IUPAC Nomenclature and

01 Common Names
History :
In 1675, Nicholas Lemery divided chemical substances into 3 parts.
(i) Mineral substance : which are obtained from minerals. eg. gold, silver, iron etc.
(ii) Vegetable substance : which are obtained from vegetables. eg. sugar, citric acid etc.
(iii) Animal substance : which are obtained from animals. eg. albumin, gilatin etc.
After some time when many of the chemical substance were discovered, it was found that some of them
can be obtained from both vegetables and animals. So this classification was failed. So chemical
substance were then divided into two parts :
(i) Organic compounds : which are obtained from living organism.
(ii) Inorganic compounds : compounds which are obtained from any other sources except living
organisms.

VFT(Vital Force Theory) : By Berzelius in 1815. Upto 1815, any organic compound could not be
synthesized in lab. So Berzelius suggested that there is a mysterious force in living organisms which was
named as Vital Force and said that organic compounds cannot be synthesized in lab. This theory was called
as VFT.
But in 1828 a German scientist Wholar synthesized an organic compound in lab. Which was 'urea'. So VFT
was failed. Urea was synthesized in lab by heating of Ammonium cyanate (NH4CNO).

NH4CNO Rearrangement NH2—C—NH2
Ammonium cyanate
O
Urea

Organic Compounds : Hydrocarbons and their derivatives are called as organic compounds.

Characteristics of C-Atoms :
(a) Tetra valency : Atomic number of carbon atom is 6 and it have four valency electrons so C-Atom is
tetravalent. It is explained by promotion rule
In ground state (here covalency of carbon is 2)
First excited state (here covalency of carbon is 4)
2s 2p

Available for bond formation

(b) Tendency to form multiple bonds : Carbon atom forms following type of bonds, such as

―C―C―, ―C = C―, ―C  C―, ―C = C = C―

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(c) Tetrahedral shape : The four covalent bond are directed
towards the four corners of a regular tetrahedron
Bond angle 10928' or 109.5'

C 109°28'

(d) Catenation : Carbon atoms have the tendency to link with one another through covalent bonds to form
chains and rings. This property is called catenation. This is because C—C bonds are very strong. Down
the group the size increases and electronegativity decreases, and, thereby, tendency to show catenation
decreases. This can be clearly seen from bond enthalpies values. The order of catenation is C > > Si >
Ge  Sn. Lead does not show catenation.
Due to property of catenation and p– p bond formation, carbon is able to show allotropic forms.

Bond Bond enthalpy / kJ mol–1

C—C 348
Si—Si 297
Ge—Ge 260
Sn—Sn 240

(e) Hybridisation : The orbitals of different shape but almost of equal energies blend up to give the same
number of new orbitals of another shape and of identical energies.
Structure  &  bonds Hybridisation Bond angle Shape

C 4,0 sp3 109°28' Tetrahedral

C 3,1 sp2 120° Planar (Trigonal)

C 2,2 sp 180° Linear

C 2,2 sp 180° Linear

Structural representations of organic compounds :

Complete, Condensed and Bond-line Structural Formulas of organic compounds are represented in several
ways. The Lewis structure or dot structure, dash structure, condensed structure and bond line structural
formulas are some of the specific types. The Lewis structures, however, can be simplified by representing
the two-electron covalent bond by a dash (–). Such a structural formula focuses on the electrons involved
in bond formation. A single dash represents a single bond, double dash is used for double bond and a triple
dash represents triple bond. Lone-pairs of electrons on heteroatoms (e.g., oxygen, nitrogen, sulphur,
halogens etc.) may or may not be shown. Thus, ethane (C2H6), ethene (C2H4), ethyne (C2H2) and methanol
(CH3OH) can be represented by the following structural formulas. Such structural representations are
called complete structural formulas.
H H
H H
CH3 H
H—C—C—H C C H—CC—H H—C—O—H or H—C—O—H
CH3 H
H H H H
Ethane Ethene Ethyne Methanol

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IUPAC Nomenclature and Common Names
These structural formulas can be further abbreviated by omitting some or all of the dashes representing
covalent bonds and by indicating the number of identical groups attached to an atom by a subscript. The
resulting expression of the compound is called a condensed structural formula. Thus, ethane, ethene,
ethyne and methanol can be written as:
CH3CH3 H2C=CH2 HC≡CH CH3OH
Ethane Ethene Ethyne Methanol

Similarly, CH3CH2CH2CH2CH2CH2CH2CH3 can be further condensed to CH3(CH2)6CH3. For further

simplification, organic chemists use another way of representing the structures, in which only lines are
used. In this bond-line structural representation of organic compounds, carbon and hydrogen atoms are
not shown and the lines representing carbon-carbon bonds are drawn in a zig-zag fashion. The only atoms
specifically written are oxygen, chlorine, nitrogen etc. The terminals denote methyl (–CH3) groups (unless
indicated otherwise by a functional group), while the line junctions denote carbon atoms bonded to
appropriate number of hydrogens required to satisfy the valency of the carbon atoms. Some of the
examples are represented as follows:
(i) 3-Methyloctane can be represented in various forms as:
CH2 CH2 CH2 CH3
(a) CH3CH2CHCH2CH2CH2CH2C (b) CH3 CH CH2 CH2
H3
CH3 CH3

(c)

Terminals represent.
methyl group
(ii) Various ways of representing 2-bromo butane are:
CH3 CH2
(a) CH3CHBrCH2CH3 (b) CH CH3 (c)
Br
Br
In cyclic compounds, the bond-line formulas may be given as follows:
CH2 CH2
CH2 CI
H2C CHCI
H2C CH2
H2C CH2
H2C CH2 H2C CH2 CH2
Cyclopropane
Cyclopentane Chlorocyclohexane

Illustration 1:
Expand each of the following condensed formulas into their complete structural formulas.
(a) CH3CH2COCH2CH3 (b) CH3CH=CH(CH2)3CH3
Solution:
H H O H H H H H H H H

(a) H—C—C—C—C—C—H (b) H—C—C==C—C—C—C—C—H

H H H H H H H H H H

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Illustration 2 :
For each of the following compounds, write a condensed formula and also their bond-line formula.
OH
(a) HOCH2CH2CH2CH(CH3)CH(CH3)CH3 (b) N C—CH—C N
Solution:
Condensed formula:
(a) HO(CH2)3CH(CH3)CH(CH3)2
(b) HOCH(CN)2
Bond-line formula:
OH
(a) HO (b)
NC CN
Illustration 3:
Expand each of the following bond-line formulas to show all the atoms including carbon and hydrogen

(a) (b) (c) (d)

OH
Solution:
H HH H
C C H H H H H H H H
H H CH3
(a) C C (b) H—C—C—C—C—C—C—C—C—H
H C H
C C CH3 H H H H H H H H
H H H H
H H H CH3
H3C
(c) H—C C—C—C—C—H (d) HH—C—C—H
H3C CH3
H OH H
H
 - (sigma) bonds : The molecular orbital formed by the overlapping of two-s atomic orbitals or one s and
one p atomic orbitals or co-axial overlapping of p-orbitals is called a  bond.
Note :
(i) Overlapping of hybrid orbitals also give  bonds.  bonds are stronger, as they are resulted from the
effective axial overlapping.
(ii) More the directional character (p) in covalent bond more is the strength of the bond.
sp3 - sp3 > sp3 - sp2 > sp2 - sp2 > sp – sp
(Pi) bonds :  bond is formed by the lateral overlapping of two p-atomic orbitals. It is weaker than 
bond, as there is only partial overlapping.
sp sp sp2 sp2 sp3
Ex. HC C—CH CH—CH3
H

C
H C C  H
Ex. 120 Flat hexagonal structure due to sp2 hybridised C-atom in benzene
H C ° C  H
C

H

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IUPAC Nomenclature and Common Names

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Classification of organic compounds :
Aliphatic or open chain compounds :
Those compounds in which first & last carbon atoms are not connected with each other. Branched or
unbranched chains are possible in these compounds.
For example :
CH3
CH3–CH2–CH2–CH3 , CH3–CH2–CH–CH3 , CH3—C—CH3
CH3 CH3
(Unbranched) (Branched)
There are two varieties in these compounds –

Saturated hydrocarbons :
(a) In such type, adjacent carbon are attached with single bonds.
Example - CH3–CH2–CH3
(b) General formula of these compounds are CnH2n+2
(c) These are also called as paraffins (Parum + Affins i.e. little reactivity) because these are less
reactive due to absence of -bonds.

Unsaturated hydrocarbons :
(a) There will be a double bond or a triple bond between any two carbon atoms,
CH2 = CH – CH3 Propene
CH  C – CH3 Propyne
(b) General formula is CnH2n or Cn H2n–2
(c) These are also called as olefins because they reacts with halogens to form oily substances
olefins (Oleum + fines i.e. Oil forming).
(d) Due to presence of  bonds these are more reactive.

Closed chain compounds :

In these compounds first & last carbon are attached with each other.
CH2

Example CH2—CH2 cyclopropane.

Homocyclic compounds :
These are the compounds in which the complete ring is formed by carbon atoms only. These are also of
two types
(A) Alicyclic compounds : These are the compounds having the properties like aliphatic compounds.
These may be saturated or unsaturated like aliphatic compounds.

cyclopropane cyclopropene cyclobutene

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IUPAC Nomenclature and Common Names
(B) Aromatic compounds : Conditions for a compound to be aromatic -
(i) Compound should be cyclic.
(ii) Compound should be planar. (All carbon in ring should be sp2 hybridised)
(iii) It follow Huckel's Rule :- [4n + 2]  electrons. (Odd number of  electron pairs)
n=0 2 electrons or 1 pair
n=1 6 electrons or 3 pairs
n=2 10 electrons or 5 pairs
n=3 14 electrons or 7 pairs
(iv) There should be cyclic resonance in ring.

Heterocyclic compounds :
These are cyclic compounds having ring and rings build up of more than one kind of atoms.

N
O S
H
Furan Thiophene Pyrrole

Homologous Series :
A group or a series of organic compounds each containing a characteristic functional group forms a
homologous series and the members of the series are called homologues. The members of a homologous
series can be represented by general molecular formula and the successive members differ from each other
in molecular formula by a –CH2 unit. There are a number of homologous series of organic compounds. Some
of these are alkanes, alkenes, alkynes, haloalkanes, alkanols, alkanals, alkanones, alkanoic acids, amines
etc. It is also possible that a compound contains two or more identical or different functional groups. This
gives rise to polyfunctional compounds.

Groups :
Normal groups :
(a) It is represented by 'n' :
(b) Straight chain of carbon atoms is known as normal group.
(c) Free bond will come either on Ist carbon atom or on last carbon atom.
n–propyl CH3–CH2–CH2–
n–butylCH3–CH2–CH2–CH2–

Iso group :
(a) It is represented by following structure
CH3–CH–
CH3
(b) When methyl groups are attached to the second last carbon atom, group is named as iso.
CH3–CH– CH3–CH–CH2– CH3–CH–CH2–CH2–
CH3 CH3 CH3
Iso propyl Iso butyl Isopentyl

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Neo group :
(a) When two methyl group are attached to second last carbon atom group is named neo group.
(b) It is represent by following structure -
CH3
for Ex. CH3–C–CH2– Neo pentyl
CH3

Secondary group :
(a) When two alkyl groups attached to the same carbon atom, group is named as secondary.
Ex.
CH3–CH2–CH– CH3–CH2–CH2–CH–
CH3 CH3
Secondary butyl Active Secondary pentyl
(b) It is represented by following structure.
CH3–CH2–CH–CH3

CH3
Tertiary group :
(a) When three alkyl groups (similar or dissimilar) are attached to the same carbon atom, group is name
as tertiary.
CH3 CH3
CH3–C– CH3–CH2–C–
CH3 CH3
Tertiary butyl Tertiary pentyl

(b) It is represented by following structure -

CH3
CH3–C–
CH3

Alkyl groups :
When a hydrogen is removed from saturated hydrocarbon then alkyl group is formed. It is represented by
R & its general formula is CnH2n+1. A bond is vacant on alkyl group, on which any functional group may
come.
–H –H –H
Alkane Alkyl (monovalent radical) Bivalent radical Trivalent radical
CH4 → –CH3 Methyl C2H6 → –C2H5 Ethyl
Methyl
CH3–CH2–CH3 (i) CH3–CH2–CH2– n-propyl
Propane
(ii) CH3–CH–CH3 Iso-propyl

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IUPAC Nomenclature and Common Names
CH3–CH2–CH2–CH3 (i) CH3–CH2–CH2–CH2– n-butyl
Butane
(ii) CH3–CH2–CH–CH3 sec-butyl

CH3–CH–CH3 (i) CH3–CH–CH2– Isobutyl

CH3 CH3
Isobutane
(ii) CH3–C–CH3 tert. butyl
CH3
(a) CH3–CH2–CH2–CH2–CH2– n-pentyl

CH3CH2CH2CH2CH3 (b) CH3–CH2–CH2–CH–CH3 Active sec. pentyl

n–Pentane
(c) CH3–CH2–CH–CH2–CH3 1-Ethyl propyl
or sec. pentyl
(a) CH3–CH–CH2–CH2– Iso Pentyl or
3-Methyl butyl
CH3

CH3–CH–CH2–CH3 1,2-dimethyl propyl

(b) CH3–CH–CH–CH3
or active iso pentyl
CH3 CH3
Iso pentane
(c) CH3–C–CH2–CH3 tert. pentyl or
1, 1-dimethyl propyl
CH3 or tert. amyl

(d) CH2–CH–CH2–CH3 Active pentyl or

active amyl
CH3
CH CH
3
CH3–C–CH3 ⎯⎯→ CH3–C–CH2–
CH CH
neo-pentane
3 neo-pentyl

Note 1 : Pentyl is also called amyl group.

Note 2 : (Optically active) if all valency are attached to different atoms.
−H
(a) Alkene ⎯⎯⎯ → Alkenyl
Ex. CH2=CH2 ⎯⎯
→ CH2=CH– Ethenyl (vinyl)
CH3–CH=CH2 ⎯⎯
→ (1) CH3–CH=CH– 1–propenyl

(2) CH3–C=CH2 Iso propenyl or

1–methyl ethenyl
(3) –CH2–CH=CH2 2–Propenyl (Allyl)

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−H
(b) Alkyne ⎯⎯ → Alkynyl
Ex.
CH CH CH C— Ethynyl

CH3–C CH CH3–C C— 1–Propynyl

–CH2–C CH 2–Propynyl
(Propargyl)
Aryl radical :

(i) –H –H
–C6H5

Phene Phenyl Phenylene (–C6H4)

CH2 CH C—

CH3 –H –H

(ii)
Benzyl Benzal or Benzo(Benzylidyne)
Benzyliden
Toluene e

CH3 CH3 CH3

o–Tollyl m–Tollyl p–Tollyl

CH2OH CHO COOH

Ex. Benzyl alcohol Benzaldehyde Benzoic acid

IUPAC system of Nomenclature :

The IUPAC system is the most widely used system of nomenclature in organic chemistry. The most
important feature of this system is that any given molecular structure has only one IUPAC name and any
given IUPAC name denotes only one molecular structure.
The IUPAC name of organic compound may consists of five parts, i.e.
1. Word root
2. Primary Suffix
3. Secondary Suffix
4. Primary Prefix
5. Secondary Prefix

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IUPAC Nomenclature and Common Names
A complete IUPAC name of an organic compound have the following sequence :
Secondary prefix +Primary prefix + Word root + Primary suffix + Secondary suffix
1. Word root : It is the basic unit of the name. It denotes the number of carbon atoms present in the
principal chain (the longest possible continuous chain of carbon atoms including the functional group
and based upon the common names of alkanes) of the organic molecules.
Root word : According to number of carbon's in parent C–chain.
Number of carbons Root word Number of carbons Root word
1 Meth 8 Oct
2 Eth 9 Non
3 Prop 10 Dec
4 But 11 Undec
5 Pent 12 Dodec
6 Hex 13 Tridec
7 Hept

2. Primary suffix : A primary suffix is always added to the root word to indicate whether the carbon
chain is saturated or unsaturated. The three basic primary suffixes are given below :
S. No. Type of carbon chain Primary Suffix General Name

1 (a) Saturated -ane Alkane

2 (b) Unsaturated with one double bond -ene Alkene

3 (c) Unsaturated with one triple bond -yne Alkyne

If the parent carbon chain contain two, three or more double or triple bond, numerical prefix such as
di (for two), tri (for three), tetra (for four) etc. are added to the primary suffix. For example.

S. No. Type of carbon chain Primary Suffix General Name

1 (a) Unsaturated with two double bonds -diene Alkadiene

2 (b) Unsaturated with two triple bonds -diyne Alkadiyne

3. Secondary suffix : A secondary suffix is always added to the primary suffix to indicate the nature
of the functional group present in the organic compounds. Secondary suffix of some important
functional groups are given below.

S. No. Class of organic compounds Functional group Secondary Suffix

1 Alcohols – OH - ol
2 Aldehydes –CHO - al
3 Ketones >C=O - one
4 Carboxylic acids – COOH - oic acid
5 Acid amides –CONH2 - amide

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6 Acid chlorides – COX - oyl halide
7 Esters – COOR alkanoate
8 Nitriles – CN - nitrile
9 Thioalcohols – SH - thiol
10 Amines – NH2 - amine
The following examples illustrate the use of word root, primary suffix and secondary suffix in naming of
organic compounds.
Organic Primary Secondary
S. No. Word root IUPAC name
Compounds suffix suffix
1 CH3CH2OH Eth an (e) ol Ethanol
2 CH3CH2CH2NH2 Prop an (e) Amine Propanamine
3 CH3CH2CH2COOH But an (e) oic acid Butanoic acid
4 CH3CH2CN Prop an(e) nitrile Propanenitrile
5 CH2 = CHCHO Prop en(e) al Propenal
6 HC  CCOOH Prop yn(e) oic acid Propynoic acid

4. Primary prefix : A primary prefix is used simply to distinguish cyclic from acyclic compounds. For
example, in case of carbocyclic compounds.(cyclic compounds containing only carbon atoms in the
ring.), a primary prefix, cyclo is used immediately before the word root. Thus.
CH2
eg. : CH2 CH2 Cyclo + Pent + ane = Cyclopentan
e
CH2 CH2 Primary + Word + Primary = IUPA
prefix root suffix C
If the prefix cyclo is not used, it simply indicates that the compound is acyclic or open chain.

5. Secondary prefix : In IUPAC system of nomenclature, certain groups are not considered as
functional groups but are treated as substituents. These are called secondary prefixes and are added
immediately before the word root (or the primary prefix in case of carbocyclic compounds) in
alphabetical order to denote the side chains or substituent groups. The secondary prefixes for some
groups which are always treated as substituents groups (regardless of the fact whether the organic
compounds is monofunctional or polyfunctional) are given below :

S.
Organic Compounds Secondary prefix Word root Word root IUPAC name
No.
1 CH3CH2–Br Bromo eth ane Bromoethane
2 CH3–NO2 Nitro meth ane Nitromethane
3 C2H5–OC2H5 Ethoxy eth ane Ethoxyethane

In case of carbocylic compounds, primary prefixes are also used.

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IUPAC Nomenclature and Common Names
Br
4
CH
5 3
H2C CH2 4-Bromo + Cyclo + hex + an (e) + 1- ol
2 Secondary Primary Word Primary Secondary
H2C 6 CH2
prefix prefix root suffix suffix
CH
1

OH

IUPAC nomenclature of branched/complex alkanes :

(1) (a) Select the longest chain of carbon atoms in the molecule.
(b) Count the number of carbon atoms in that chain and name according to the following rules.
Example :
CH2–CH3
4 5 6 7
CH3–C–CH2–CH2–CH3
3 2 1
CH2–CH2–
CH3chain has 7 carbons.
Longest
hept ane
 It is a +
word root primary suffix
When chains of equal lengths are competing for selection, that chain is selected which has more
number of substituents.
CH3 CH3
Right CH3–H2C–CH–CH–CH3 Wrong CH3–CH2–CH–CH–CH3
CH–CH2–CH2–CH3 CH–CH2–CH2–CH3
CH2–CH2–CH3 CH2–CH2–CH3
7C in parent chain 7C in parent chain
with 3 side chains with 2 side chains
Here the chain shown is selected.

(2) Carbon atoms in the longest chain selected as above in numbered consecutively form one end to the
other such that the substituents attached get the lowest number.
In the above example, according to this rule, the numbering will be done as :
CH3 CH3
3 2 1
Right CH3–H2C–CH–CH–CH3 Wrong CH3–CH–CH–CH3
5 6 7
4 5 6 7
CH–CH2–CH2–CH3 4 CH–CH2–CH2–CH3
3 2 1

CH2–CH2–CH3 CH2–CH2–CH3

By this numbering, locant (substituents) get the number 2, 3 and 4 compared to 4, 5 and 6 if numbering
is done from other end.

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(3) Each substituent, which obviously, is an alkyl group is named according to number of carbon atoms
present in it and it is prefixed by the number to which it is located in the main chain. In the above
example, substituents are as following:
– CH3 (methyl) group at carbon NO. 2  2-methyl
– C2H5 (ethyl) group at carbon NO. 3  3-ethyl
– CH2CH2CH3 (propyl) group at carbon NO. 4  4-propyl
Hence, the above compound is named as : 3-Ethyl-2-methyl-4-propylheptane

(4) If the same substituent occurs more than once in the molecule, the prefix di (for two), tri (for three),
etc. used to indicate how many times it appears.
The above example can be written with a little modification as :
Example :
H3C CH3
3 2 1
CH3–H2C–C—CH–CH3
4 5 6 7
CH–CH2–CH2–CH3
CH2–CH2–CH3
Methyl at No. 2, 3, Ethyl at no. 3, propyl at no.4
This will be named as : 3-Ethyl-2,3-dimethyl-4-propylheptane

(5) The name of the compound is composed in such a manner that each substituent with its number and
name is written alphabetically just before the parent’s name. Prefixes di, tri, tetra etc. are not
considered in deciding alphabetical order.
 Ethyl will be written before methyl which will be written before propyl.
Note that in the above examples, this pattern has been compiled with.
*Also, as per convention,
(i) numbers are separated each other by commas.
(ii) numbers are separated from words by hyphens and
(iii) write the name of the compound as a single word (with no space between)

IUPAC nomenclature of alkenes :

Functional group : –C=C–
(1) Select the longest chain containing carbon-carbon double bond. This need not be the longest chain in
the compound as a whole. Parent name will be alkene corresponding to number of carbon atoms in the
longest chain.
CH3

CH3–CH2–C–CH=CH2

CH2

CH2
CH3
Longest chain is as shown above it has 6 atoms  hexene = parent name

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IUPAC Nomenclature and Common Names
(2) Carbon atoms in the longest chain is numbered so that doubly bonded carbon atom gets the lowest
number. The position of double bond is indicated by the smaller of the numbers assigned to two carbon
atoms of double bond.
 The above example can be rewritten as,
CH3
3 2 1
CH3–CH2–C–CH=CH2
4 CH2

5 CH2

6 CH3
Position of double bond will be indicated as no. 1.
Hence, name will be, 3-Ethyl–3–Methylhex–1–ene
CH3 CH3
6 5 4 3 2 1
Example : CH3–C–CH=CH–C–CH3

CH3 CH3
2,2,5,5–tetramethylhex–3–ene

Illustration 4:
Write the IUPAC name of the following compounds :
H3C CH2–CH3
CH3–CH2–CH–CH–CH–CH=C–CH3
CH2 CH3
CH2
CH–CH3
CH3
Solution:
5–Ethyl–2,6–dimethyl–4–(3–methylbutyl)oct–2–ene

Illustration 5:
Draw the bond line structures of the following compounds.
(a) 2–Methyl–3–heptene (b) 2, 6–Dimethyl hepta –1, 5–diene
Solution:

(a) (b)

IUPAC nomenclature of alkynes (– C  C – group) :

Numbering of longest chain is exactly same as that for naming alkenes.
Example
CH3–CC–CH3
But–2–yne

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Illustration 6:
Write the IUPAC name of the following compounds :

(a) CH3–CH–C C–CH3 (b)

CH3
Solution:
(a) 4–Methyl–2–Pentyne (b) 4–Propyl–2–heptyne

Illustration 7 :
Write the IUPAC name of the following compounds :
CH
3
H3C–CH2–C–CH–CCH
H3C CH3
Solution:
3, 4, 4–trimethyl–1–hexyne

IUPAC nomenclature of hydrocarbons containing both double and triple bonds

occurring only once :
(i) Such hydrocarbon is named as alkenyne (not alkynene).
(ii) Numbering is done in a manner that double and triple bonds get the lowest possible number.
In case of a choice, the double bond is given preference over triple bond.
Example : CH3–CH=CH–C CH
5 4 3 2 1  multiple bonds at (1) & (3)
Note 1 2 3 4 5  multiple bonds at (2) & (4)
 Name will be Pent –3–en–1–yne
HC  C – CH2– CH = CH2
5 4 3 2 1  Pent–1–en–4–yne
(Here there is a choice : if we number from other side)
HC  C – CH2– CH = CH2
1 2 3 4 5
again multiple bonds are at numbers (1) and (4)
So, here we will give preference to double bond over triple bond.

IUPAC nomenclature of alicyclic compounds :

(1) The names of alicyclic compounds are obtained by adding the prefix "cyclo"

Cyclobutane Cyclopentene

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IUPAC Nomenclature and Common Names
(2) The numbering of the carbon atoms in the ring is done in such a way that the substituent which comes
first in the alphabetical order is given the lowest possible number provided it does not violate the
lowest set of locants rule
Example :
CH3
4
CH3 C2H5
5 3 3
3
4 4 2
2 2
6
CH2CH3 5
CH3
5 1 1
1
6 CH2CH3 CH3 6 CH3
1–Ethyl–3–methyl 2–Ethyl–1,4–dimethyl 3–Ethyl–1,1–dimethyl
cyclohexane cyclohexane cyclohexane
(3) When the ring contains more or equal number of carbon atoms than the alkyl group attached to it, then
it is named as a derivative of cycloalkane and the alkyl group is treated as substituent
Example :
CH2–CH2–CH3

Propylcyclopropane Cyclohexylcyclohexane
(4) The alkane chain contains greater number of carbon atoms than present in the ring, the compound is
considered as the derivative of alkane and the ring is designated as substituent.
Example :
1 3 CH3–CH2–CH––CH2–CH2–CH3
2
4

2-Cyclopropylbutane 3–Cyclopentylhexane
(5) If ring has unsaturation and side chain is saturated then ring is selected as parent chain.
If side chain has unsaturation and ring is saturated then side chain is selected as parent chain.
If both have unsaturation the chain with maximum unsaturation has selected as parent chain.
If equal unsaturation then longest chain is selected as parent chain.
If unsaturation and number of carbon atoms both are equal then ring is selected as parent chain.
Example :
6 3
1 2
5 4

2 5 1
4
6
3

1–Ethyl Cyclohex–1–ene 6–Ethyl–3,3–dimethyl cyclohex–1–ene

3 2 1 1 2 3 4 5 6
CH2–CH=CH 6
CH2–CH2–CH=CH–CH2–CH3
5
1

4 2

3–Cyclopropyl prop-1-ene 1-(Hex-3-ene) Cyclohex-1-ene

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 JEE (Main + Advanced) : Chemistry
(6) If, more than one alicyclic ring is attached to a single chain, the compound is named as a derivative of
alkane and the ring is treated as a substituent group.
Example

CH2

Dicyclopropylmethan 1,3-Dicyclohexyl propane 1-Cyclohexyl-4-cyclopropylbutane

e
(7) If a multiple bond and some other substituents are present in the ring, the numbering is done in such
a way that the multiple bond gets the lowest number.
Example :
NO2
3
4 2

5 1
6
3-Nitrocyclohex-1-ene
(8) If a compound contains an alicyclic ring directly linked to the benzene ring. It is named as a derivative
of benzene.
Example :
5 6 2 3

1 1 4
4 NO2
3 2 6 5

CH3
Cyclo hexyl benzene 1–(2–Methylcyclohexyl)–4–nitrobenzene
(9) If functional group is present in cyclic compounds then main chain is taken where principal functional
group lie, if the principal functional group is present in ring also then main chain will be taken for the
maximum no. of carbon atoms.
OH
1 1 3
2
6 2
5 3
OH
4
2–propylcyclohexan–1–ol 1–Cyclohexyl propan–2–ol
(10) When chain terminating functional group is directly attached with ring then ring is taken as parent
chain & special suffix used for functional group.
S. No. Functional Group Suffix
1 —CHO Carbaldehyde
2 —COOH Carboxylic acid
3 —COX Carbonyl halide
4 —COOR Alkyl Carboxylate
5 —CONH2 Carboxamide
6 —CN Carbonitrile

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IUPAC Nomenclature and Common Names
Example :
CN CHO

Cyclohexane Carbonitrile Cyclohexane Carbaldehyde

IUPAC nomenclature of compounds containing functional groups :

Functional Groups

Non chain terminating Chain terminating

O
(i) –N=N– (i) –C–OH

(ii) –C– (ii) –C–OR

O O

(iii) –X (iii) –C–X

O
(iv) –C–O–C– (iv) –C–NH2
O O O
(v) –O– (v) –CN
(vi) –CHO

Rules for non chain terminating functional groups :

(A) Parent chain : Select the longest possible chain with maximum functional group and maximum
unsaturation.
(B) Lowest number for the functional group :
Numbering is done from that side of the chain which gives lowest locant to the principle functional
group followed by double and triple bonds.
Example :
O O
1 2 3 4 5 6
6 5 4 3 2 1
CH3–CH–CH2–C–CH2–CH3 CH3–CH–CH2–C–CH2–CH3

CH3 CH3
(I) correct (I) wrong

( C=O group gets lowest number 3) ( C=O group gets number 4 which is not lowest)

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 JEE (Main + Advanced) : Chemistry
Rules for chain terminating functional groups :
(1) When a chain terminating functional group such as –CHO, –COOH, – COOR, –CONH2, –COCl, – CN etc.
is present, it is always given number 1 (one.)
Example :
O
4 3 2 1
CH3–CH2–CH–C–OH O
5 41 3 2
CH3 CH3–CC–CH2–C–H
2–Methylbutan–1–oic acid Pent-3-yn-1-al

(2) If a compound contains two or more like groups, the numerical prefixes di, tri, tetra etc. are used
Example :
CH2 CH CH2 CH3–C–CH2–C–CH3
OH OH OH O O
Propane –1,2,3–triol Pentane–2, 4–dione
(3) The name for benzene as substituent is phenyl. In case the phenyl ring is further substituted, the carbon
atoms of the ring directly attached to the parent chain in such a ways that the substituent on the ring
gets the least possible number.
Example :
H3C O
2 1 CH3–C – C–OC2H5
CH–CCl3 1
2 1

3 NO2
1,1,1-Trichloro-2,2-diphenyl ethane Ethyl–2–methyl–2–(3–nitrophenyl) propanoate

(4) If the organic molecule contain more than one similar complexes subtitutents, then the numerical
prefixes such as di, tri, tetra etc. are replaced by bis, tris, tetrakis etc. respectively.
Example :
HO–CH2–CH2–O
CH2–COOH 2 8
10
HO–CH2–CH2–O 1
4 6
3 5 7 9

2,2–Bis–(2–hydroxyethoxy) ethanoic acid 4,6-Bis-(1,1-dimethylethyl) decane

Rules for IUPAC nomenclature of polyfunctional compounds :

1. When an organic compound contains two or more different functional groups then one functional
group is selected as the principal functional group while other groups are treated as substituents.

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IUPAC Nomenclature and Common Names
S. NO. Functional group Prefix Suffix
1. z— (C)OOH (carboxylic × oic acid
— COOHacid) carboxy carboxylic acid
2. — SO3H (sulphonic acid) sulpho sulphonic acid
O
(C)
3. O (anhydride) × oic anhydride
(C)
O

4. — (C)OOR (ester) × alkyl ------ oate

— COOR alkoxy carbonyl alkyl-----carboxylate
or carbalkoxy carboxylate
5. — (C)OX (acid halide) × oyl halide
— COX halo formyl carbonyl halide
6. — (C)ONH2 (amide) × amide
— CONH2 carbamoyl carboxamide
7. — (C)N (cyanide) × Nitrile
— CN cyano carbonitrile
8. —N C (isocyanide) × isonitrile
— NC isocyano/carbyl amino ×
9. —CHO formyl carbaldehyde
(C) (Ketone)
10. keto/oxo one
O
11. — OH (alcohol) hydroxy ol
12. — SH (thio alcohol) mercapto thiol
13. — NH2 (amine) amino amine
14. — OR (ether) alkoxy ×

2. Some functional group such as all halo groups. (Fluoro, bromo, chloro, iodo) nitrosol, (NO) nitro (–NO2) are
always treated as substituent.
Example :
NH2
5 4 3 2 1
CH3–CH–CH–CH–CH3
Cl OH
4–Amino–3–chloropentan–2–ol
(–NH2 & –Cl group treat as substituent)
Numbering the principal chain order is
[Principal functional group > double bond > triple bond > substituents]

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 JEE (Main + Advanced) : Chemistry
Example :
O
6 4
CH3 –C–CH–COOH O 5
O=CH– CH–CH–C–CH–COOH
3 2 1
5 4 3 2 1
O CH3 –C–CH2–CH2–CHO 3,6–Dioxohexanoic acid
3–Oxobutan–1–oic acid 4–Oxopentan–1–al or 5-formyl–3–oxopentanoic
[–COOH > – CO] [–CHO > C=O] acid [COOH >–C– & CHO]
O
3. The longest possible chain of carbon atoms containing the principle functional group and maximum
number of multiple bonds is selected as parent chain.
Example :
4 3 2
(a) CH3 –CH2–CH–CH2–CH3
1
CH2OH
parent chain contains four rather than five carbon atoms.
O
(b) CH3–CH2–CH2–CH–CH2–C–O–C2H5
3 2 1
CH=CH2
4 5

parent chain contains five rather than six carbon atoms.

O
(c) CH3–CH–CH2–C–O–C2H5
3 2 1
CH=CH2
4 5
Ethyl–3–methyl–4–pentenoate
O
CH3 C–NH2
4 1
3 2
(d) CH3 –CH–CH–CHCH3
CH3 CH3
3,3–Dimethyl–2–(1–methylethyl) butanamide
4. If more than one same chain terminating group are present then the principal chain is selected
including the functional groups and numbering is done from that side which gives lowest locant to
unsaturation substituent.
Example :
1 2 3 4 5
NC–CH–CH2–CH2–CN
HOOC–CH2–CH2–COOH
1 2 3 4 CH3
Butane–1,4–dioic acid 2-Methylpentanedinitrile

Illustration 8 :
Write the IUPAC name of
3 4 5
CH3–CH2–CH–CH2–CH–CH3
1 2 6 7
CN–CH2 CH2–CH3

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IUPAC Nomenclature and Common Names
1. The longest chain containing functional group is of 7 carbon atoms. Therefore, the word root is hept &
the chain is numbered as shown.
2. There is no multiple bond in it. Hence, the primary suffix is ane.
3. The functional groups is –CN. Hence , secondary suffix is nitrile.
4. Moreover, there is a methyl groups on carbon 5 and ethyl group on carbon 3.
5. The IUPAC name is, therefore, 3–Ethyl–5–methylheptanenitrile

Illustration 9:
Write the IUPAC name of
7 6 5 4 3 2 1
CH3–CH2–CH–CH=CH–CH2–CHO
CH3
1. The longest chain containing functional group is of seven carbon atoms. Therefore, word root is hept.
2. As C=C double bond is present in the molecule. Thus, primary suffix is ene.
3. The secondary suffix is al because of presence of –CHO group.
4. The chain is numbered as shown so that carbon atoms of –CHO group gets number 1.
The methyl group is present on carbon 5 while position of double bond is 3. Thus, IUPAC name is
5–Methylhept–3–en–1–al

Bicyclic :
Bicyclo : When two rings are fused at two carbon then prefix Bicyclo is used.(Carbon chain should be taken
in decreasing order)
(i) Two fused or bridged rings are called bicycloalkanes.
(ii) Total number of carbon atoms present in both the rings is considered as parent alkane.
(iii) Common carbon atoms present in both the rings are referred as principal points of the bridge.
(iv) The line joining the principal points is called the bridge line. Bridge line can have 0. 1. 2 etc carbon atoms.
(v) The name is written as bicyclo [x. y. z] alkane. x. y. z are in the decreasing order.
(vi) The numbers are separated by full stops.

Bicyclo [4.4.0] decane Bicyclo [4.3.0] nonane Bicyclo [2.2.0] hexane

Bicyclo [1.1.0] butane Bicyclo [2.2.1] heptane Bicyclo [2.2.2] octane

Spiro : When two rings are fused at one carbon the prefix spiro is used (Carbon chain should be taken in
increasing order)

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 JEE (Main + Advanced) : Chemistry
1. A molecule that has two rings sharing a single atom is called spirocyclic.
2. The numbers of skeletal atoms linked to the spiro atom are indicated by arabic numbers, separated by
a full stop.
3. The numbers are written in ascending order and enclosed in square brackets.
4. Numbering of a spiro bicyclic hydrocarbon starts with a ring carbon next to the spiro atom and
proceeds first through the smaller ring and then through the spiro atom and around the second ring.

Example :
6
8 9 1 6 7
7 5 1
4
7 2
4 1 5 3
8 3 2
6 5 4
3 2
Spiro[3.5] nonane Spiro[2.4] heptane
Spiro[3.4] Octan
octane

Spiro [4.4] nonane

Spiro [2.4] heptane Spiro [2.2] pentane
7
6 1

3
5 2
4O

4–oxa spiro [2.4] heptane

Nomenclature of aromatic compounds :

The aromatic compounds are cyclic compounds contains one or more benzene type rings. Benzene is the
simplest hydrocarbon of aromatic series which has planar cyclic ring of six carbon atoms having three
double bonds in alternate positions as shown below.
CH 1
HC CH 6 2
or
HC CH 5 3

CH 4

(A) Nuclear substituted –

The functional group is directly attached to benzene ring in the IUPAC system, they are named as
derivative of benzene. The position of the substituents in disubstituted benzenes are indicates either
by prefixes such as o–(ortho) for 1, 2, m–(meta) for 1, 3 and p (para) for 1, 4 position. However, many
of their common names have also been adopted by the IUPAC system.

(B) Side–Chain substituted –

The functional group is present in the side chain of the benzene ring in the IUPAC systems, these are
usually named as phenyl derivatives of the corresponding aliphatic compounds.
The IUPAC and common names of a few important members of each formly are given below :
(a) Aromatic hydrocarbons (arenes) : Hydrocarbons which contain both aliphatic and aromatic units
are called arenes. These are of two types
(i) Hydrocarbon containing one ring only.

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IUPAC Nomenclature and Common Names
Example :
CH3
1 1 2 3
CH3 CH3 CH3–CH–CH3
1 1 2
CH3
2 2 3

4
CH3
3
CH3
1,2–Dimethyl benzene 1,3–Dimethyl benzene 1,4–Dimethyl benzene Isopropyl benzene
(o–Xylene) (m–Xylene) (p–Xylene) (Cumene)

CH=CH 3 2 1
C CH
3 2 1
CH2–CH=CH2 CH2–CH CH

Ethenynl benzene 3-propenyl benzene Ethynyl benzene 3-propynyl benzene

(Styrene) (Allyl benzene) (Phenyl acetylene) (Propargyl benzene)
Aryl groups :
CH2⊝ CH
CH

Phenyl
bbnbBenzyl Benzal Benzo
CH3 CH3 CH3
1 1 1

2 2 2
3
3 4
2-Tolyl 3-Tolyl 4-Tolyl
or o-Tolyl or m-Tolyl
or p-Tolyl
Halogen derivatives :
CH3 Cl
1
Cl 1
Cl
1 2
2
3
4

1,2-Dichlorobenzene Cl
Chloro benzene 1,4-Dichlorobenzene
or o-Dichlorobenzene or p-Dichlorobenzene
Hydroxy derivatives :
The nuclear hydroxy derivatives are called phenols while the side chain substituted hydroxy derivatives
are called aromatic alcohols.
(i) Phenols–monohydric
OH
OH 1
2
3
4

Hydroxybenzen CH3
4-methyl phenol
e (phenol)
(p-cresol)

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 JEE (Main + Advanced) : Chemistry
(ii) Dihydric and polyhydric phenols
OH
OH OH
1
1
OH 2
2

3
OH
Benzene-1,2-diol Benzene-1,3-diol OH
(Catechol) Benzene-1,4-diol
(Resorcinol)
(Quinol)
(iii) Aromatic Alcohols :
2 1
CH2OH CH3CH–OH
 

1-phenyl ethanol
Phenyl methanol
(Benzyl alcohol) (-phenyl ethyl alcohol)

(iv) Aromatic ethers

OCH3 O–C6H5

Methoxy benzene Phenoxy benzene

(Anisol) (Diphenyl ether)
(v) Aldehydes
CHO  
CHO 1
OH CH2CH2–CHO
2

2-Hydroxy benzaldehyde 3-phenylpropanal

Benzaldehyd (Salicylaldehyde) -phenylpropionaldehyde
e
(vi) Ketones
1 2
COCH3 COC6H5

1-phenyl ethanone Dephenylmethanon

(Acetophenone) e(Benzophenone)

(vii) Nitro Compounds

NO2
1
NO2
2

3 NO2
1,3-Dinitrobenzene
Nitrobenzene (m-Dinitrobenzene)

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IUPAC Nomenclature and Common Names
(viii) Amines
(a) Aryl amines
NH2 NH2
NH2

Benzenamin Benzene-1,2-diamine
e (Aniline) (o-phenylenediamine)
(b) Aryl alkyl amine
 
CH2NH2 CH2–CH2–NH2

Phenyl methanamine 2-phenyl ethanamine

(Benzylamine)
(-phenyl ethyl amine)
(ix) Arenediazonium Salts :

   ⊝
N N.Cl N NHSO4

Benzene diazonium chloride Benzene diazonium hydrogen sulphate

(x) Cyanides and Isocyanides

C N N C

Benzonitrile Phenyl isocyanide or

or Phenyl Cyanide Phenyl carbylamine
(xi) Carboxylic Acids
COOH COOH
1
COOH 1
CH3 COOH
2 2

2-Methyl benzoic acid Benzene-1,2-dicarboxylic

Benzoic acid
(o-toluic acid) acid (Pthalic acid)
(xii) Anhydrides
O O
C6H5–C–O–C–C6H5
Benzoic anhydride
(xiii) Esters (xiv) Amides
O
3
CH3 4
2 C–NH2
1
O
O–C–CH3
4-Methyl phenyl ethanoate Benzamid
e
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 JEE (Main + Advanced) : Chemistry
Essential common names :

ALKANE Aceto Acetic Ester

CH3–CH–CH–CH3 CH3–C–CH2–C–O–C2H5 (AAE) or
1. Isopentane 16.
CH3 O O Ethyl Aceto
Acetate
ALKENE
2. CH2=C=CH2 Allene N–DERIVATIVES

ALKYL HALIDE Vinyl Cyanide

17. CH2=CH–CN
3. or Acrylo Nitrile
CHCl2 Westron NH2–C–NH2
. 18. Guanidine
CH3 (Solvent)
O
Westrosol or AROMATIC COMPOUNDS
4. ClCH=CCl2 Triclean
Anthracene
(Solvent) 19.
ALCOHOL
5. CH–OH Glycol or 20. Thiophene
CH2–OH Ethylene Glycol S

CH2–CH–CH2 SO3H
21. NH2 Sulphanilic acid
6. Glycerol
OH OH OH
7. CH2=CH–CH2–OH Allyl Alcohol
22. Azulene
8. CH2=CH–OH Vinyl Alcohol
ETHER
Anisole 23. Napthalene
9. C6H5–O–CH3 (Methyl Phenyl
Ether) CH3
KETONE CH3
24. o–xylene
10. CH3COCH3 Acetone
CARBOXYLIC ACID
HO–CH–COOH 25. CH3
Malic acid
11.
CH2–COOH
m-xylene
12. HO CH2 COOH Glycolic Acid
COOH CH3
13.
CH2 Malonic acid
COOH 26. NO2
14. CH2–COOH Nitrobenzene
Succinic acid
(oil of mirbane)
CH2–COOH

15. CH2–COOH
CH2 Glutaric acid
CH2–COOH

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IUPAC Nomenclature and Common Names
NH2 COO
27. H
SO3H
Orthanilic Acid 34. Terephthalic acid

COO
H CO2H Anthranilic acid
CH3
28. OH 35. (o-aminobenzoic
o-Cresol NH2 acid)
36. C6H5CHO Benzaldehyde
CH3 HETROCYCLIC COMPOUNDS

29. m-Cresol
37. N Pyrrolidine
OH
H
30. C6H5CO3H Perbenzoic acid

COOH 38. N Piperidine

CH3
H

Tetrahydrofuran
39.
o-toluic acid, O (THF)
m.p. 105°C
Oxirane or
COOH CH2–CH2
Ethylene Oxide
40.
O or Oxo Cyclo
Propane
31. CH3 Toluic acids
m-toluic acid, 41. Quinuclidine
m.p. 111°C N
COOH NH2
42. Aniline

SOME REAGENTS
CH3 43. Grignard’s reagent RMgX
p-toluic acid, NBS
m.p. 180°C O
N-Bromosuccini
COOH 44.
NBr mide
32. Phthalic acid
COOH O
COOH POLAR PROTIC SOLVENTS
45. H –O–H Water
33. Isophthalic acid
46. R–O–H Alcohol
COOH

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 JEE (Main + Advanced) : Chemistry
OH Hexamethylphos
52.
47. Phenol HMPT or HMPTA phoramide
O=P–(NMe2)3
Dimethyl
CH3–C–OH
48. Acetic acid formamide
O 53. DMF
H–C–NMe2
Hydrogen O
49. HF
Fluoride
Polar Aprotic Solvents Crown ethers
Dimethyl O
50. DMS sulphide 54. O O Cyclic polyethers
CH3–S–CH3 O
Dimethylsulphoxi
51. DMSO (12 – C – 4)
de Me2S=O

55. NH3 Ammonia

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