Nomenclature

of

organic

compounds
Bibek Raj Bhattarai

©Bibek Raj Bhattarai

 There are two different systems, which are
generally used for writing the names of organic
compounds.

1. Common system or trivial system

Nomenclature
of organic
compounds
2. IUPAC system

©Bibek Raj Bhattarai

 Common system is an old system of nomenclature of
compounds which doesn’t involve any systematic
pattern or scientific rules rather they were named
according to their source of origin.

• For examples, CH4 is named as marsh gas as it

1. Common evolves from marshy land (Latin, marsh= damp).

system or • HCOOH was named as formic acid because it was

trivial system obtained from red ant (Latin, formica=ant)

• C6H12O6 is named as glucose (glucosa=sweet).

• NH2CONH2 as urea (urea=urine).

©Bibek Raj Bhattarai

 • There is no exact rule of naming the compound and
no exact relation between the structure and name
of the compound i.e., unsystematic.

• However, this system can’t be avoided because of

its simplicity, popularity and familiarity to the
1. Common people.

system or • For example, glycerin is more familiar among

trivial system common people then its IUPAC name propane-
1,2,3-triol.

• On the other hand, IUPAC name of some

compounds are too vague to write and speak as
compared to the common names.

©Bibek Raj Bhattarai

 • In 1957, the International Union Of Pure and
Applied Chemistry (IUPAC), evolved a
scheme for giving system names to organic
compounds on the basis of structure.

• This system has set rules for naming organic

2. IUPAC compounds taking no. of carbon atoms present

in it and structure under consideration.
System
• It is latest scientific system of nomenclature
and accepted worldwide.

• This system makes the study of organic

compound easier as it gives an insight into the
structure of molecules.

©Bibek Raj Bhattarai

 • One compound can have only one IUPAC
name through the world and thus it removes
the confusion in the name of organic
compounds that happens in common system.

• Naming organic compounds is an essential

2. IUPAC skill which enables us to write correct name of
System a compound or correct name from the
structures.

• An organic compound is named by combining

different terms.

• For example;
©Bibek Raj Bhattarai
Some Terminology
Word Root: It represents the number of carbon atom in the parent chain.

Carbon chain Word root Carbon chain Word root

C1 Meth C9 Non
C2 Eth C10 Dec
C3 Prop C11 Undec
C4 But C12 Dodec
C5 Pent C13 tridec
C6 Hex C14 tetradec
C7 Hept ……….. ………..
C8 Oct C20 eicos
©Bibek Raj Bhattarai
 Some Terminology
Prefix: It is written before word root. It is of two types:
a) Primary Prefix:
It is used to indicate the cyclic or acyclic nature of the given compound.
For example;

Nature of compound Prefix used

cyclic compounds cyclo
Fused and bridged bicyclic bicyclo
Cyclobutane Cyclopentane Cyclohexane
spirocyclic compounds spiro

©Bibek Raj Bhattarai

 Some Terminology
b) Secondary Prefix:
It is used to indicate the side chains, substituents and low priority functional groups (which are
considered as substituents)
Side chain or Substituents Prefix
R- Alkyl-
CH3- Methyl-
CH3-CH2- or (C2H5) Ethyl-
X- (F-, Cl-, Br-, I-) Halo-(Fluoro-, Chloro-, Bromo-, Iodo-)
-NO2 Nitro-
NO- Nitroso-
-OH Hydroxy-
-OR Alkoxy-
CN- Cyano-
Note: If two or more different prefixes are present, we put them according to alphabetical order.
©Bibek Raj Bhattarai
 Some Terminology
Suffix: It is further divided into two types:
a) Primary Suffix:
It is used to indicate the degree of saturation or unsaturation in the main chain. It is added
immediately after the word root of IUPAC name. (nature of bonding)

Types of carbon chain Primary suffix

Saturated (all C-C bonds) -ane
Unsaturated: one C=C -ene
Unsaturated: two C=C -diene
Unsaturated: one C≡C -yne
Unsaturated: two C≡C -diyne

Unsaturated: one C=C & one C≡C -enyne

©Bibek Raj Bhattarai

 Some Terminology
b) Secondary Suffix: It represents main functional group (FG) which is written after primary suffix.
Name of FG Representation Suffix
Carboxylic acid -COOH -oic acid
Sulphonic acid -SO3H -sulphonic acid
Acid anhydride -O-CO-CO-O- -oic anhydride
Ester -COOR -alkyl -oate
Acid halide -COX -oyl halide
Acid amide -CONH2 -amide
Cyanide/Nitrile -CN -nitrile
Aldehyde -CHO -al
Ketone -CO- -one
Alcohol -OH -ol
Thiol -SH -thiol
Amine -NH2 -amine
©Bibek Raj Bhattarai
 Some Terminology
Formulation of IUPAC Name (Format of writing IUPAC name)

2o prefix + 1o prefix + word root + 1o suffix + 2o suffix

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s begin with naming the alkane:
Rule 1: Longest chain rule
The longest carbon chain in the molecule is identified. For example:

Selection of parent chain as shown in

(II) is not correct because it has only
eight carbons. So, selection of chain (I)
is correct.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s find the longest chain in the following molecules.
a b c

f
d e

g
h i

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Rule 2: Lowest number rule or lowest set of locants rule
The numbering is done in such a way that the branched carbon atoms get the lowest possible numbers.
For example:

Thus, the numbering in the given example should be from left to right (branching at carbon
atoms 2 and 6) and not from right to left (giving numbers 4 and 8 to the carbon atoms at
which branches are attached). ©Bibek Raj Bhattarai
 Rules for IUPAC Nomenclature
Let’s provide the acceptable numbering in the following molecules.
a b c

f
d e

g i
h

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Rule 3: If two or more identical substituent groups are present then the numbers are separated by
commas. The names of identical substituents are not repeated, instead prefixes such as di (for
2), tri (for 3), tetra (for 4), penta (for 5), hexa (for 6) etc. are used. While writing the
name of the substituents in alphabetical order, these prefixes, however, are not considered.

2,4-dimethylpentane 2,2,4-trimethylpentane 3-ethyl-4,4-dimethylheptane

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Rule 4: If the two substituents are found in equivalent positions, the lower number is given to the one
coming first in the alphabetical listing.

Name of compound as per the indicated numbering

3-ethyl-6-methyloctane
(Correct because ethyl comes first than methyl in
alphabetical listing)

Name of compound as per the indicated numbering

6-ethyl-3-methyloctane
(wrong)

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s try the naming of the following alkanes.
a b c

f
d e

g i
h

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s try more….
1. Draw the structure of following alkanes.
a. 3-ethyl-2-methylhexane
b. 3,3,4-trimethylheptane
2. Write the IUPAC name of
a. (C2H5)2-CH-CH3
b. (CH3)2-CH-CH2-C(CH3)2-CH3
3. Write the IUPAC name of following structure.
a. b. c. d.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s move to naming of alkene and alkyne
1. Longest chain is selected as in alkane such that the chain must contain double or triple bond (even
if it is not the longest chain).

2. The numbering should be done in such a way that the double or triplet bond get lowest number or
lowest set of locants. The position of double or triple bond is mentioned in IUPAC naming.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s move to naming of alkene and alkyne
3. If both double and triple bond (multiple bonds) are present in a molecule, the numbering is done
in such a way that the multiple bonds get lowest set of locants.
While writing the name of such multiple bond, alkene with its position is written first in
IUPAC naming than alkyne with its position is written. i.e. ene is written before yne.
If ene + yne = drop ‘e’ of ene
If ene + diyne = do not drop ‘e’ of ene

pent-3-en-1-yne oct-2-en-5-yne

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s write the IUPAC name of following alkenes and alkynes
a. b. c. d.

e. f. g. h.

i. j. k.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s write the IUPAC name of following alkenes and alkynes
a. b. c.

d.
e.

f. g.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s move to organic compounds containing one functional group
1. Longest chain is selected as in alkane. If the functional group contains carbon, the carbon is
counted as a part of the chain. If the suffix of functional group starts with vowel letter, last vowel
of primary suffix (ane, ene, yne, etc.) is dropped.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s move to organic compounds containing one functional group
2. The numbering should be done in such a way that the functional group get lowest number or
carbon containing terminal functional group (-COOH, -CHO, -CN, etc.) gets number 1.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s move to organic compounds containing one functional group
2. The numbering should be done in such a way that the functional group get lowest number or
carbon containing terminal functional group (-COOH, -CHO, -CN, etc.) gets number 1.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s move to organic compounds containing one functional group
3. If an organic compound contain functional group, double bond, triple bond, or substituents then
the order of priority will be

Functional group > double bond > triple bond > substituent

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s practice naming of compounds containing one functional group
b.
a.

c. d.

e. f.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s move to naming of compounds containing two or more functional groups
Name of FG Representation Suffix Prefix
Carboxylic acid -COOH -oic acid carboxy-
Sulphonic acid -SO3H -sulphonic acid sulpho-
Acid anhydride -O-CO-CO-O- -oic anhydride -
Ester -COOR -alkyl -oate alkoxycarbonyl-
Acid halide -COX -oyl halide halocarbonyl-
Priority of Acid amide -CONH2 -amide carboxamido
functional
Cyanide/Nitrile -CN -nitrile cyano-
group
Isocyanide/isonitrile -NC -isonitrile or carbylamine Isocyano-
Aldehyde -CHO -al formyl-
Ketone -CO- -one oxo- or keto-
Alcohol -OH -ol hydroxy-
Thiol -SH -thiol mercapto-
Amine -NH2 -amine amino-
©Bibek Raj Bhattarai
 Rules for IUPAC Nomenclature
Let’s practice naming of compounds containing two or more functional groups
a. b. c.

d. e. f.

©Bibek Raj Bhattarai

 Rules for IUPAC Nomenclature
Let’s practice naming of compounds containing two or more functional groups

g. h.

i. j.

©Bibek Raj Bhattarai

Practice Exercise
Ans:
a. but-3-en-2-ol
b. 3-hydroxybutan-2-one
c. 2- bromo 3- chloro butane
d. 6-amino 6-bromo hept-2-en-4-yn-1-al
e. 2-chloro-pent-3-en-1-ol
f. 3-hydroxyhexanoic acid
g. 4-bromo 3-chloro 3-cyanohexanal
h. 1-aminobutanol
i. 3-methyl 2-nitropentanesulphonic acid
j. 4-hydroxy 2-methylpentanal

©Bibek Raj Bhattarai

Practice Exercise

©Bibek Raj Bhattarai