IUPAC rules for the nomenclature of unsaturated hydrocarbons

(alkenes and alkynes)

1) Selection of parent chain: The longest possible continuous chain of

carbon atoms in the organic compound that includes carbon-carbon double
bond or triple bond is selected as parent chain. If the compound contains
many carbon–carbon double bonds and triple bonds, the carbon chain
having maximum no. of carbon-carbon multiple bonds should be selected as
parent chain. CH2 CH2

H3C CH2 CH2 C CH2 CH3 H3C CH2 CH2 C CH2 CH3

No of C-atoms in the chain: 5 (shorter) No of C-atoms in the chain: 6 (longer)

The selected chain includes The selected chain does not include
Carbon-carbon double bond Carbon-carbon double bond (wrong)
IUPAC name: 2-ethylpent-1-ene
2) Lowest locant no. rule: If only one carbon-carbon double or triple bond is
present in the organic compound, the locant no. is given from one end of the
parent chain in such a way that the carbon atoms containing double bond or triple
bond gets the lowest possible locant number.

CH2CH3 CH2CH3
3
4 6 4 2 1
1 2 3 H2 5 6 5 H2
H3C CH2 CH C C CH2 H3C CH2 CH C C CH2
H H
Locant no. of double bond: 1
Locant no. of double bond: 5 (Lowest: correct)
(highest: wrong) Pref ix: ethyl
Word root: hex
Primary suf f ix: ene
CH3-CH2-CH2-CH=CH2 Secondary suf f ux: -
CH3 IUPAC Name: 4-ethylhex-1-ene Or 4-ethylhexene-1
3) Lowest set of locant no. rule: If two or more carbon-carbon double or triple
bonds (multiple bonds) are present in the organic compound, the locant no. is given
from one end of the parent chain so as to get the lowest possible set of locant
numbers. The locant no. should be written in increasing order. The first locant no. of
each possible set is compared. The set of locant no. which is lower is selected. If first
locants are same, the next locants are compared and soon. While writing diene (for
two carbon-carbon double bonds) diyne (for two triple bonds), triene, triyne etc, the
letter ‘a’ must be written after word root and before the primary suffixes)
4
2 5 H 3 2 1
1 H 3 4 5 H3C C CH C CH2
H3C C CH C CH2 H
H
Set of locant no. f or double bond: [1,3]
Set of locant no. f or double bond: [2,4] (lowest: correct)
(largest: wrong) Pref ix: -
Word root: pent
Primary suf f ix: diene
Secondary suf f ix: -
IUPAC name: Penta-1,3-diene OR 1,3-Pentadiene
 1 2 4 5 6 6 5 4 3 2 1
3 HC C CH2 C C CH3
HC C CH2 C C CH3

Set of locant no. f or double bond: [1,4] Set of locant no. f or double bond: [2,5]
(lowest: correct) (largest: wrong)
Pref ix: -
Word root: hex
Primary suf f ix: diyne
Secondary suf f ix: -
IUPAC name: Hexa-1,4-diyne

Q. CH2=CH-CH2-CH=CH2
CH3
Answer: 2-methylpenta-1,4-diene
4) If carbon-carbon double bond and triple bonds are present together,
a) the parent chain that includes maximum number of carbon to carbon, multiple bonds
is selected.

b) the carbon atoms in the parent chain are numbered by the lowest set of locant
number rule.

c) the primary suffix ‘ene’ for carbon-carbon double bond is written before the primary
suffix ’yne’ for carbon-carbon triple bonds dropping ‘e’ of -ene.

1 2 H 3 4 5 5 4H 3 2 1
H3C C CH C CH H3C C CH C CH

Set of locant no.: [2,4] (highest: wrong) Set of locant no.: [1,3] (Lowest: correct)
Pref ix: -
Word root: pent
Q. CH3-C≡C-CH=CH-CH=CH2 Primary suf f ix: ene, yne
Secondary suf f ix: -
Answer: Hepta-1,3-dien-5-yne IUPAC name: Pent-3-en-1-yne OR 3-Pentenyne-1
structure IUPAC name Common name

H2C=CH2 Ethene Ethylene

CH3-CH=CH2 Prop-1-ene propylene

CH3-CH2-CH=CH2 (C4H8) But-1-ene α- butylene

CH3-CH=CH-CH3 (C4H8) But-2-ene β- butylene

CH3-C=CH2 2-Methylprop-1-ene isobutylene

CH3
Structure IUPAC NAME Common name

HC≡CH Ethyne Acetylene

CH3-C≡CH Prop-1-yne Methyl acetylene

CH3-CH2-C≡CH But-1-yne Ethyl acetylene

CH3-C≡C-CH3 But-2-yne Dimethyl acetylene

Homework

I I
Cl
 Nomenclature of organic compounds having functional groups
1) Longest chain rule: The longest possible continuous chain of carbon atoms
including the carbon atoms of functional group such as –COOH, -CONH2 ,
-COCl, -CN, -CHO etc. and all those which carry the functional groups such as –
OH, -NH2 , -NO2 , -X (F, Cl, Br, I) etc. is selected as the parent chain. The no. of
carbon atoms in the parent chain determines the word root.
5 6 7 H2
CH2 CH2 CH3 CH2 C CH3

2 3 H2
4 H3C CH2 CH CH2 CH C CH3
H3C CH2 CH CH2 CH CH2 CH3

CH2OH CH2OH
1
The selected chain includes f unctional group (Correct) The selected chain does not include f unctional group (wrong)
Pref ix: diethyl
Word root: hept
Primary suf f ix: ane
Secondary suf f ix:ol
IUPAC name: 2,4-diethylheptan-1-ol Q. What is longest chain rule?
2) Lowest locant number rule:
a) If the functional group having carbon atom such as –COOH, -CONH2 , -COCl,
-CN, -CHO etc is present in the parent chain, the carbon atoms of the parent chain
are numbered in such a way that the carbon atom of functional group gets the locant
number of 1. The locant no. 1 is not written for these functional groups as they always
come at the end having locant no. of 1.
6 7 2 1
CH2 CH3 CH2 CH3

5 4 3 2 1 3 4 5 6 7
H3C CH CH2 CH2 CH2 COOH H3C CH CH2 CH2 CH2 COOH

Locant no. of f unctional group: 1 (lowest) (correct) Locant no. of f unctional group: 7 (highest) (wrong)
Pref ix: methyl
Word root: hept
Primary suf f ix: ane
Secondary suf f ix: oic acid
IUPAC name: 5-methylheptanoic acid
b) If the functional group does not have the carbon atom, then the carbon atom
of the parent chain bonded to the functional group should get the lowest
possible locant number.

CH3 OH
CH3 OH
4 1 2 3 4 5
5 3 2 1 H3C CH CH2 CH CH3
H3C CH CH2 CH CH3

Locant no. of f unctional group: 2 (lowest) (correct) Locant no. of f unctional group: 4 (highest: wrong)
Pref ix: methyl
Word root: pent
Primary suf f ix: ane
Secondary suf f ix: ol
IUPAC name: 4-methylpentan-2-ol
c) If the parent chain contains multiple bonds ( carbon-carbon double or triple
bonds), the carbon atom of parent chain are counted from one end so as to give the
lowest possible locant no. to the carbon atom joining double or triple bond. However,
if functional group is present in addition to the multiple bond, the carbon atom of the
functional group or carbon atom carrying functional group should get the lowest
possible locant number.
OH OH
1 2 3 4 5 6 6 5 4 3 2 1
H3C CH CH2 CH2 C CH2 H3C CH CH2 CH2 C CH2
H H

Locant no. of f unctional group: 2 (lowest) (correct) Locant no. of f unctional group: 5 (highest: wrong)
Pref ix: -
Word root: hex
Primary suf f ix: ene
Secondary suf f ix: ol
IUPAC name: Hex-5-en-2-ol
3) Lowest set of locant no. rule: If the parent chain contains more than one
similar functional groups, the no. of carbon atoms in the parent chain are counted in
such a way that the lowest set of locant numbers is obtained at first point of
difference and so on. The numerical prefixes such as di (for two), tri (for three), tetra
(for four) etc. are added before the secondary suffix which indicates the functional
group. While adding such words, the vowel ‘e’ of the primary suffix is retained.
OH OH OH OH
4 3 2 1 1 2 3 4
H3C CH CH CH2 OH H3C CH CH CH2 OH
Set of locant no.: [1,2,3] (Lowest: correct) set of locant no.: [2,3,4] (highest: wrong)
Pref ix: -
Word root: but
Primary suf f ix: ane
Secondary suf f ix: - triol
IUPAC name: Butane-1,2,3-triol