[J] NOMENCLATURE OF ORGANIC

COMPOUNDS
There are two general ways of naming organic compounds;
(i) Common or trivial and (ii) Systematic names (lUPAC names).
3.1. Trivial Or Common names
During the first half of the nineteenth century, chemists discovered ma ~
new compounds and named them with little or no structural significance. Sue
common or trivial names might reflect the source of the compound, the method of I'
preparation or the name of the person working on it. For example, acetic acid can
obtained from vinegar, it got its name from the Latin word for vinegar, acetu
Formic acid, HCOOH, was so named as it was obtained by distillation of red an
(Latin, formica = ants). Ethylene chloride got its name because it was made by t
reaction of ethylene with chlorine. Barbituric acid is said to perpeturate the name
woman barbara. Some names, refer to distinctive properties that characterize th
compound, e.g; acrolein (Latin acris; pungent); chrysene (Greek chrysos, golden
glucose (Greek glucose, sweet) refer to attributes of odour, colour and taste.
An ordinary name given to a compound without reference to its structure ,
called a Common name or Trivial name. The common names are like nicknames.
Common or trivial names are still widely used by chemists, biochemists an
the companies that sell chemicals. For this reason, trivial names have a firm plac
in the literature and language of organic chemistry and hence it is still necessary t
learn the common names for some of the common compounds.
3.2. Systematic Naming of Organic Compounds by IUPAC System
With the rapid growth of organic chemistry, the number of compounds
increased fantastically (now about 3 million). It becomes impossible to give commo
names to such a large number of organic compounds.
In 1957, the International union of Pure and Applied .chemistry evolved a
scheme for giving systematic names to organic compounds on ~thebasis of structure
This is known as the IUPAC System. The systematic name of a compound derived
from its structural formula by applying IUPAC rules, is referred to its as IUPAC
Name. One organic compounds can have only one IUPAC name. It is superior to a
common name as it gives an insight into the structure of the molecule. Knowing the
IUPAC name of a compounds, we can at once write its structural formula. Remember
that the common names identify compounds while the IUPAC names represent
structures.
The IUPAC system of nomenclature is based upon the following principles for
. assignment of substitutive names.
1. The longest continuous carbon chain (the parent chain) containing the
functional group is the parent structure of aliphatic (acyclic) compounds.
2. The common names of familiar cyclics are frequently chosen as parent
structures of compounds containing cyclic structures.
3. An order of preference is assigned to various functional groups. The groups
higher in the order are given preference in the definition of parent structures.
Some functional groups are always considered as substituents.
.•'OMENCLATURE OF ORGANIC COMPOUNDS 93
Functional Group
A functional group is an atom or group of atoms in a molecule that gives the
molecule its characteristic chemical properties. Double and triple bonds are
functional groups. Other examples include -CI, -Br, -OH, -NH:l, -COOH,~ C = 0
groups.
I
CH3CH2CH2 - CH2
Hydrocarbon portion
+ OH.
Functional group
The concept of functional group is important to organic chemistry for three reasons:
1. Functional groups serve as basis for nomenclature.
C) Functional groups serve to classify organic compounds into classes / families.
All compounds with the same functional group belong to the same class.
3. Functional group is a site of chemical reactivity in a molecule. Compounds in
the same class have similar chemical properties.
Alkyl groups
Radicals which are derived by the removal of one hydrogen atom from an
alkane are called alkyl radicals and are expressed by general formula, CnH2n+1.The
ames of the alkyl groups are derived by replacing the ending-ane of the
corresponding alkane by -yl. An alkyl group is represented by a general symbol R-.
Two different alkyl groups (n-propyl and isopropyl) are derived from propane
epending on whether the hydrogen atom is removed from the terminal or the
middle carbon of propane. Similarly, two alkyl groups are obtained from each of n-
utane and isobutane. Some of the common alkyl groups are given belo~:
•.Iethyl CH3 - Ethyl CH3CH2 -
n-propyl CH3CH2CH2 - I
Isopropyl CH3 - CH- CH3
-butyl CH3CH2CH2CH2 - I
Sec butyl CH3-CH2-CH-CH3

CH3 CH3
I I
sobutyl CH3 -CH - CH2 - tert-butyl CH3- C-
I
CH3
CH3
I
-pentyl CH3CH2CH2CH2CH2 - Isopentyl CH3 -CH - CH2 - CH2 -

CH3 CH3
I I
rt.pentyl CH3CH2- C- Neopentyl CH - C - CH -
3 2
I I
CH3' CH3
alkyl group is known as primary if its carbon of attachment is bonded to only one
er carbon atom, secondary if bonded to two other carbon atoms, and tertiary if
94 ORGANIC CHEMISTRY

bonded to three other carbon atoms. Thus isopropyl group is a secondary alkyl group
but isobutyl group is a primary alkyl group.
Unsaturated hydrocarbon groups are called alkenyl groups, while the
aromatic hydrocarbon groups are called aryl groups and are represented by the
general symbol Ar.
CH2=CH- CH2 = CH --CH2 - -CGH.J- -
Vinyl Allyl Phenylene
C6H5 -CH2- C6H5CH(
Benzyl Benzal
1. Alkanes
Hydrocarbons that contain only single bonds arc called alkanes.
Hydrocarbons are compounds that contain only carbon and hydrogen. The first four
members of the series are known by their common names; methane, ethane, propane
and butane. The names of higher alkanes are derived from the Greek prefixes that
indicate the number of carbon atoms in the molecule. Thus pentane has 5 .carbon~,
.hexane has 6 and so on,
Table 3.1. Names of the unbranched alkanes
Name No. of Structure Name No. of Structure
Carbons Carbons
Methane 1 CH4 Eicosane 20 CH:!\CH~'[hCR!
Ethane 2 CH3CH:1 Heneicosane 21 CH.!!CH2iH)CH:.
Propane 3 CH3CH2CH3 Docosane 22 CH;j(CH2)20CH:1
Butane 4 CH3(CH2)20H3 Triacontane 30 CH:1{CH:L'28CH:J
Pentane 5 CHa(CH2)3CH3 Hentriacontane 31 CH3(CH2 )29CH:l
Hexane 6 CH3(CH2)4 CH3 Tetracontane - 40 CH3(CH2 ):iSCH:3
Heptane 7 CH3(CH2)5CH3 Pentacontane 50 CH;1(CH2),lsCH;
Octane 8 CH3(CH2)6CHa Hexacont •me 60 CH3tCH:,!i,)sCH:!
Nonane 9 CHa(CH2)7CH3 Heptacontane 70 CH:1(CH2)6SCH:1
Decane 10 CH3CCH2)8CH3 Octacontane 80 CHs (CH2 }7R CH3
Undecane 11 CH3(CH2)gCH3 Nonacontane 90 CH:1iCH2)8SCHS
Dodecane 12 CH3(CH2)lOCH3 Hectane 100 CH3(CH2 )gSCH:1
Tridecane 13 CH3(CH2)11 CHa

In the common system all isomeric alkanes have 'the same parent name.
The name of various isomers are distinguished by prefixes. The prefix indicates the
type of branching present in the molecule.

The prefix n-inormal) denotes an unbranched chain of C atoms. The prefix

iso-indicates a CH3 branch on the second carbon from the end. The prefix
nee-indicates two methyl groups attached to the second carbon from the end of the
continuous chain.
·~MENCLATURE OF ORGANIC COMPOUNDS 95

CHa CH'
I .3
I
3 -CH-CH3 CH:3- CH - CH2CHa CHa-CH2-CH~-CH2-CH2
Isobutane Isopentane n - Pentane
CH3 CH:-l
I I
Ha -C-CH:l CH;l - C - CH 2CHa CH:1
I I I
CH3 CH:1 CH:1 - CH - CH2CH:!CH:1
Neopentane Neohexane Isohexano
'ACRules for Naming Alkanes
The IUPAC system is much the same fOI' all classes of organic compounds.
ranched-chain alkanes are named according to the' following rules:
Find the> longest continuous carbon chain in the molecule and name the
alkane corresponding to this number of carbon atoms.
Number the carbon atoms of the longest chain starting from that end so as to
assign the lowest possible total number to the substituents. If there are more
than one longest chain, select the chain with greatest number of substituents.
The position of each substituent is specified by the number of carbon to which
it is attached in the longest continuous chain.
When two or more substituents are present on the same carbon, use the
number twice
When two or more substituents are identical, indicate this by the use of
prefixes di -, tri -, tetra -, and so on.
The substituents are written in alphabetical order before the parent name.
Each substituent is -prefixed by the number assigned to it and separated
from the name by a hyphen. If several identical radicals are present, their
numbers are listed together, separated each number by commas. Some
examples are given below to illustrate the system.
CH3
CH3
I
lCH3 _2C-3CH2 -4CH2uCH3
1CH3 - 2CH2 - 3t -
I
4CH2 5CH2 6CH3
I CH2
CHa I
CH3
2,2 - dimethylpentane
3 - ethyl 3 - methylhexane

CH3CH3
I I
CH2CH2CH3
I I I
CH3 -7CH2 -6cH2 _5C - C -3CH-2CH2-CH3 7CH3 - 6cHz - uCH - 4CH - 3CH - 2CH -lCH3
I I I I I I
CH3CH2 - CH3 CH3 CH2 CH3 CH3
4, 4;,5· Triethyl ·3,,5-dimethyloctane I
~'H
) 2
CH3
2,3,5 -trimethyl-4 -propylheptane
96 ORGANIC CHEMISTRY

2. Cycloalkanes
Cycloalkanes with only one ring are named by adding the prefix cyclo- to the
name of the alkane having the same number of carbons as in the ring. Cycloalkanes
are often represented by simple geometrical figures. It should be noted that each
corner represents CH2 group.
Substituted cycloalkanes are named as alkyl cycloalkanes. The substituents
on the ring are named, and their positions are indicated by numbers. The ring is
numbered so that the substituents are given the lowest possible numbers.
The ring is designated as a substituent if the alkane chain contains a greater
number of carbon atoms than the ring. .

C3H3

/C{I2
H2C-CH2
Cyclopropane
4

5 O
6
2

ICH2CH3
l-ethyl-3-methylcyclohexane
~CH2CH2CH2CH3
l-cyclopropylbutane
CH3 -CH-CH3

V
CH3CH2CHCH2CH3 Ct)3 3
1

5
4
3-Cyclopropylpentane
CH3-C-CH3 1,1-Dimethylcyclopentane
I
CH3
4-tert-butyl-l-isopropyl-2- methylcyclohexane
Bicyclic Compounds. Polycyclic compounds, in which two or more carbon atom
are common to two or more rings, take the name of an open chain compound having
the same number of carbon atoms, and suffixes such as bicyclo- and tricylo indicate
the number of rings. The points of fusion of the rings are indicated by listing the
number of carbon atoms in each of the bridges. The bridges are listed, within
brackets, in order of decreasing length. The numbers in brackets indicate how many
atoms are in each bridge.
Numbers are assigned to the carbon atoms by beginning at a bridgehead and
moving along the bridges. The longest bridge is numbered first, the second large
next and so on.
Bridgehead r
4~7

3~8
One-carbo!!,_~_~/CH
bridge {c
rfHu>
27
Two carbon I CH I
I
6H 2 } .
Two carbon
bridge 5
CH21 2 3CH2 bridge
2
Bicyclo [4,2,0] octane CH/
~ Bridgehead
Bicyclo [2,2,1] heptane
 AENCLATURE OF ORGANIC COMPOUNDS 97
alkanes: A "spiro union" is one formed by a single atom which is the only
on member of two rings. A "free Spiro union" is one constituting the only union
t or indirect between two rings. The common atom is designated as the "spiro
". According to the number of spiro atoms present, the compounds are
tinguished as monospiro-, dispiro-, trispirocompounds, etc. The following rules
y to the naming of spiroalkanes containing free spiro unions.
Monospiro compounds consisting of only two alicyclic rings as components are
ed 'by placing "spiro" before the name of the normal acyclic hydrocarbon of the
e total number of carbon atoms. The number of carbon atoms linked to the spiro
m in each ring is indicated in ascending order in brackets placed between the
o prefix and the alkane (hydrocarbon) name. The carbon atoms in monospiro
nes are numbered consecutively starting with a ring atom next to the spiro
m, first through the smaller ring (if such be present) and then through the spiro
m and around the second ring.
}--"V-. 2 4 1
(;C)
~ 9 10 4 3
rN 5 2
piro [4.5] decane Spiro [2.2] pentane Spiro [3.3] heptane

KHA
~
7 8
7\-N2
8 9 3
d)"
piro [2.5] octane 5-methylspiro[3.5]nonane l-methylspiro [3.5]nonane
10 9 7 5 4
Polyspiro compounds consisting of a linear
11~3
embly of three or more alicyclic systems are named
placing "dispiro-", "trispiro-" "tetraspiro-" etc.,
12~W7\-{
13 1416 17 1 2
ire the name of the unbranched -chain acyclic Dispiro [5.1.7.2] heptadecane
rocarbon of the same total number of carbon
ms. The numbers of carbon atoms linked to the spiro atoms in each ring are
icated in brackets in the same order as the numbering proceeds about the ring.
- mbering starts with a ring atom next to a terminal spiro atom and proceeds in
h a way as to give the spiro atoms as low numbers as possible after numbering all
carbon atoms of the first ring linked to the terminal spiro atom.

Alkenes
Trivial or Common System. In this system of nomenclature alkenes are
ed by replacing the ending -ane of the corresponding alkane by -ylene, e.g.,
ylene from ethane, propylene fron. ~:'~pane and isobutylene from isobutane
CH3
I ,
CH2 = CH2 CH3 -CH = CH2 CH3 -C = CH2
Ethylene Propylene Isobutylens
98 ORGANIC CHEMISTRY

The use of trivial names becomes difficult for individual alkenes having four
or more carbon atoms because of the large number of isomers possible. So the
common names are used only for the above three alkenes. However, a few simple
alkenes may be named as derivatives of ethylene, e.g.,

CHaCH = CH2 CH3CH = CHCHa (CHa)2C = CH2

Methylethylene sym-Dimethy lethylene unsym -Dimethylethyiene

A few special trivial names are also in common use, e.g.,

C(jH5CH = CH2 C(jH[iCH = CHC()H~
Styrene Stilbene

(Ii) IUPAC System. 1. Select the longest continuous chain containing the
carbon - carbon double bond as the parent chain which is then named by
replacing the ending -ane of the corresponding alkane by -ene.
2. The parent chain is numbered starting from the end nearer to the double
" bond."
3. The position of the double bond is indicated by putting the number of lower
numbered carbon of the double bond before the name of the alkene.
4. Presence of more than one double bond is indicated by the suffix -diene for
two double bonds, -triene for three double bonds and so on.
5. Indicate the locations of the substituent groups by the number of the carbon
atoms to which they are attached.
6. For cycloalkenes, numbering is always started frOTI1 one of the carbon atoms
of the double bond such that when continued toward the other carbon of the
double bond, the substituents (if any) are given the lowest sum of numbers. It
is not necessary to specify the position of the double bond (unless there are
more than one double bond in the ring) because it is always 1.
When a geometric isomer is to be specified, 3 prefix cis or trans i
added.

CHs CHa
CHa 51 '1 aCH 21 1
I CHaCH2 - C -- CH2 - 2 - C = CH2
CHa -C=CH-CHa 8 7 6 I
2 -?A:ethyl- 2 - butene CHa CH2 CH2
5 - Ethyl- 2,5 -dimethyl -1- octene

CR3 CH2CH2CH3
I I
CH3 -CH -CH CH CH -= CH2 ICH.) =2C-aCH =.c4CH2
I - I
CH3 en,
4,5 -Dimethyl- 3 - prupyl - 1 hexene 2 -methyl-1,3 - butadiene
 ATURE OF ORGANIC COMPOUNDS 99

6A,
SV 4
-Methylcyclohexene
3
C2HS
D~
5-Ethyl-3-methylcyc1ohexene

C113<:I12 H
'\ /
CH3 - C = C - CH3 C==C
I ~ H/ 'CH21
H H·
cis -2- butene trans-l-Iodo-Z-pentene
H.,C,...
- I/CH - CH" - Cll = CH.., Cl L, - Cll ;= C - Cl l-, (11 = ell"
H2C - ~ . 1-
3-Cycl0propyl-l- propene CH3CHCH2Cl12CJ 13

4-( l-Methylbutyl)-l ,4- hexudiene

are a few important alkenyl groups for whichf.rivial (common) names are
ferentially in place of systematic n<:tmes;These are
CH:.!==CH- CH·1-CH ==CH- CH2 = CH - CH2 -
Vinyl Propenyl Allyl
Ethenyl) (I-Propenvh t2-PropenylJ
CH3
I
CH2= CH- CH3CH ==CHCH:2 -
Isopropenyl Crotyl
(I-Methylethenyl) (2 - Butenyl)
Alkynes
Hydrocarbons that contain a carbon - carbon triple bond are called alkynes.
imp lest alkyne, HC == Cll is commonly called acetylene.
The simple alkynes are named in the common system as derivatives of
ene.
CH:~- C CH = C6H5 - C == (' - C6H5 H3C - C == C - CH3
Methylacetylene diphenylacetylene dimethyl acetylene
IUPAC rules for naming alkynes are analogous to those for alkenes.
Select the longest continuous carbon chain containing the triple bond as the
parent chain which is then named by replacing the ending -ane of the
corresponding alkane by - yne.
Number the parent chain from thp end nearer to the triple bond.
Indicate the position of the triple bond by putting the number of lower
numbered carbon of the triple bond before the name of the alkyne.
Alkyl groups and other substituents are numbered, named and placed as
prefixes in alphabetic order.
100 ORGANIC CHEMISTRY

(v) Alkynes containing two triple bonds are named as alkadiynes.

(vi) If both double and triple bonds are present in a molecule, the double bond
takes precedence over the triple bond, then the hydrocarbon is named as an
alkenyne, alkadienyne, alkendiyne, etc., depending on the number of double
and triple bonds in the molecule. The numbers to the multiple bonds are
assigned in such a way that the total of the number remain as low a~
possible.
CH3 CH3
5CH3 - 4CH2 -3CH ~2C =1 CH I I
I CR3 -CH-C = C-C-CH3
CH3 I
CH
3-Methyl-1-pentyne 2,2,5- TrimetI1yl-3-hexyne
5
H C ==~-3CH22CH =1CH2 CH3CH= CH-C== C-C== CH
L-Penten-d-yne 5-Hepten-1,3-diyne

CH3
I
CH2 = CH-CH-C= C-CH = CH2 CH ==C - CH2CH2 - C = C - CH3
5 -Methyl-1,6 - heptadiene - 3 -yne 1,5 - Heptadiyne
CH3 - CH = CH - C ==CH CH3 - C ==C - CH = CH2
3-Penten-1-yne 1-Penten-3-yne
5. Aromatic Hydrocarbons
The nomenclature of the aromatic hydrocarbons and their derivatives is more
complex than that of the aliphatic compounds. The system used for naming the
benzene derivatives generally depends on the number of substituents on the benzen
ring.
1. Monosubstituted- benzene derivatives are systematically named as one wore

6 6
by combining the name of the substituent as a prefix with the word benzene, e.g.,

OCR3
Ethylbenzene Nitrobenzene Bromobenzene
A number of monosubstituted benzene derivatives have common name
which are currently accepted. The IUPAC names are given in brackets.
OR

0 6 6
3

ToIuene
(Methylbenzene)
6
Phenol
(Hydroxybenzene)
Aniline
(Aminobenzene)
Anisole
(Methoxybenzen
 .;OMENCLATURE OF ORGANIC COMPOUNDS 101

6 CH,
6-
CH3
I
CHJ
6 ·6 HJ

Styrene Cumene Benzaldehyde Acetophenone

Pheny lethy lene) (Isopropy lbenzene)

H H

6 6
enzoic acid Benzenesulphonic acid
Sometimes, it is more convenient to name the benzene ring as a substituent, the
henyl group, C6H5
OCHPH
C6HSC=CH <O>-CH,CH,CHO
Phenylacetylene 2-Phenylethanol 3-Pheny lpropanal

Another common aromatic substituent is Benzyl group which is abbreviated as

e
C6H5CH2-·

6-
e
C1

6
e

d = C6HsCH2- - PhCH2-

Benzyl chloride Benzyl

2. In disubstituted benzene derivatives, the relative- positions of the

substituents in the benzene ring are indicated by the numbers allocated to the
carbon atoms of the ring to which the substituents are attached or by using the
prefixes ortho (o-), meta (m-), and para (p-) for the 1,2-, 1,3-, and 1,4- substituents,
respectively. For example,
Cl

rQr 4
1,2-Dichlorobenzene
or .
6Cl
1,3-Dichlorobenzene
¢ CI
r

or 1,4-Dich lorobenzene
a-Dichlorobenzene m-Dichlorobenzene or
) p- Dichlorobenzene

..,...
.
102 ORGANIC CHEMISTR

If th~ two substituents are different, both are used as prefixes successively 1

alphabetic order. The whole name is used in one word.

OCI
2-Chloron itrobenzene
or
OCI
3-Chloroiodobenzene
or
Q Br
o-Chloronitrobcnzene m-Chloroiodobenzene 4-Bromonitrobenzene
or
p- Bromonitrobenzene
If one of the substituents is such that it gives a special name to the molecul
then the special name is used as the parent name, the disubst.ituted compound
named as a derivative of that parent, e.g.,

06N0
NO
2
2
3-Nitrophenol
or
2-bromoanisole
or
4-Nitrotoluene . m-Nitrophenol o-bromoanisole
or
p-Nitrotoluene
If both substituents are such that they independently give a special name :
the molecule, then the substituent which is normally treated as suffix gives t!
parent name to the molecule.

¢ ¢JH ¢
NH2 OH OCH3
4-Ammophenol 4-Hydroxybenzoic acid 4-Methoxybenzaldehyde
or or
p-Aminophenol p-Hydroxybenzoic acid p- Methoxybenzaldehyde
COOH
¢H3
OJ ?\,j~2
-l-Aminobenzoic acid
ON0 or
m-Nitrobenzenesulphonic acid
2
3-Nitrobcnzenesulphonic acid CH3
p-methylanisole
or
I,-Allllllobenzoic acid
Some disubstituted benzene derivatives also have special names t
I ('jJ,-CS(!l1tthe benzene ring together with both the substituents, e.g.,
 CLATURE OF ORGANIC COMPOUNDS 103

0H
6
o-Xylene
CH3

6CR3
m-Xylcne
Q 6
CH3 Catechol
p-Xylene

60H
Resorsinol
0]
OH
6 6
Sa] icylaldebyde
0H
o-Toluidine
CH3

Hydroquinone
o
6~H2
Anthranilic acid
6CHJ
Cresol
o o
Quinol
OCOOH

VCOOH
Phthalic acid

Polysubstituted Benzenes. When three or more substituents are attached to the

benzene ring, numbers must be used to designate their positions. If all the
substituents are the same, the benzene ring is numbered so as to give the lowest
total of the numbers assigned to the substituents, e.g., -,

¢CI CI

CI
1,2,4- Trichlorobenzene
BbB'
1,3,5- Tribrornobenzene

If one of the substituents gives a special name to the molecule, then only the
remaining positions of substituents are mentioned.
CH3 OH
02NON02 B'(J(
NH"

IIOOCONH,
N02 Br
2,4,6- Trinitrotoluene 2,4,6- Tribromophenol 3,5-Diaminob~n/oic acid

Some Polysubstituted benzene derivatives also have special name-s.

+
104 ORGANIC CHEMISTRY

OOH
OH OH

060H
Phloroglucino 1
H3C 6
Mesitylene
CH3 OH
Pyrogallol .
C~CH3
CH
3
Durene
CH3

Polynuclear Aromatic Hydrocarbons

Polynuclear aromatic compounds have more than one benzene nng
Biphenyl, C6HS- C6Hs, and triphenylmethane, (C6H5)3CH, have isolated
rings. Benzene rings sharing 2 ortho carbons are fused or condensed ring
system. •
Isolated ring systems. The following are the important compounds 0
isolated ring systems.

Biphenyl p- Terphenyl Diphenylmethane

The numbering system in biphenyl is:

OOCI O (0)1 (0) (CH3hN-<Q>--O-N(CH31:

3-Chlorobiphenyl 2-Chloro-3-nitrobiphenyl p,p'-di{N,N-dimethylamino)bipheny

Fused or Condensed ring systems. Naphthalene, anthracene and phenanthren

are the most important members of this class, in which the benzene rings are fus
together at ortho positions so that the adjacent rings have a common carbon-carbo
bond.

8 9
7~2
2
6~~3
5 4 5 4
5 10 4
Naphthalene Anthracene Phenanthrene
In the IUPAC system of nomenclature, numbers are assigned only to tho-
positions of the fused ring aromatic hydrocarbons at which substitution can ta·
place as shown in the above structures.
 3CLATURE OF ORGANIC COMPOUNDS 105
The substituted naphthalene derivatives are usually designated by the
es a- and r~-.
The numbering system begins with number 1 at the U.- position.

06
a-Naphthol
OOCOOH
p-Naphthoic acid
OONH2
p-Naphthylamine

roll
l-Naphthol 2-Naphthoic acid 2-Naphthylamine
NO ..•

00 N02
.5-dinitronaphthalene
n-naphthalenesulphonic acid
1-naphthalenesulphonic acid
00
n-naphrhuldehyde
l-naphthaldehyde

HOO
-Bromo-8-methoxynaphthalene o
0, ...
0

9,10-Anthraquinone

9,10-Dihydroanthracene 9,10-Dihydrophenanthrene 2,9- Dimethylanthracene

Br

Br
9,10- Dibromoanthraccne

6. Alkyl Halides

Monohaloalkanes are usually called alkyl halides and they contain

carbon-halogen bonds. They are classified as primary, secondary, or tertiary,
depending upon whether the halogen atom is bonded to a primary, secondary, or
tertiary carbon atom. Abbreviations for these terms are 1°,2°, and 3° respectively.
The common names of alkyl halides are obtained by naming the alkyl group
attached to the halogen and adding the name of halide corresponding to halogen as a
separate word.
106 ORGANIC CHEMISTRY

CH3CH2Br CH3CH2CH2CH2Br I CH3

I I .
Ethyl bromide n-Butyl bromide CH3 -eH-CH3 CH3 -CH-CH2 -Br
Isopropyl iodide Isobutyl bormide
CH3 CH3
I I
CH3 -C-Br CH3 -C-CH2-1
. I I
CH3 CH3
tert. Butyl bromide ~eopentyliodide
Dihaloalkanes are named according to the relative positions of the halogen atoms.
If two halogen atoms are attached to the same carbon atom, i.e. in the germinal
(gem-) position, it is named as an alkylidene dihalide. If the two halogen atoms are
on adjacent carbon atoms, i.e., in the vicinal iuic-) position; it is named as a dihalide"
of the alkene from which' it may be prepared by the addition of halogen. If the
halogen atoms are on the terminal carbon atoms of the chain it is named as the
polymethylene dihalide.
For example,
Br Cl
I I
CH3 ~CH-·Br CH3 ~C-CH3 Br - CH2 - CH2Br
Ethylidene dibromide . I Ethylene dibromide
Cl
Isopropylidene dichloride
CI
r
H3C-C-CH2Cl Cl - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - Cl
I Hexamethylene dichloride
eH3
Isobutene dichloride
IUP AC System: The IUPAC names of alkyl halides are obtained by using the
following rules:
1. Select the longest chain to which the halogen is attached and give it the nam
• of the corresponding alkanes.
2. Prefix the name of alkane by halo; i.e., chloro, bromo, iodo or fluoro.
3. Number the chain so as to give the carbon carrying the halogen atom th
lowest possible number.
4. Other substituents are numbered, named and placed as prefixes in alphabeti
.
order. For example

Br ·CH Br
I I 3 .I
eH3 -CH-CR3 CH3 - CH2 - CH - CH2Cl CH3 - CCR2 - Br
2 - Bromopropane 1- Chloro - 2 -methylbutane I
CR3
1,2 - Dibromo ~~ - methylpropane
 MENCLATURE OF ORGANIC COMPOUNDS 107
CI' I
I I
Hs - CH2 - C - CH2CH2Br CI- CH2 - CH - CHCH2CH2 - Br
I I
CI . CHs
~- Bromo - 3,3 - dichloropentane 5 - Bromo -1- chloro - 2 -iodo - 3 - methyl pentane
Organometallic Compounds
Organometallic compounds are named as alkylmetals.
CHsCH2Li (CHsCH2)4Pb
Ethyllithium Tetraethyllead
If the metal is bonded to an inorganic anion as well as a carbon atom, the
compounds is named as a derivative of the inorganic salt.
CHs
I
CH3CH2MgBr HsC-C-MgBr
Ethylmagnesium bromide I
CHs
tert·· butylmagnesium bromide
8. Alcohols
Common System: In this system alcohols (R-OR) are named by naming the
alkyl group attached to the -OR group and adding alcohol as a separate
word.
CHs CHs
CHsCH2CH20H I I
n - propyl alcohol CHsCHOH CHs -,CH - CH20H
Isopropyl alcohol Isobutyl alcohol
on, CRs CHs
I I I
CHsCH2 - CHOH CH3-C-OH CHs-C-CH20H
sec - Butyl alcohol· I I
Clls CHs
tert - Butyl alcohol Neopentyl alcohol
The positions of the other substituents in the alkyl groups are indicated by the
Greek lettersoralpha), j3(beta), y(gamma), and 8(delta). The carbon atom bearing the
hydroxyl group is named as a, next carbon atoms named as ~,y,8 and so on
respectively. .
Y
CI- CH2 _BCH2 _aCH2 -OH BrOlCH2liCIi2YCHlcH2aCH20H
y-Chloropro~yl alcohol U)- Bromoamyl alcohol • .
An alcohol, C5HllOH containing five carbons is commonly called amyl alcohol and
the end carbon is generally named as w(omega).

IO
n ~ Br
CH2-CH3 I .
. I CH3 - CHCH2CH20H ,
[) OH . . y.Bromobutyl alcohol
c-phenylethyl alcohol
108 ORGANIC CHEMISTRY

IUPAC System: l.Select the longest carbon chain containing the hydroxyl group as
the parent alkane.
2. The name is obtained by replacing the ending -e of the name of the parent
alkane by -01. Thus, the alcohols are named as alkanols.
3. The position of the hydroxyl group is indicated by the number of the carbon
attached to the -OH group, and is written before the name of the alkanol.
4. Other substituents are numbered, named and placed as prefixes in alphabetic
order.
CH~CH2CH:3 OH
I I
CH3CH;lCH20H CH;~CH2- C - OH H2C = CHCHCH:1
1-propanol I 3-Buten-2-o1
CH2CH3
3 - Ethyl - 3 - hexanol
Note that in IUPAC system the OH is given a lower number than C = C or Cl.
Br
I
CI- CHCH;lOH CH;19HCH9HCH2CH3
I
CI CH3 OH
2,2 - Dichloroethanol 4 - Bromo - 5 - methyl - 3 - hexanol
Diols and Triols have both common and IUPAC names. The IUPAC names are
obtained by adding the suffix diol or triol to the name of the parent alkane
containing two or three -OH groups respectively. The positions of the -OH groups
are indicated by the numbers. For example
CH20H CH.)OH CH20H
I . W

I I
CH20H CH;l CHOH
I I
1,2 - Ethanediol CH20H CH20H
(Ethylene glycol) 1,3 - Propanediol 1,2,3 - Propanetriol
(Propylene glycol) (glycerol)
9. Phenols
Compounds containing an ·-OH group attached directly to an aromatic ring
are called Phenols. Phenols are usually named by common system or as derivatives
of the parent phenol, C6H50H which is called hydroxybcnzene. Their systematic
names are also given in parentheses.
OH

o
Phenol
(Hydroxybenzene)
6
o-Cresol
(2-Methylphenol)
CHJ
HO~<O>-N02
p- N itrophenol
(4-Nitrophenol)
 O~lENCLATURE OF ORGANIC COMPOUNDS 109
OH .
OOH OOH HO-(O)-OH'
Hydroquinone
Catechol Resorcinol
(p- Dihydroxybenzcne)
0- Oihydroxy benzene) (m- Di hydroxybcnzene)

OH OH
02N¢N02 Ho6oH H0lQr0H
N02 Pyrogallol 01-1
(] ,2,3-Hydroxybenzene)
Picric acid Phylorcglucinol
(2,4,6- Trinitrophenol) (1,3,5- Trihydroxybenzene)

0H
6
Salicylaldehyde
(o-hydroxybenzaldehyde)
OCH)
m-Cresol
(m-hydroxytolucnc)
6
Salicylic acid
(o-Hydroxybcnzoic
COOH

acid)

While naming the polvfunct ional aromatic compounds, the hydroxy function
is usually placed low in order precedence; only the' amino and the ether functions are
placed lower than the hydroxy function.

HO-OCOOH CH)O-(O)-OH HO-(O)-NHCOCH 3

p-hydroxybenzoic acid p-M{;(hoxyphenol p-Hydroxyacctanilide

Compounds with the hydroxyl group attached to a polycyclic benzenoid ring
system also belong to the phenol faimly and they are named in a similar ways;
OH HO
~ ~OH

~ ~
a-Naphthol 2-Anthranol 9- Phenanthrol
(1-1 lydroxynaphthalene) (z-Hydroxyanthrancene) (9- Hydroxyphenanthrene)

10. Ethers

Common system. In the common system, the names of ethers are derived by
naming the two alkyl groups attached- to the oxygen atom, in alphabetic order,
followed by the word ether. If the groups are same, the prefix di- is used with the
group.
ClH;'jOC2H5 CH:lCH:zOCH:1 (CH:3)2CHOC2H5
Oiethyl ether Ethyl methyl ether Isopropyl ethyl ether
] 10 ORGANIC CHEMISTRY

(CH3)3COC2H5 CH2 = CHO CH = CH2· C6H5CH20CH2C6H5

t - Buyl ethyl ether Divinyl ether Dibenzyl ether
In the IUPAC system, ethers are .named as Alkoxyalkanes or compounds
containing a functional group of higher priority than ether.
CH3CH2CH20 - CH3 C6H50CH2CH~ (CH3)2CHOCH(CH3)CH2CH3
l-~ethoxypropane Ethoxybenzene 2-isopropoxybutane
CH3
I
CH3CH2CH2CH2CH20 - CHCH20H
Methoxycyclohexane 2 - Pentyloxy -.1-propanol

11. Oxiranes (Epoxides)

Oxiranes are cyclic ethers in which the ether oxygen is part of the three
membered ring. Oxiranes are also called epoxides. Because they are readily
prepared from alkenes, they are commonly known as alkene oxides. In the IUP AC
system, they are named as alkyloxiranes. Substituents on the oxirane ring require
a numbering system. The oxygen atom is given the number 1.

/0"
H2C-CH2
/0"
CH3CH-CH2
°
/\
H2C-C(CH3h
Oxirane 2-Methyloxirane 2,2- Dimethyloxirane
(Ethylene oxide) (Propylene oxide) .,: (Isobutylene oxide)
-1-.,

12. Aldehydes and Ketones

Aldehydes. The common 'name. Th'e common names of aldehydes are derived
from the names of the corresponding acids by replacing the suffix -ic (or -oic) acid
by aldehyde. Locations of substituent groups are designated by Greek letters U-, B-,
y- and so on, beginning with the carbon next to carbonyl group.

CH3CHO
Acetaldehyde
(from acetic acid)
Benzaldehyde
(from benzoic acid)

IUPAC System. In the IUPAC system, aldehydes are named as alkanals.

Select the longest chain containing the aldehyde group and replace. the final
-e from the name of the corresponding alkane by the suffix -al. The C of CHO is
number 1. Since the aldehyde group is always at the end of the chain, there is no
need to indicate its position. However, the positions of the substituents are indicated
by number, named and placed as prefixes in alphabetic order. .
. When there are two aldehyde groups in a molecules it is named as
.Alkanedial. Notice that -e of the corresponding alkane name is retained.
 CLATURE OF ORGANIC COMPOtJNDS 111

CH3 0 CI 0
I" , I "
CH3 - CH - CH2 - C - H CH3CH2CH2CH - CH
3 -Methylbutanal 2 - Chloropentanal

,
oII 0
II
Br
I
0'
II
H - C - CH2CH2CH2CH2- CH CH3CHCH2- C...:.H
1,6-Hexanedial 3-Bromobutanal
en -CHO group is used as substituent, it is named as a formyl group.

5~HO
o-Formylbenzoic acid
6CHO
2-Formylcyc1ohexanone
etones. Common' name. The common names of ketones are obtained by naming
!Ikyl groups attached to the carbonyl group separately in alphabetical order and
dding the word ketone. For symmetrical ketones the prefix di- is used. The
sitionsof the substituents are indicated by the Greek letters as in the case of
dehydes.
9 9
CH3CH2 - C - CH3
~ ~1 9 'Ir'
CHf:::H - C - ~H2CH2CI
CH3 -C-CH3
Dimethyl ketone Ethyl methyl ketone a,pt -Dichlorodiethyl ketone
(Acetone)
o o
<O>-~CH3
Methyl Phenyl ketone
<O>-~-<O>
Diphenyl ketone
(Acetophenone) (Benzophenone)
The ketones in which the carbonyl group is attached to a benzene ring, are
named as -phenone, as shown above in parentheses.
In the WP AC System the names of ketones are derived from the names of
the corresponding alkanes by replacing the ending -e with -one. The position of the
, .
keto group is indicated by numbering the parent chain from o.ie end so that the
carbonyl group gets the lowest possible number. The substituents are numbered,
named and placed as prefixes in alphabetic order.
When there are two .carbonyl groups in a molecule, it is named as
Alkanedione.
CH30
CH3
9
- C - C~CH3
T II
CH3 - CH - C - CH3 H2C = CHCOCH3
~,

Butanone 3-Methyl-2-butanone 3-Buten-2-one

112 ORGANIC CHEMISTRY

o
II
CICH2CH2CCH3
OR OR
. 4-chlorobutanone COCH3 COCH2CH3
4-Acetylbenzoic acid 4-propanoylbenzene
sulphonic acid
Sometimes a carbonyl compound also contains a more important functional
group. In such cases, the prefix oxo-, along with a number indicating its position in
the chain, is used for the carbonyl group.
o
II
CH3CH2 C CH2CHO
3-0xopentanal
The general order of precedence of the functional group in naming the compound is:
acid anhydride > carboxylic acid > sulphonic acid > ester > acid halide > amide >
aldehyde> ketone> alcohol e phenol> ether> amine
The C=O group has numbering priority over the C=C group.
13.' Carboxylic acids
Common or trivial names. The common names of the carboxylic acids are
usually derived from the Latin or Greek words that indicate one of their original
source. All common names of acids end in -ic acid. Common names, such as formic
(ant) and butyric (butter) acids, are based on the natural source of the acid. The
positions of substituetnt groups are shown by Greek letters a, /3, t, 8, etc. The carbon
atom adjacent to the carboxyl carbon is assigned the letter a . the next carbon on the
chain /3, the next one y, and so on. Some common names of carboxylic acids are given
below:
CH3COOH ' CH3CH2COOH CH3CH2CH2COOH
acetic acid Propionic acid Butyric acid
CH3(CH2)4COOH (CH3)3CCOOH (CH::!)2YCHf1CH/CH2COOH
Caproic acid Pivalic acid y-methylvaleric acid
CH3(CH2)3COOH CH3(CH2)14 COOH CH3(CH2 )lGCOOH
Valerie acid Palmitic acid Stearic acid
C6H5COOH 0- HOC6H4COOH C6H5/CHlcH~t:CH~COOH
Benzoic acid Salicylic acid y-Phenylbutvric acid
'ClOH7COOH CH3(CH2)8COOH (CH3)2C(OH)COOH
Naphthoic acid Capric acid cc-Hydroxyisobutyric acid
Some carboxylic acids have names derived from acetic acids, e.g.
(CH3)3COOH C6H5CH2COOH (CH3)2 CHCH2COOH
Trimethylacetic acid Phenyl acetic acid Isopropylacetic acid
 l'lCLATURE OF ORGANIC COMPOUNDS 11:3
The four simplest of the dicarboxylic acids are known exclusively by their
on names.
HOOC-COOH HOOC - CH2COOH
Oxalic acid Malonic acid
HOOC --<CH2 )2COOH HOOe - (CH:d):l ..COOH
Succinic acid Gluturrc acid

;PAC System. In the IUPAC syste-m, the name of the carboxylic acid IS obtained
om the chain of carboxylic acid, by replacing the ending -l' of thr- corresponding
kane by -oic acid. The positions of the substituents are mdic.ucd .by numtx-rs.
The carboxyl carbon is always given number 1, the carbon .uljacent to It is given i!)I.·
umber 2, and so on.
HCOOn CH;3COOH CH:JCH/"OOH
Methanoic acid Ethanoic acid Propanoic acid
Br CI·L 011
I i " I
CH::!CH2CH2COOH CH3-CH-COOH CH:~CHCH elf (:HCOOH
Butanoic acid 2 - Bromopropanoic acid 2 - Hydroxy - 5 - methyl- 3-
hexenoic acid

CH3C = CCH2CH2-COOH (0)- CH2 - ~H - CH2 - CH2 - COOH

4-Hexynoic acid ,0''
-l-chloro-c-phcnylpentanoic acid
It IS not convenient to name a cychc c;'J'bm_,\ 1:( 'w:cl b:. It r1'.\(' :-;y"t('ll'.
how ever. occasionally they »re named as carboxyhc .uid s. e, ~1"

(O)-COOH OC)OH
Benzene carboxylic acid Cyclohcxanecarboxylic acid
The common names acceptable in the JUPAC svstem are acetic acid and
benzoic acid, although most of the common names ,1n- "I dl ) II UFt.'
Dicarboxylic acids are name-d by adding the :,;ufT1X-Jioic ann the word acid
to the longest chain with the two COUH's.
OH
I
HOOC-·CH~CH2CH~CH~COOH HOOC - CH~ _.C'H ~OO,r-I
1,6 - hexanedioic acid :2- Hyd roxybutancdioic acid
Aromatic carboxylic acids are usually num.-d as derivatrves of benzoic acid, e.g.

AOCOO~H3 :Ao
COOH
. Br{5H
~ ,
+-Methylbenzoic acid
~CHO
m-Formylhenzoic acid 2 Bromo-5-nitrobenzoic
VN0 2
acid
 114 - ORGANIC CHEMISTRY
-
The names of some important acids are given below. Their common names
are given in parentheses.

5~H 5~OH OOH

2-Hydroxybenzene Benzene-l,2-dicarboxylic acid Naphthalene-I-carboxylic acid
carboxylic acid (phthalic acid) (a-Naphthoic acid)
(Salicylic acid)
Derivatives of Carhoxylic Acids
14. . Esters
- The names of esters are derived by writing the name of alkyl group of the
alcohol, followed by the name of the acid with the ending -ic acid replaced by -ate.
This nomenclature applies to both common and IUPAC names of esters.

Formula Common Name IUPAC Name

o
II Methyl formate Methyl methanoate
H-C-OCH3
-0
II Ethyl acetate Ethyl ethanoate
CH3 - C - OCH2CH3
o
CH3CH2CH2 _g - OQH3 Methyl butyrate Methyl butanoate

CH
1 3 O~ , Met hvl i butyrate
Y ISO Met h yI iso butanoate
CH3 -CH- -OCH3
If the ester function (-COOR) is to be treated as a substituent, it is treated as a
carboalkoxy group.
C2HsCOOCH2CH2CH2COOH
4-Carboethoxybutanoic acid
15. Acid Halides
Acid halides are the derivatives of carboxylic acids in which the -OH 0
carboxyl group has been replaced by a halogen atom.
Acid halides are named in both the common and IUPAC systems by droppi
the ending 'ic add' from the name of the parent acid and adding the suffix '- .
halIde'. .
Formula Common Name IUPACName
CH3COCI --~--------------~--~~~~~-------
Acetyl chloride ' Ethanoy 1chloride
CH3CH2COCI Propionyl chloride Propanoyl chloride
o
,<O>-~-Cl
....
r'~
Benzoyl chloride
 TURE OF ORGANIC COMPOUNDS 115
.d Anhydrides
.•.u:id anhydrides are the compounds which are obtained after the elimination
er molecule from the carboxyl groups of two carboxylic acid molecules (or
e two carboxyl groups 'ofdicarboxylic acids). '
Acid anhydrides are named by replacing the word 'acid' in the name of parent
. 'anhydride'. For mixed acid anhydrides, the parent name of each acid is '

o-~'~~O
._ en in alphabetical order, followed by the word anhydride. '
oII
0
II
oII 0
II
_ -C-O-C-CH3 ~C-O-C~ H-G-O-C-CH3
eetic anhydride Acetic formic anhydride
.<"r..1.--oic anhydride)
Benzoic anhydride

Amides
Amides are the compounds in which -OH of the carboxyl group ,has been
ced by an amino group, - NH2.
Simple amides are named by replacing the ending '-ic acid' (Common) or -oic
IUPAC) by the word 'amide'. The IUPAC names are given in parentheses.
oII 0
. II
CH3 - C - NH2 C~3CH2 - C - NH2 CH3(CH2)4CONH2
AcetwrnUde PTopio~de Caproamide
(Ethanamide) (Propanamide) (Hexanamide)
l'

CH3 ~
CH3 -p-C-NH2
o
CH3 <O>-~-NH2
2,2-dimethylpropionamide Benzamide
(2,2-dimethyl propanamide)

When nitrogen is substituted, this is indicated by prefixing the name of a

rmple amide by N-, followed by the name of the substituent group. This method is
sed for both systems of nomenclature.

9 o
II "CH3
CH CH - CNHCH
3 2 3 H-C-N'CH
3
N-methyl propionamide N,N-dimethyl formamide
(N-methyl propanamide) (N,N-dimethyl methamide)
18. Amines
Common Names. The common names of amines are derived by using the suffix
-amine, preceded by the name or names of the alkyl groups attached to the nitrogen
atom, in alphabetical order. The prefixes di- or tri- are used for identical alkyl
groups. The name is written as one word. .
 N
116 OHGAKIC CHEMISTRY
CH3CH2, ,CIT.,CH2CH3
/NH CH~CH CH - N/ -
CH~CHi .' 2' 2 CH CH CH
2 2 3
Diethylamine Tri-n-Propylauune
A
CH3CH2 - NHCH3
It
EthyJmethylamine

O N,
/CH2CH3
CH3
Cyclohexylethylmethylamine 4,4' -Dimethyldiphenylarnmc
IUPAC System. In the IUPAC system, the ending·£: of the name of' the paren:
hydrocarbon contaimng the -NH:! group. is replaced by -uminc. For secondary anc
tertiary amines, the longest chain is selected as the parent alkane: in case of equa,
chain -Iengths the parent alkane is the one with the greater number of substituents
The remaining alkyl groups are named as substit uents by using the prefix N- t
indicate that they are attached to nitrogen.
CHJCH2NH2 CH./~H:!CH:~NH~ (CH3CH2)2NH
Ethanamine Propanamine N - Ethy lethanamine
(CH~CH:!. i.10Z CH
N.N - Diethyh-thanumino I .... NH'J
I ..
f:H:1 - (:[-1 ClL - ('HCH~CH:{
f5-[\[t>thyJ ;~- hr-xanamine

CR., NH:) CH
I .1
r 1- :
CH;:l-CH -- N -CH-l'H i CH.l"H~CH~ - NH --CH~ - CH-- CH:~
I .
2 -Methyl- N - propylpropanarnine
CH:~CH:)
N - ethyl- N - isopropvl -.1 -mr-rhvleih.u.armuc

O-NH2 CH3 0-(O)-NH 2

Benzenamine 4-Mcthoxybenzenamine

In more complicated arnines, the - NH;? group is considered as a substitu

on a hydrocarbon, and its positron on the chain is indicated by the lowest poss.
number.
NH.) C1L
I - I"
CH:~- CR2 - eH -- CJ:-l~~ CH - Cl l , <'H.; - C'h - COOH
l) - Met hyl - 3 - aminoh ,;lIlt'
NH:z
z-Ammopropnnoic acid
 NCLATURE OF ORGANIC COMPOUNDd 117

H2N-(O)-COOH H2NCH2CH2CH20H

p-Aminobenzoic acid 3-Aminopropanol

umber of aromatic amines have special narucs that. have been accepted by
AC.

a 6C~3
Aniline 0- Toluidine
OCH'
m- Toluidine
¢ OCH3

oeOOH NH2
. ONH-<O)
p- Anisidine

Diphenylamine
Anthranilic acid
me of the aromatic amines .irc named as derivatives of aniline.
C\\.' ('H CH

(jN0
'N/- 2 3 NH

o B'OBT 2

-Ethyl-N-methylaniline o-Nitroaniline
8r
2,4,6- Tribromoaruline

Nomenclature of Polyfunctional Compound

The functional group present in a compound determines its class. When a
mpound contains two or more different types of functional groups (polyfunctional
rnpound), the functional group which specifies its class is the pr-incipal
ctional group. The other functional groups are considered as substituents. For
xample, the compounds HOCH2CH~COCH:1 must be named 4-hydroxy-2-
tanone, not 4-butanol-2-one. The name 3-oxo-l- butanol is not preferred because
e C=O group is the principal functional group as It ranks higher in the priority
able.
lection of the Principal Functional Group
The IUPAC system has established the priority of functional groups for
etermining the class of a polyfunctional compound. Table 3.2 gives a li.st of
ctional groups in decreasing order of priority for citation as the principal
unctional group. That is, the functional group which occurs higher up in the oriority
able is the principal functional group and specifies the class. Therefore, by having a
ook at the priority table, one can at once know the class of a polyfunctional

f/"rl

~~:
 118 ORGANIC CHEMiSTRY

Table 3.2 Nomenclature Priority for Determining the Principal Functional

Group. Hi.ghe.rPriority Group is at the Top
Class Functional grOUp Suffix used
o
Carboxylic acid II -oic acid
-C-OH
, Sulphonic acid •. -S03H +sulphonic acid
o
Ester II Alkyl-oate
-C-O-:-
o
Acid halide II -oyl halide
-C-x
o
Amide II +amide
-C-NH2
Nitrile -CN -nitrile
o
Ald.ehyde II -al
-C-H
o
Ketone II -one
-C-
Alcohol -OH -01
Amine I Amine
-N-
Ethers -0- (ether)
Alkene I I -ene
-C=C-
Alkyne -€=C- -yne

'I'able 3.3 Prefixes used for Functional Groups

o
'-B!" .Bromo -R Alkyl I! Oxo
-C-
-Cl .chloro ~OR Alkoxy -N02 Nitro
-F Fluoro -OH Hydroxy -NO Nitroso
-I Iodo -NH2 Amino -cx Cyano
lUPAC Rules for Naming
----------------.------------~-----
Polyfunetional Compounds
1. Identity the principal functional group and this gives the class name of
structure. 0" 0

2. Number the longest chain containing the principal functional group from.
end nearer to it:
3, Write the parent name corresponding to the number of carbons in the long
chain,
4. Arrange the substituent r;~,meswith position numbers in alphabetical orde
:-,;,
 . t.: ~,~
NCLATURE OF ORGANIC COMPOUNDS .JI9

Prefix substituent names with the parent name.

The following functional groups are always named as substituents.
-CI Chloro -R Alkyl' -N02 Nitro
-Br Bromo -OR Alkoxy -NO Nitroso
-I lodo -NH2 Amino
-F Fluoro -CN -Cyano
C-C double or triple bonds are usually indicated by integrating -en- or -yne-
into the suffix.
Compounds containing a double bond (C=C) and a triple bond (C=C) in the
main chain are named as alkenynes. Their position number of the double
bond is inserted before -alken- and that of triple bond before -yne.

Br CI N02
I I I
CH3 -CH-:CH-CH2 -CH-CH3

o 0' 0
II II II
CH3-C =C-CH2- C-H CH3-CH2-C-CH2-C-H
5 432 1 5 4 32 1
, 3:.pentynal 3-oxopentanal
B~tli c=o and --CRO form part of the longest chain. The-CRO group is the
principal functional group as it ranks higher in the priority +,able. The ketonic
carbonyl group, C=O, is indicated by the prefix oxo.

o o
II Ir
CH3- C-CH2-CH20H CH3 CH = ca- C- CH2 -CH3
1 2 3 4 6 5 4 3 2 1
4-Hydroxy-2-butanone 4-Hexen -3-one

OH OCB3
I I
CH2 :-::CH-CH2 -CH-CH3 , CH3 - CH2 - CH - CH20H
54321 4 3 2 1
4-Penten -2-01 2-Methcxy -1-butanol

In both the above compounds, the -OR group is the principal functional groups. Th·
.:!qc1I3 is always treated as a substituent and is indicated by the prefix methoxy

"
120 ORGANIC CHEMISTRY

oII CH.,
I .)
CH3 NH2
I I
CH:~--C - CH2 - CH - COOH CH3- CH - CH2- CH - CH2-COOH
54:3 21 6 s 1 3 2 1
2-Methyl-4-oxopentanolC ac.d ;j-Amino-5-methylhexanoic acid

In both the above compounds, the -COOH groups is the funcational group as it
ranks highest in the Priority table. The ketonic carbonyl group (C=O) is indicated by
the prefix oxo. The -NH::?group is indicated by the prefix amino. •
OIl 0 OCH~ O·
I II I - 1\
CH3 - CH - CH2 - C -- OCH2CH3 CH3 - CH? - CH - CH2 - C - Cl
432 1 54- 3 2 1
Ethyl 3-hydroxyb1.!tmoate 3-Methoxypentanoyl chloride
o
II
The - C -0 group is the principal functional group and the compound is named as
o
II
ester. The - C - CI is the principal functional group and the compound is named as
an acid halide.
I
CN 0 0
I 1\ II
CH3 - CH - CH = CH - C - CH2 - C - H
765432 1
6-cyano- 3-oxo-4-heptenal
,
The functional groups are -CN, C=C, -CO-, and -CHO. The -CHO group is the
principal functional group and the compound is named as aldehyde.

oII OH
I
(CH3)2C = CHCH2CH2 - C - CH3 (CH3hC = CHCH2CH2 - CH - CH3
6 5 4 3 2 1
6-Methyl- 5-hepten- 2-one 6-Methyl-5-hepten-2-o1

oII 0
II
oII 0
II
CH3 - C - CH2 - C - CH3 CH3CH2 - C - CH2CH2 - C - OCH3
2.4- Pentanedione Methyl-s-oxohexanoate

OCH 3 OH

o-Hyc "uxybenzoic acid OCH3

¢ CH2CH=CH2
tSalicylic acid)
p-Methoxyethylbenzcne p-allylphenol
 ,fENCLATURE OF ORGANIC COMPOUNDS 121
COOH

5:HO
ormylbenzoic acid
¢ S03H
.. o S03H
p-sulphobenzoic acid p- Toluenesulphonic acid
4 Heterocyclic Compounds
Thos cyclic compounds which, in addition to carbon, have at least one atom of
other element (heteroatom) in the ring are called heterocyclic compounds or
nnply heterocycles.

ommon Names Heterocyclic compounds are usually called by their

mmon names. Their numbering starts from the hetero atom and proceeds
round the ring so as to give the substituents the lowest number.
IUPAC System. The system combines prefixes, which indicate the nature of
he hetero atom present, with stems, which indicate the size of the ring. The
prefixes are the same as those listed in table. 3.4. for use in substitution
names, except the terminal a is usually elided since the stems, which are
isted in table' 3.5~illl begin with vowels. When there is more than one kind
of ring hetero atom, the atom of higher atomic number receives the lower
number in naming the compound.
Table.3.4 Characteristic Prefixes for Replacement Names
Element Prefix
Oxygen oxa-
Nitrogen aza-
Sulphur Thia
Phosphorus Phospha
Silicon Sila'
Table. 3.5. Stem for use in Nomenclature of Heterocyclic Compounds
I I Stem I

Ring size
Saturated Unsaturated
:; Irane irine
4 etane ete
5 olane ole
6 ixane ixine
7 epane epine
8 ocane ocme
(i) In numbering rings, a single hetero atom is given number 1. The
substituents are then numbered in lthe usual., manner.
I
122 ORGANIC CHEMISTRY
(ii) When a hetero atom occurs more than once, the hetero atoms are given
the lowest posgible numbers. .
(iii) If isomers are possible as a result of the positions of one or more
hydrogens, the position of each hydrogen is indicated by means of the
prefix 1H, 2H, 3H etc.
The IUPAC names are given in parentheses.

oFuran
o S
Thiophene
o· N
I
o· o
tetrahydrofuran
H
(oxole) (Thiole) Pyrrole (oxolane)
(azole)

o N
H
I
Pyrrolidine
H2C-CH2
"0/
Ethylene oxide
cr [J N
imidazole
(l,3-diazole)
. S
(l,3-thiazole)
(oxirane)
(azolidine)

D0""'"
(1 ,2-oxaz~le)
IN
o
. N
Pyridine
(azine)
o oH
I
dioxane
Piperidine (1 ,4-dioxane)
(perhydroazine)

() O
N
Pyrazine
(1,4-diazixine)
N~
Pyrimidine
(1,3-diazixine)
~N
o CO
o
Pyran
(4H-oxirine)
~
N
quinoline
(l-azanaphthalene)
~
I~

8 9 I 4
7'7 ~ ~2

0vN
~ 5~3

isoquinoline
6~
5
~
N
10
~3
4
6U~T)2
7 ~
(2-azanaphthalene) acridine H
(10-azanthracene) indole
(l-azindene)

Ol-CH
S 3
()3
N U·
H3C '0 CH3
2-methylthiophene 3-methyl pyridine
2,5-dimethylfuran
(2-methylthiole) (3-methyl-azixine)
(2,5-dimethyloxole)
 TURE OF ORGANIC COMPOUNDS 123

V-CHO
Furfural
_-formyloxole)
OR N
HC-C=O
2 I I
H2C, /0
C
H2
Isonicotinic acid y-Butyrolactone
(azixine-s-carboxylic acid) (oxalane-2-one)

'~9
'c/-C-C6Hs
' rl
ZAPo
S03H

N
(3H-1,2,4-triazole)
1-:L
oylthiophene 3-furansulphonic acid
_,-oenzoylthiole)
eterocyclic compounds containing more than one ring are
~-~ontly named by combining the names of the indicated rings, e.g.,

00 o
benzoftuan
00 N
~
benzopyrrole

II .Questions II
Name the following alkyl groups: (a) CH3 - (b)CH3CH2 - (c) CH3CH2CH2-
d (CH3)2CH- (e) (CH3)3C-
Tritethe structural formulas for the following compounds:
a) 2-Buten-l-ol ~. (b) 6-Methyl-5-hepten-2-o1
c) 2-Pentanone :;, .' ',\0. (d) 1,3-Butadiene
e) 3-Hydroxypropanoic acid (f) 4-penten-2-one
g) 6-cyano-3-oxo-4-heptenal (h) 4-oxopentanoic acid
rite structural formulas for the following compounds.
a) p-Nitroaniline (b) Mesitylene (c) Durene
d) Biphenyl (e) Cumene (f) Anthrancene
g) Triphenylmethanol (h) 3-oxopentanal
i) 4-Acetylbenzoic acid (j) Benzoic anhydride
Write the IUPAC names ofthe following compounds.
oII II
0
I a) H - C- CH2 - CH2 - CH2 - C-OH (b) HO - CH2 - CH2 - COOH
o
II
(c) CH2 = CH - C == C:H (d) CH3 - C- OCH2CH3