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com

1 The purpose of the IUPAC system of nomenclature

is to establish an international standard of naming
compounds to facilitate communication. The goal

m
of the system is to give each structure a unique
and unambiguous name, and to correlate each

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name with a unique and unambiguous structure.

Nomenclature
In this Chapter, we will develop the knowledge of
using IUPAC conventions for naming an organic

ing
compound and to write the appropriate structure of
a compound from its given IUPAC name.

of Organic
ch

Compounds
oa
yC

Learning Framework
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of the Chapter . . .
k
pic

1-1  Introduction
1-2  Naming Hydrocarbons According to IUPAC
w.

Conventions
1-3  Naming Compounds Containing One or More
ww

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.

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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.

m
1-1A  The IUPAC Systematic Approach to Nomenclature

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A rational nomenclature system should do at least two things. First, it should indicate how the carbon atoms of a given
compound are bonded together in a characteristic lattice of chains and rings. Second, it should identify and locate any
functional groups present in the compound. Since, hydrogen is such a common component of organic compounds, its

ing
amount and locations can be assumed from the tetravalency of carbon, and need not be specified in most cases. The IUPAC
nomenclature system is a set of logical rules devised and used by organic chemists to circumvent problems caused by arbitrary
nomenclature. Knowing these rules and given a structural formula, one should be able to write a unique name for every
ch
distinct compound. Likewise, given a IUPAC name, one should be able to write a structural formula. In general, an IUPAC
name will have three essential features
•• A root or base indicating a major chain or ring of carbon atoms found in the molecular structure.
oa

•• A suffix or other element(s) designating functional groups that may be present in the compound.
•• Names of substituent groups, other than hydrogen, that complete the molecular structure.
yC

As an introduction to the IUPAC nomenclature system, we shall first consider compounds that have no specific functional
groups. Such compounds are composed only of carbon and hydrogen atoms bonded together by sigma bonds (all carbons are
sp3 hybridized).
M

According to IUPAC conventions, organic compounds are classified into two broad categories for the purpose of naming-
One being “hydrocarbons” – which contain only carbon and hydrogen and other being “derivatives of hydrocarbon” which,
k

besides containing carbon and hydrogen, also contain some other atoms viz. oxygen, nitrogen, halogen, sulphur etc.
pic

1-2  Naming Hydrocarbons According to IUPAC Conventions

w.

1-2A  Saturated Unbranched-Chain Hydrocarbons

The first four saturated unbranched acyclic (non-cyclic) hydrocarbons are called methane, ethane, propane and butane.
ww

Names of higher members of this series consist of a numerical term followed by “ane”. Examples of few unbranched,
saturated, acyclic hydrocarbons are shown in the Table 1.1.
Table 1.1  (n = Total number of carbon atoms)
n Name n Name n Name n Name
5 Pentane 14 Tetradecane 23 Tricosane 50 Pentacontane
6 Hexane 15 Pentadecane 24 Tetracosane 60 Hexacontane
7 Heptane 16 Hexadecane 25 Pentacosane 70 Heptacontane
8 Octane 17 Heptadecane 26 Hexacosane 80 Octacontane
9 Nonane 18 Octadecane 27 Heptacosane 90 Nonacontane
10 Decane 19 Nonadecane 28 Octacosane 100 Hectane
11 Undecane 20 Icosane 29 Nonacosane
12 Dodecane 21 Henicosane 30 Triacontane
13 Tridecane 22 Docosane 40 Tetracontane

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Nomenclature of Organic Compounds    Chapter 1    3

1-2B  Structural Formula and Bond-Line Structure

Structural formula of a compound demonstrate the connectivity of atoms in the molecule ie, it represents a specific
bonding pattern, a characteristic of the given molecule. Some of the structural formula and its descriptions are mentioned
below :
H H H
H H H H H H H H H
H C C C
CH3CH2CH2CH2CH2CH3 H—C—C—C—C—C—C—H C C C H
n-hexane H H
   H H H H H H    H
H H H

H H HH
H H HH
C HH H
CH3 H H H H C H H H H C H

m
H—C—C—C—C—C—C—C—H H C C C H
H3C—CH—CH2CH2—C—CH2CH3 C C C C
H

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CH3 CH3 H C H H C H H H H
H H C H
2, 5, 5-trimethyl heptane H H
  HH HH   H HH

ing
As shown in the above structures, carbon is tetravalent and associated with four covalent bonds (C—H or C—C bonds).
ch
1-2Aa  Bond-Line Structures (Topological Structures)
In frequent writing, organic molecules are usually represented by a line structure in which letters ‘C’ for carbon and ‘H’
oa

for hydrogen are not shown. In topological structure, each point of inflexion and the terminal points represent carbon atoms
and the visible line between two points represents carbon-carbon bonds. At each carbon, the number of hydrogen equals to
(4–the no. of visible bonds at that carbon) eg,
yC

H H H H H H
M

H—C—C—C—C—C—C—H =
H H H H H H
k

n-hexane
pic

H
H H
H H H H C H H
w.

H—C—C—C—C—C—C—C—H=
3C—C bonds
ww

H C H H C H H ie, one H 4C—C bonds

ie, no H
H HH H HH
2, 5, 5-trimethyl heptane

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

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4   Essential Organic Chemistry

1-2Ab  Univalent Radicals

Univalent radicals derived from saturated unbranched hydrocarbons by removal of one hydrogen atom from a terminal carbon
atom are named by replacing –“ane” of the parent name by “yl”. The carbon atom with the free valence is numbered as 1.
4 3 2 1
CH3CH2CH2CH2—Butyl
10 1
H3C—(CH2)8—CH2—Decyl etc.

1-2C  Saturated Branched-Chain Acyclic Hydrocarbon

In case of a saturated, branched chain hydrocarbon, following rules are applicable in the same sequence
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

m
H 3C CH3
(1) CH3

.co
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.

ing
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
ch
CH3
H 3C
CH3
oa

CH3 CH 3
(2)
yC

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-
M

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
k

before the locants. Adjacent numbers must be separated by comma (,).

pic

Applying the above mentioned rules, compounds (1) and (2) described just before can be named as
CH3
6 4 2 6 4
w.

7 5 3 1 H 3C 5 3 2
1
H 3C CH3 CH3
CH3 CH3 CH3
ww

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)

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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

m
Isobutane Isopentane Neopentane Isohexane

.co
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

ing
12 10 8 6 4 2
13 11 7 5 1
H3C 9 3 CH3
5
H3C 2 Here the branch is dimethylpentyl as
ch
3 1 CH3 CH3
4 complete single substituent
CH3
oa

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
yC

at the lowest number as

4
H3C 3 2
4
H3C 3 CH3 CH3
M

2 1
H3C 1 8 7
4
3 CH3
1 5
H3C
k

6 2
12 10 6 4 2
13
pic

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
w.

will have priority since, it has locant at C-1 while other has locant at C-2
ww

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

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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

Correctly numbered (four locants) (Three locants) (Two locants)

2, 3, 5-trimethyl-4 propylheptane (Wrongly numbered)

(b) The chain whose side chain has lowest numbered locants
CH3 CH3
7

m
6
H3C H3C 5
CH3 CH3

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6
7 5 3 3
4 2 4 2
H3C CH3 H3C CH3
1 1
CH3 CH3

ing
Correctly numbered (locants are at Wrongly numbered : locants
2,4,5 positions) 4-isopropyl-2,5- are at 2,4,6 positions
dimethylheptane
ch
(c) The chain having the greatest number of carbon atoms in the smaller side chain
oa

H3C
yC

H3C

H3C
M

12 10 6 2
13 11 9 5 3 1
8 7
k

4
H3 C CH3
pic

CH3 CH3 CH3

CH3
H3C
w.

CH3 CH3
7,7-Bis(2,4-dimethylhexyl)-3-ethyl-5,9,11-trimethyltridecane
ww

(d) The chain having the least branched side chain

CH3 CH3
1 2 4
3 5
H3C CH3 H3C CH3
12 12
10 2 10
H3C 9 7 5 3 1 H3 C 11 9 7
8 6 4 CH3 8 6 CH3
11
CH3 CH3

6-(1-isopropylpentyl)-5-propyldodecane Wrongly numbered

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Nomenclature of Organic Compounds    Chapter 1    7

Problem 1-1 Write IUPAC names of the following hydrocarbons

I II III

IV V
6 4 2 2 4 6
 7 5 3 1 5
1 3 7

I II

m
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

.co
obtained from both terminals, preference difference determine the numbering
goes to alphabetical order. pattern-here 3,3,5 not 3,5,5.
3

ing
4 1
2 8 2
9 7 5
1 4 6
3 5 7 10
8 6
ch
III IV
6-ethyl-3,4-dimethyl octane 5-butyl-5-methyl-4-propyl decane
oa

Longest chain with maximum number of locants

becomes the parent chain.
4
yC

3 5
2
1 6 7
M

V
3,5-diethyl-2,3,5,6-tetramethyl heptane
k

Longest chain with maximum number of locants becomes the parent chain.
pic

Problem 1-2 Write. structural formula of the following hydrocarbons

(I ) 4-ethyl-2,2,6,6-tetramethyl heptane.
w.

(II ) 4-ethyl-2,3-dimethyl hexane.

(III ) 6-ethyl-3-methyl-5-propyl nonane.
(IV ) 5-(1,2-dimethylpropyl )-5-(2,2-dimethylpropyl ) nonane.
ww

(V ) 5-(1,2-dimethylpropyl )-6-(1-ethylpropyl ) decane.


I II III

IV V

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8   Essential Organic Chemistry

Problem 1-3 Write IUPAC names of the following hydrocarbons

I II

III IV

m
3
2

.co
1
8 4 2
3 1
 9 7 6 2 4 8 10
5 5 6 7
2 3 1 3 9

ing
1

I II
ch
5-(1-ethyl-2, 2-dimethylpropyl)-5 5-(1, 1-dimethylpropyl)-6-
-(1, 2, 2-trimethylpropyl) nonane (2, 2-dimethylpropyl) decane
oa

2
10
3 1 9 7
6 11 8
7 4
yC

4 3
5 6
8 10 5
2
9
1
M

III IV
8-ethyl-2, 3, 8-trimethyl-4, 7-dipropyl decane 6, 7, 8-triethyl-3-methyl undecane
k
pic

Problem 1-4 Draw structures of all alkanes and write their IUPAC name having molecular formula C7H16.


w.

Heptane 2-methylhexane 3-methylhexane 2,2-dimethylpentane

ww

2,3-dimethylpentane 2,4- dimethylpentane 3-ethylpentane 2,2,3,-trimethyl butane

1-2D  Unsaturated Hydrocarbons

Rule 1  Unsaturated, unbranched acyclic hydrocarbons having one double bond are named by replacing “–ane” of the
name of corresponding saturated hydrocarbon with the ending “-ene”. If there are two or more double bonds, the ending will
be “-adiene”, “-atrine” etc. The chain is so numbered as to give lowest possible number to the double bond.
1
2 4 6 2 4 6
8
7 5 3 CH2
H3 C 3 5 CH3 H3C 3 5
CH3 H3C 6 4 2
1 7 1 7
3-heptene 2,4-heptadiene 1,3,5-octatriene

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Nomenclature of Organic Compounds    Chapter 1    9

Following unsystematic names are retained in IUPAC

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.
6 1
2 4 2 4 CH3 7 5 3
8 CH3
HC 3 CH3 H3C 3 5 H3C 6 4 2
1 5 1

Pentyne 2-hexyne 2,4,6-octatriyne

(Its triple bond is at terminal positions,
therefore, it need not numbered)

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”

m
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”.

.co
6
2 4 2 4
CH
H2C 3 5 HC 3 CH3
1 1 5

ing
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.
ch
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).
oa

1
4 2 7 5 3 CH3
5 1 8 4
HC CH2 H3 C
yC

3 6 2
CH3
1-penten-4-yne 4-methyl-6-octen-2-yne
M

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
k

done in alphabetical order. goes to lower number to other locant.

pic

Rule 5  Unsaturated branched acyclic hydrocarbons are named as derivatives of unbranched hydrocarbons which contain
maximum number of double and triple bonds.
w.

2 2
1 1
CH3 3 CH3 3 CH3
5 3 6
ww

6 CH2 4 CH2 4 CH2

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

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10   Essential Organic Chemistry

(i) That one with greatest number of carbon atoms

1
CH2 CH2
2
1 7
7 3 CH2 5 CH2
8
H3C 5 H3C 3
6 4 2 4 6
5-vinyl-1,3,5-octatriene The above numbering system also has
a main chain with three double bonds but one
carbon less than other chain (mentioned
on left)

(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

m
3 3
H2C CH2 not H2C CH2
5 5
6 4 2 4 2

.co
5-ethynyl-1,3,6-heptatriene
1 1
3 CH2 5 3 CH2

ing
4 2
not 6 4 2
5
6 CH2 CH2
ch
4-ethynyl-1,5-hexadiene 4-vinyl-1-hexen-5-yne
oa

Following name is retained for unsubstituted compound only

CH3
yC

CH2 CH2
H2C
H2C but
CH3 CH3
M

Isoprene 2,3-dimethyl-1,3-butadiene
not 3-methylisoprene
k
pic

Problem 1-5 Write IUPAC names of the following hydrocarbons

w.
ww

I II III

IV V
7 5
6 4
2 3 1
5 6 2 1
 1 4 5
4
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
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10
3 6 1
3
 6 4
2
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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

Problem 1-6 Write IUPAC names of the following hydrocarbons

m
I II III

.co
ing
IV V
1
2
ch
4 2 4 2 3 5
 5 3 1 5 3
1 4 6
oa

7 6
I II III
yC

4.4-dimethyl-1-pentyne 5-ethyl-5,6-dimethyl-2-heptyne 3-(1,2-dimethylpropyl)-1,5-hexadiyne

2 1
4
3 2
M

1 5
3
4
k

5
pic

IV V
3-(1-ethylpropyl)-1,4-pentadiyne 3-butyl-3-propyl-1,4-pentadiyne
w.

Problem 1-7 Write IUPAC names of the following hydrocarbons

ww

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.

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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')

Problem 1-8 Write structural formulas of the following hydrocarbons

(I ) 3-ethyl-5-methyl-1,6-heptadiene. (II ) 3,4-diethyl-1,4-hexadiene.
(III ) 5-hepten-1-yne (IV ) 4-ethenyl-3-ethyl-1,6-octadiene.
(V ) 3,3-diethynyl-1,4-pentadiyne.


I II III

m
.co
ing
IV V

Problem 1-9 Draw structures and write IUPAC name of all the alkenes with their molecular formula C5H10.
ch
oa


1-pentene 2-pentene 2-methyl-1-butene 3-methyl-1-butene 2-methyl-2-butene
yC

Problem 1-10 Draw structures and write IUPAC name of all the alkynes with their molecular formula C5H8.
M


k

1-pentyne 2-pentyne 3-methyl-1-butyne

pic

1-2E  Naming Monocyclic Hydrocarbons

Rule 1  Name of monocyclic, saturated hydrocarbons are formed by attaching the prefix “cyclo” to the names of acyclic,
w.

saturated hydrocarbon with same number of carbons

ww

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,
CH3
1
2 3 2
5
3 1
4
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
4
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H3C 3
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institute and H3C 3 12
1,2,4-trimethylcyclohexene 4-ethyl-5-methylcyclohexene 5-ethyl-4-methylcyclohexene
 CH3
1
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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

m
not 2,4,6-trimethylcyclohexene

.co
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

ing
6
CH3 5
1
2 3 4 CH2
1 5 3
2 4
ch
H3C
1-cyclopropyl-3-ethyl-2,4-dimethylhexane 1-cyclopentyl-3-ethyl-1,4-pentadiene
oa

Problem 1-11 Write IUPAC names of the following substituted cyclic hydrocarbons
yC
k M
pic

I II III IV V

Here numbering is done in alphabetical order because

w.

all locants are equidistant from one another

5 3

ww

1 3 5 1

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

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14   Essential Organic Chemistry

Problem 1-12 Write IUPAC names of the following substituted cyclic hydrocarbons

I II III

IV V

m
1 3
5 1 4


.co
4 5
2 7
3 6

I II

ing
5-ethyl-1,2-dimethyl-1,3-cyclohexadiene 3,7-diethyl-1,4-cycloctadiene

2
ch
1 1
4
3 2
oa

III IV
1,4-dicyclohexylcyclohexene 1,2,3-tricyclopropylcyclopropane
yC

2
4
1
M

V
4-cyclohexylcyclopentene
k
pic

Problem 1-13 Write IUPAC names of the following hydrocarbons

w.
ww

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

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Nomenclature of Organic Compounds    Chapter 1    15

Problem 1-14 Draw structures of the following hydrocarbons

(I ) 3,3-dimethylcyclohexene (II ) 4-ethyl-6-methylcycloheptene
(III ) 4,5-diethyl-7-methyl cycloctene (IV ) 1,4-dicyclopentylcyclopentene


I II III IV

1-2F  Substituted Aromatic Hydrocarbons

Following names for the substituted monocyclic aromatic hydrocarbons are retained
H3C CH3 CH3 CH2

m
.co
Benzene Cumene Toluene Styrene
CH3 CH3 CH3 CH3 CH3

ing
CH3

CH3 H3C CH3

ch
o-xylene m-xylene Mesitylene
CH3
p-xylene H3C CH3
Cymene
oa

Rule 1  Other monocyclic substituted hydrocarbons are named as derivatives of benzene or one of the compounds listed
yC

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
M

CH3
k

CH2
CH2 CH3
pic

1,4-divinylbenzene 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
w.

of 1,2- , 1,3- , and 1,4-, respectively, when only two substituents are present. The lowest possible number given to the substitu-
ent coming 1st in alphabetical order except that when names are based on those of the compounds mentioned in the beginning
ww

of section-E.
CH3
H3C H3C
CH3
H3C CH3
CH3
1-ethyl-4-pentylbenzene 1,4-dipropylbenzene 3,5-diethyltoluene

CH3
CH3
H2C CH3 CH3

CH3 CH3
CH3
4-ethylstyrene p-ethylstyrene 1,2-dimethyl-3-propylbenzene 1-butyl-3-ethyl-2-propylbenzene

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16   Essential Organic Chemistry

Problem 1-15 Write IUPAC names of the following hydrocarbons

I II III IV

4 4

2 2
1 1

m
I II
1,2,.4-trimethyl benzene 1,4-diisopropyl-2-propyl benzene

.co
5
1

ing
1 3
2 3

III IV
ch
1,3-diethyl-2,5-dimethyl benzene 1-cyclohexyl-3-cyclopentyl benzene
oa

1-2G  Naming Halogen Substituted Compounds

Substitutive naming of halogen compounds are formed by adding the prefixes “fluoro-“, “chloro-”, “bromo”- or “iodo”- to the
yC

name of parent compound.

Cl Cl Cl
1 8
M

5 8 6 2 6
6
3
CH3 9 7 5 4 3 1 H3C 7 5 4 3 2
1
H3C 4 2 H3C CH3 CH3
k

Cl Cl Br
pic

3-chlorohexane 3,4,7-trichlorononane 5-bromo-2-chloroctane

If there is a choice between the two halides for numbering, alphabetical order is followed eg,
w.

Br Br I
4
ww

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

1-3  Naming Compounds Containing One or More

Similar Type of Principal Functional Groups
Name of such compound which contain principal functional group ends with suffix of that group provided by IUPAC.
Suffixes and prefixes for some of the common functional group is given in Table-1.2.

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Nomenclature of Organic Compounds    Chapter 1    17

Table 1.2  Suffixes and Prefixes for common functional groups

Class Formula Prefix Suffix
(1) Acid halide —CO—X Halocarbonyl Carbonyl halide
(2) Alcohols —OH Hydroxy -ol
(3) Aldehydes —CHO Formyl Carbaldehyde
—(C)HO Oxo- -al
(4) Amides —CONH2 Carbamoyl Carboxamide
—(C)ONH2 -amide
(5) Amines —NH2 Amine -amine
(6) Carboxylic acid —COOH Carboxy -carboxylic acid
—(C)OOH -oic acid
(7) Ethers —OR Alkoxy
(8) Esters —COOR R-oxycarbonyl R-carboxylate

m
—(C)OOR R-oate
(9) Ketones  (C)==O Oxo -one

.co
(10) Nitrile —CN Cyano -carbonitrile
—(C)N nitrile
(11) Sulphonic acid —SO3H Sulpho -Sulphonic acid

ing
(Formulae containing carbon in parenthesis indicates that the carbon is part of main chain)

1-3A  Aldehydes
ch
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
oa

of the aldehyde group —CHO.

1 1
3 CHO 5 3 CHO
yC

4 6 4 2
H3C 2 OHC
1
CH3CHO CHO H3C 5
7 H3C
M

6
Ethanal Pentanal 4-ethyl-2,5-heptadienal 2-ethylhexandial
k

If the parent chain contain more than two —CHO groups, they are named as carbaldehyde and carbon of —CHO is not
pic

counted in main chain as

CHO CHO
1
w.

4 4 2 6 5 CHO
CHO CHO
1 3
OHC 2 3 CHO OHC 4 2
3 1
ww

Butane-1,2,4-tricarbaldehyde Cyclohexanecarbaldehyde 4-cyclopentylbutanal 3-(formylmethyl) hexanedial

or 3-(2-oxoethyl) hexanedial

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

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17