutyl)-8-(2-methylbutyl) tridecane
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
CH3
CH3
4-isopropyl-5-propyloctane
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
H3C
H3 C
10
H3C
6 54
1
H3 C
H3C
3
CH3
3
CH3
CH3
CH3 1
5,5-bis(1, 1-dimethylpropyl)-2-methyldecane
13
H3C
10
12
11
9
1
H3C
CH3
6
CH3
H3 C
2
CH3
4 5
CH3
5,5-dimethyl-6-(1,1-dimethylbutyl)-6-pentyltridecane
H3C
CH3
H3C
H3C
CH3
H3 C
CH3
1
CH3
CH3
3
CH3
CH3
CH3
CH3
CH3
(Two locants)
(Wrongly numbered)
(b) The chain whose side chain has lowest numbered locants
CH3
6
H3C
CH3
3
H3C
CH3
1
CH3
H3C
CH3
5
CH3
H3C
CH3
1
CH3
H3 C
CH3
CH3
H3C
(Three locants)
(c) The chain having the greatest number of carbon atoms in the smaller side chain
H3C
H3C
H3C
13
H3 C
12
11
10
8 7
CH3 CH3
CH3
CH3
CH3
H3C
CH3
CH3
7,7-Bis(2,4-dimethylhexyl)-3-ethyl-5,9,11-trimethyltridecane
H3C
H3C
10
11
CH3
9
CH3
6-(1-isopropylpentyl)-5-propyldodecane
CH3
12
H3 C
H3C
11
10
3
8
4
7
CH3
5
CH3
CH3
Wrongly numbered
CH3
II
III
IV
V
2
4
3
II
5-ethyl-3,3-dimethyl heptane
3-ethyl-5-methylheptane
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.
4
2
1
10
6-ethyl-3,4-dimethyl octane
4
3
1
5
6
V
3,5-diethyl-2,3,5,6-tetramethyl heptane
Longest chain with maximum number of locants becomes the parent chain.
4-ethyl-2,2,6,6-tetramethyl heptane.
4-ethyl-2,3-dimethyl hexane.
6-ethyl-3-methyl-5-propyl nonane.
5-(1,2-dimethylpropyl)-5-(2,2-dimethylpropyl) nonane.
5-(1,2-dimethylpropyl)-6-(1-ethylpropyl) decane.
I
II
IV
1
2
IV
5-butyl-5-methyl-4-propyl decane
III
III
II
III
IV
3
2
9
8
6
5
1
I
5-(1-ethyl-2, 2-dimethylpropyl)-5
-(1, 2, 2-trimethylpropyl) nonane
10
1
6
10
9
III
11
10
9
II
5-(1, 1-dimethylpropyl)-6(2, 2-dimethylpropyl) decane
2
3
IV
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
2,4- dimethylpentane
2,3-dimethylpentane
3-methylhexane
3-ethylpentane
2,2-dimethylpentane
2,2,3,-trimethyl butane
4
3
3-heptene
6
5
CH3 H3C
7
4
3
6
5
2,4-heptadiene
CH3 H3C
7
7
6
3
4
1,3,5-octatriene
CH2
CH2==CH2 (Ethene)
CH2==C==CH2 (Allene)
Rule 2 Unsaturated, unbranched, acyclic hydrocarbons having one triple bond are named by replacing the ending -ane
of corresponding saturated hydrocarbon with the ending -yne. If there are two or more triple bonds, the ending will be
-adiyne, -atriyne etc. The chain is so numbered as to give lowest possible number to the triple bond.
2
HC
H3C
CH3
CH3
Pentyne
(Its triple bond is at terminal positions,
therefore, it need not numbered)
H3C
2-hexyne
CH3
2
2,4,6-octatriyne
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
H2C
CH
HC
CH3
3-penten -1-yne
1,3-hexadien-5-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).
4
HC
CH2
H3 C
5
6
CH3
CH3
1-penten-4-yne
Here both double bond and triple bonds are
equidistant from terminals hence, numbering is
done in alphabetical order.
4-methyl-6-octen-2-yne
Here both double bond and triple bonds are
equidistant from terminals hence, preference
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
6
HC
3
4
CH3
CH2
1
CH3
not HC
CH3
CH3
CH2
or HC7
4
5
CH3
CH2
3
8
CH3
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
CH2
8
H3C
3
4
CH2
H3C
5-vinyl-1,3,5-octatriene
CH2
4
CH2
(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
7
H2C
3
4
CH2
CH
H2C
not
CH2
5-ethynyl-1,3,6-heptatriene
1
3
4
5
CH2
not
6 CH2
CH2
CH2
4-ethynyl-1,5-hexadiene
4-vinyl-1-hexen-5-yne
H2C
but
CH3
CH2
H2C
CH3
Isoprene
2,3-dimethyl-1,3-butadiene
not 3-methylisoprene
II
III
IV
2
1
7
3
4
I
II
4-ethyl-5-methyl-2-hexene
2,5-dimethyl-3-heptene
(or 4-ethyl-5-methylhex-2-ene) (or 2,5-dimethylhept-3-ene)
5
3
III
3-propyl-1,4-pentadiene
6
7
1
2
2
1
Nomenclature
of Organic Compounds
Chapter 1 11
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
3 4
1
1
2
IV
V
3-ethyl-2-methyl-4-propyl-1,5-hexadiene 3-ethyl-6-methyl-2,6-octadiene
II
III
IV
V
1
4
5
II
5-ethyl-5,6-dimethyl-2-heptyne
2
III
3-(1,2-dimethylpropyl)-1,5-hexadiyne
3
4
5
IV
3-(1-ethylpropyl)-1,4-pentadiyne
V
3-butyl-3-propyl-1,4-pentadiyne
II
III
IV
6
7
4
3
I
5-hepten-1-yne
(or Hept-5-en-1-yne)
I
4.4-dimethyl-1-pentyne
3
1
2
1
4
3
6
5
II
1-hexen-5-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.
4
3
6
5
III
1,3-heptadien-6-yne
8
1
6
7
2
3
V
8-nonene-1,3-diyne
(Here 'ene' is used because now
it follows consonent 'd')
IV
3,8-nonadien-1-yne
(II) 3,4-diethyl-1,4-hexadiene.
(IV) 4-ethenyl-3-ethyl-1,6-octadiene.
I
II
III
IV
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
Cyclopropane Cyclopentane
Cyclohexane
Cyclo-octane
Rule 2 Name of unsaturated monocyclic hydrocarbons (with no side groups) is formed by substituting -ene, -yne,
-adiene, -atriene, -adiyne etc for ane in the name of corresponding cycloalkane eg,
1
5
Cyclohexene
1,3-cyclohexadiene
1
H3C
CH3
CH3
1,2,4-trimethylcyclohexene
H3C
H3C
1-cyclodecen-4-yne
3
2
1
4-ethyl-5-methylcyclohexene
2
3
1,4-cyclohexadiene
CH3
not
2
1
3-methylcyclohexene
1
H3 C
H3C
5-ethyl-4-methylcyclohexene
CH3
Cyclohexene
H3C
2
1
1,3-cyclohexadiene
1
1,4-cyclohexadiene
CH3
H3C
CH3
1-cyclodecen-4-yne
H3 C
not
H3C
1,2,4-trimethylcyclohexene
3-methylcyclohexene
H3C
4-ethyl-5-methylcyclohexene
5-ethyl-4-methylcyclohexene
CH3
H3C
H3C 5
CH3
1,3,5-trimethylcyclohexene
not 2,4,6-trimethylcyclohexene
3
2
5-methyl-1,3-cyclohexadiene
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
1
2 3 4
CH3
CH3
1
2
H3C
1-cyclopropyl-3-ethyl-2,4-dimethylhexane
CH2
1-cyclopentyl-3-ethyl-1,4-pentadiene
Problem 1-11 Write IUPAC names of the following substituted cyclic hydrocarbons
II
III
IV
3-methylcycloheptene
1-cyclopropyl-3-methyl-5-propyl cyclohexane
III
II
1-ethyl-3-isopropyl-5-methyl cyclohexane
3
1
IV
1-ethyl-6-isopropyl-3-methyl cyclodecane
V
Cyclopropylcyclopropane
II
III
IV
V
2
5
4
3
1
7
4
5
6
II
5-ethyl-1,2-dimethyl-1,3-cyclohexadiene
3,7-diethyl-1,4-cycloctadiene
2
1
III
IV
1,4-dicyclohexylcyclohexene
1,2,3-tricyclopropylcyclopropane
2
1
4-cyclohexylcyclopentene
II
III
IV
II
2,3-dicyclopropyl-1,3-butadiene
2
1
2'
1'
Cyclohexylethyne
3'
3
2
1'
2'
III
4-(3-cyclopropylcyclopentyl)cyclohexene
IV
4-(2-cyclobutenyl)cyclohexene
(II) 4-ethyl-6-methylcycloheptene
(IV) 1,4-dicyclopentylcyclopentene
I
II
III
IV
CH3
Benzene
Cumene
CH3
CH3
Toluene
Styrene
CH3
CH3
CH3
o-xylene
m-xylene
CH3
H3C
CH3
p-xylene
H3C
CH3
Mesitylene
CH3
Cymene
Rule 1 Other monocyclic substituted hydrocarbons are named as derivatives of benzene or one of the compounds listed
above. However, if the substituent introduced into such a compound is identical with already present in that compound, then
the substituted compound is named as derivatives of benzene as
CH3
H2C
CH3
1,4-divinylbenzene
CH2
CH2
CH3
1-methyl-3-vinylbenzene
1,2,3-trimethylbenzene
Rule 2 The positions of substituents is indicated by numbers except o-(ortho), m-(meta), p-(para) may be used in place
of 1,2- , 1,3- , and 1,4-, respectively, when only two substituents are present. The lowest possible number given to the substituent coming 1st in alphabetical order except that when names are based on those of the compounds mentioned in the beginning
of section-E.
CH3
H3C
CH3
1-ethyl-4-pentylbenzene
H3C
1,4-dipropylbenzene
CH3
CH3
H2C
CH3
CH3
4-ethylstyrene p-ethylstyrene
CH3
1,2-dimethyl-3-propylbenzene
H3C
CH3
3,5-diethyltoluene
CH3
CH3
CH3
1-butyl-3-ethyl-2-propylbenzene
II
III
IV
4
4
2
2
1
II
1,2,.4-trimethyl benzene
1,4-diisopropyl-2-propyl benzene
III
IV
1,3-diethyl-2,5-dimethyl benzene
1-cyclohexyl-3-cyclopentyl benzene
Cl
6
H3C
CH3
Cl
9
H3C
5 4
Cl
3-chlorohexane
Cl
CH3
H3C
Cl
5 4
CH3
Br
3,4,7-trichlorononane
5-bromo-2-chloroctane
If there is a choice between the two halides for numbering, alphabetical order is followed eg,
Br
Br
1
H3C
CH3
Cl
2-bromo-3-chlorobutane
2
3
5
4
1-bromo-3fluorocyclohexane
5
3
6
1
Cl
1-chloro-3-fluoro-5-iodocyclohexane
Formula
Prefix
Suffix
COX
OH
Halocarbonyl
Hydroxy
Carbonyl halide
(3) Aldehydes
CHO
(C)HO
Formyl
Oxo-
(4) Amides
CONH2
(C)ONH2
Carbaldehyde
-al
Carbamoyl
Carboxamide
-amide
-amine
-ol
NH2
COOH
(C)OOH
OR
Amine
Carboxy
(8) Esters
COOR
(C)OOR
R-oxycarbonyl
R-carboxylate
R-oate
(9) Ketones
(C)==O
CN
(C)N
SO3H
Oxo
-one
Cyano
-carbonitrile
nitrile
Sulpho
-Sulphonic acid
(5) Amines
(6) Carboxylic acid
(7) Ethers
(10) Nitrile
(11) Sulphonic acid
-carboxylic acid
-oic acid
Alkoxy
(Formulae containing carbon in parenthesis indicates that the carbon is part of main chain)
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.
H3C
CH3CHO
CHO
Ethanal
Pentanal
H3C
CHO
OHC
CHO
H3C
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
4
OHC
CHO
Butane-1,2,4-tricarbaldehyde
CHO
CHO
Cyclohexanecarbaldehyde
OHC
5
4
CHO
2
3-(formylmethyl) hexanedial
or 3-(2-oxoethyl) hexanedial
4-cyclopentylbutanal
1-3B Ketones
Ketones are named substitutively by adding a suffix such as -one, -dione etc to the name of parent hydrocarbon
CH3 CH3 O
O
O
5
H3C
3 2
2-pentanone
CH3
CH3
C6H5
O
1-phenylpentane-2,3-dione
H3C
5 4
CH3
O
4,6-dimethylhept-3-ene-2,5-dione