O

Organic chemistry
i   h i
Nomenclature of 
Organic compounds

Bridge course
 Nomenclature of organic
compounds
Th are two
There t systems
t off naming
i
1 Trivial system
1.
2. IUPAC system
y
Trivial system:

When a few organic

g compounds
p were known,,
they were named on the basis of their history
or source.
source
Eg: HCOOH –Formic acid (red ants)
CH3COOH‐Aceticacid
COOH A ti id (acetum‐vinegar)
( t i )
IUPAC system:
(International Union of Pure and 
Applied Chemistry)

By using this system one can name any 
B   i  thi   t          
complex organic compound easily.
The name assigned to an organic 
compound on the basis of latest IUPAC 
p
rules is known as systematic name.
W iti IUPAC name off a compound
Writing d
y The IUPAC name of the compound
p
built from 4 parts
y Prefix
y word root
y primary suffix
y secondary suffix
Prefix
y It denotes the substituent group if  
present in the organic compound
p g p
Substituent group prefix
‐F Fluoro
l
‐Cl
Cl chloro
‐Br Bromo
substituent prefix
‐I                                            Iodo
‐NO2                                     Nitro
NO2                                     Nitro
‐CH3                                      Methyl
‐C2H5                                    Ethyl
‐C3H7                                    Propyl 
3 7 py
Word root
y It indicates the number of carbon atoms in
the longest possible chain.

N off carbon
No. b atoms word
d root
1 meth‐
2 eth‐
3 prop‐
No.of carbon atoms Word root
4 but‐
5 pent‐
6 hex‐
7 hept‐
p
8 0ct‐
9 non‐
10 dec‐
Primary Suffix
yIt denote the nature of carbon to
carbon bond in the organic
compounds.
yane: b d
bond
yene: bond
yyne: bond
S
Secondary
d suffix
ffi
It represents the functional group if
present in an organic molecule and is
attached
h d to the
h primary
i suffix
ffi while
hil
writing the IUPAC name.
Class of                      functional       secondaryy
compounds                 group              suffix

Alcohol                           ‐OH                       ‐ol
Aldehydes                      ‐CHO                     ‐al
Ketones                          >C=O                     ‐one
Carboxylic acids           COOH                     oic acid
Carboxylic acids          ‐COOH                    ‐oic acid
Amines                          ‐NH2                       ‐amine
E t                              COOR                     t
Esters                            ‐COOR                    ‐0ate
Writing
W ii IUPAC name off an
aliphatic compound

IUPAC=   prefix (es)+word root + primary   
IUPAC     fi  ( ) d  t    i    
suffix +secondary suffix
Eg:
g H2
H3C CH C OH
3 2 1
Word root
root-:: prop CH3

Prefix -: methyl
Pi
Primary suffix-:
ffi -ane
Secondary suffix-: -ol
IUPAC name- 2-Methyl-1-propanol

(terminal ‘e’ of the p-suffix is dropped if the sec-suffix begins

with
ith a,e,i,o,u)
i )
IUPAC rules for naming organic
compounds
1.Longest chain rule:
Select the longest continuous chain of carbon atoms
known as “parent” chain
1 2 3 4 5 3 4 5 6
CH3-CH-CH2-CH2-CH3 CH3-CH-CH2-CH2-CH3
| |
CH2-CH
CH3 CH2-CH
CH3
2 1
2-Ethylpentane
2 Ethylpentane 33-Methyl
Methyl hexane
(wrong) (correct)
2.Lowest number rule
The carbon chain selected is numbered from the end
nearest to the side chain or substituent so as to give the
lowest number to the carbon carrying the side chain.
1 2 3 4 4 3 2 1
CH3-CH-CH2-CH3 CH3-CH-CH2-CH3
| |
CH3
C CH3
C
2‐Methylbutane 3‐Methylbutane
( correct)) (
(wrong)
)
Lowest sum rule:
Where there are more than one substituent, numbering
of the chain is done in such a way that the sum of the
numbers assigned to the substituents is minimum.
“Thee teterm Locant
oca t iss used to de denote
ote tthe
e number
u be
indicating the substituent attached”.
CH3 CH3 CH3 CH3
1 2| 3 4| 5 5 4| 3 2| 1
CH3-C-CH2-CH-CH3 CH3-CH-CH2-CH-CH3
| |
CH3 CH3
2,2,4‐trimethylpentane
2,2,4 trimethylpentane 2,4,4‐trimethylpentane
2,4,4 trimethylpentane
Set of locants= 2+2+4=8 set of locants=2+4+4=10
(correct) (wrong)
3  Arrangement of Prefixes
3. Arrangement of Prefixes
If more than one group is attached to the carbon 
chain, these groups should be arranged alphabetically. 
When two or more identical substituents are present 
prefixes like di, tri, tetra, etc. are used. However these 
prefixes are not considered for alphabetical order.
1              2          3             4          5            6                                     1              2        3 4         5              6
CH3-CH-CH2-CH-CH2-CH3
CH3 CH CH2 CH CH2 CH3 CH3-CH-CH2-CH-CH2-CH3
CH3 CH CH2 CH CH2 CH3
| | | |
CH3          CH2                                      CH3       CH2
| |
CH3 CH3

2-Methyl-4-ethylhexane 4-Ethyl-2-methylhexane
(wrong)                                                   (right)
y If two different groups are located at the equivalent
positions, the
h numbering
b should
h ld beb done
d in such
h a
way that alkyl group which comes first in the
alphabetical
p order g
gets the lowest p
position.
1 2 3 4 5 6

CH3-CH
C C 2-CH-CH-CH
C C C 2-CH
C 3
| |
C2H5 CH3

3-Ethyl-4-methylhexane
 4: Lowest Number to the Functional
Groupp
y In case there is a functional group in a molecule, 
the parent chain is numbered such that the 
f
functional group gets the lowest number, even if 
ti l    t  th  l t  b    if 
the lowest number rule is violeted. 
CH3 CH3
H2 H
H3C C CH3
H2 H
C C
1 2 3 4 5 H3C C C C CH3
5 4 3 2 1
CH3 OH
CH3 OH
2,2-Dimethylpentan-4-ol
2,2 Dimethylpentan 4 ol 4,4-Dimethylpentan-2-ol
, e y pe o
wrong Right
5 Presence of Identical groups
If an organic molecule has more than one functional 
group, prefixes like di, tri, tetra are used before the 
  fi  lik  di   i       d b f   h  
suffix indicating the functional group. However, the 
‘e’ of the corresponding alkane is retained
e  of the corresponding alkane is retained.
4 3 2H 1 2 1
H3C CH C CH2 H2C CN

OH OH OH H2C CN
3 4
Butane-1,2,3-triol Butane-1,4-dinitrile
Nomenclature of unsaturated hydro carbons

H2
a ) H 3C C C CH2 b) H3C C C CH3
H2 1 2 3 4
4 3 1
But-1-ene But-2-yne

5 4 3 2 1
c) H3C C C C CH2
H H H

Penta-1,3-diene
 IUPAC nomenclature of poly
functional compound

In case of polyfunctional
compounds one of the functional
group chosen as the principal
group andd the
th compound
d is
i namedd
on that basis.
The order of decreasing priority
for functional groups
g p
Sulphonicacid>carboxylic acid>ester>acid chloride
>amide> nitrile> aldehyde>
y ketone>
alcohol>amine>doublebond>triple
bond>ether>other substituents (X>NO2>R)
H2 H2 H2
OHC C C C COOH
4 3 2 1
substituent group principal functional group
4-Formylbutanoicacid
 The IUPAC name of an alicyclic compounds
is prefixed with “cyclo”.
NO2

3 1
2 2
a)) b) c)
3
1
Cyclohexane
y 3-Nitrocyclohexene
y
1-Methyl-3-propylcyclohexane
 Nomenclature of Aromatic
compounds
NH2
6 Cl
1 CH3
5 1
a) b) 6 2

O2N
4 2 NO2 5 3
3
4

C2H5

1-Chloro-2,4-dinitrobenzene 4-Ethyl-2-methylaniline
IUPAC names of organic compounds 
by bond line notation
b  b d li   i
a b

But-2-ene
2,3-Dimethylbuta-1,3-diene

d
c

2,2-Dimethylbutane 3,3-Diethylpentane
THANK YOU

BRIDGE COURSE‐2012