Nomenclature of Organic Compounds

Content
• Nomenclature of organic compound belonging to the following
classes Alkanes, Alkenes, Dienes, Alkynes, Alcohols, Aldehydes,
Ketones, Amides, Amines, Phenols, Alkyl Halides, Carboxylic Acid,
Esters, Acid Chlorides And Cycloalkanes.
Nomenclature
Why is nomenclature necessary?
Organic chemistry is a vast branch as millions of organic
compounds are already known and thousands of new compounds
are being added to this list every year. In order to facilitate the
study of such large number of compounds. Therefore it is
necessary to classify the organic compounds. In order to classify
this organic compounds the term "Nomenclature" comes into
picture.
Nomenclature
What is nomenclature?
Nomenclature means the assignment of names to the organic
compounds. The naming of organic compounds is an important
aspect in the study of organic chemistry as their number is very
large and variety of molecular structures exist in their molecules.
The field has become more complex on the phenomenon of the
isomerism. They are two main systems of nomenclature of organic
compounds.
They are
1.Trvial system
2.IUPAC system
Nomenclature
Trivial System
In this system whenever a new compound is discovered it is given
an individual name. These names are called Trivial names. These
names are also called Common names.
Examples
(a) Acetic acid derives its name from vinegar of which it is chief
constituent.
(b) Formic acid was named as it was obtained from red ants.
(c)The name oxalic acid, malic acid and citric acid is derived from
botanical sources.
IUPAC Nomenclature
• IUPAC stands for International Union of Pure And Applied Chemistry.
They have given certain rules to systematize the nomenclature of
organic compounds. The names based upon
• these rules are called IUPAC names.

• The IUPAC name of any organic compound can be derived by using

the rules as described in the following slides. IUPAC

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IUPAC Nomenclature
Features of IUPAC system
(a) A given compound can be assigned only one name
(b) This system is helpful in naming the complex organic
compounds
(c) This system is helpful in naming the multifunctional groups.
(d) This is a simple, systematic and scientific method for the
nomenclature of organic compounds.
IUPAC Nomenclature
Rules for organic nomenclature:
For naming the organic compounds systematically first we have to
first study about the following Four features
(a) Root word
(b)Primary suffix
(c)Secondary suffix
(d)Prefix
a) Root Word
The basic unit in organic nomenclature is the root word. Chains containing one
to four carbon atoms are known by special root words while chains from C5
onwards are known by greek number roots.
Chain Root Chain Root
length word length word

C1 Meth- C6 Hex-
C2 Eth- C7 Hept-
C3 Prop- C8 Oct-
C4 But- C9 Non-
C5 Pent- C10 Dec-
b) Primary Suffix
The primary suffixes are added to the root word to show saturation or
unsaturation in a carbon chain.
Name of Carbon Chain Name of Primary Suffix IUPAC Name
Saturated -ane Alkane
Unsaturated With one
double bond -ene Alkene

Unsaturated with one -yne Alkyne

triple bond
Unsaturated with two
double bonds -adiene Alkadiene

Unsaturated with three

double bonds -atriene Alkatriene
c) Secondary Suffix
Suffixes that are added after the primary suffixes to indicate the presence of a
particular functional group in carbon chain is called the secondary suffix.
Functional Secondary Functional Secondary Suffix
Group Suffix Group
Alcohol ( -OH ) -ol Thioalcohol(-SH) -thiol
Aldehyde( -CHO ) -al Cyanide (-CN) -nitrile
Ketone( -CO) -one Esters (-COOR) -oate
Carboxylic acid -oic acid Amides (-CONH2 -amide
( -COOH) )
Sulphonic acid -Sulphonic acid Acid halide (- -oyl halide
( -SO3H) COX)
Amine(-NH2) -amine Thioalcohol(-SH) -thiol
d) Prefix
It is always be kept in mind that alkyl groups forming branches of the
parent chain are considered as side chains. Atoms or groups of
atoms such as Halogen(-X), Nitro(-No2) and Alkoxy(-OR) are referred
to as substituents. Root words are prefixed with the name of the
substituent or the side chain.

Arrangement of Prefixes, Root word and Suffixes

These are arranged a follows while writing the name in such a
manner.
IUPAC name = Prefixes + Root word + Primary Suffix + Secondary
suffix
d) Prefix

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Saturated Aliphatic compounds Nomenclature
Longest Chain Rule : This rule states that in naming an organic
compound we have to select the longest continuos chain of carbon
atoms which may or may not be horizontal. This continuos chain is
called the "Parent Chain" or "Main Chain".

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Saturated Aliphatic compounds Nomenclature
Lowest Sum Rule: the numbering of carbon atoms should be done in such a way
that the sum of the positions of the substituent atoms attached should be
minimum.
In correct numbering the methyl groups are at 2nd and 3rd positions. Sum of
positions is 2+3=5.

In wrong numbering the methyl groups are at 3rd and 4th positions. Sum of
positions is 3+4=7.

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Alkanes
General formula:- CnH2n+2
Suffix:- ane
1) These are the organic compounds which contain only carbon-carbon single
bonds.
2)According to IUPAC system, these are named as alkanes.

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Alkenes
General formula : 𝐶𝑛𝐻2𝑛.
• Functional group : 𝐶 = 𝐶(double bond)
• Suffix : ene
• Names. Replace the terminal ‘ane’ from the name of the corresponding alkane
by suffix ‘ene’.

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Alkynes
General formula : 𝐶𝑛𝐻2𝑛−2.
• Functional group : 𝐶 ≡ 𝐶 (triple bond)
• Suffix : yne
• Names. Replace the terminal ‘ane’ from the name of the corresponding alkane
by suffix ‘yne’.

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Dienes
• General formula : CnH2n–2.
• Functional group : 𝐶 = 𝐶(double bond)
• Suffix : diene
• Name the longest chain that contains both double bonds.
• The chain is numbered in such a way that the double bonds end
up with the lowest possible numbers, exception made when there
is another dominant function in which case the numbering starts
by it.
Dienes

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Alcohols
General formula : 𝐶𝑛𝐻2𝑛+1𝑂𝐻.
• Functional group : 𝑂𝐻 (hydoxyl)
• Suffix : ol
• Names. Replace the terminal ‘e’ from the name of the corresponding alkane by
suffix ‘ol’.
these are called alkanols and their names have been derived by changing -e of
corresponding alkane by –ol

Image source : Organic Chemistry by Maheta and Maheta, 2 nd edition

Aldehydes
General formula : CnH2n+1CHO.
• Functional group : -CHO (aldehyde)
• Suffix : -al
• Names. Replace the terminal ‘e’ from the name of the corresponding alkane by
suffix ‘ol’.
These are called alkanals in the IUPAC system of nomenclature and the names of
individual members are derived by changing –e of corresponding alkane by –al.

Image source : Organic Chemistry by Maheta and Maheta, 2 nd edition

Ketones
General formula : CnH2n+1COCmH2m+1.
Functional group : >C=O (Keto)
Suffix : -one
Thus the functional group called ketonic group contains a carbon atom joined to
the oxygen atom by double bond.
The names of individual members are derived by replacing –e of the
corresponding alkane by –one.

Image source : Organic Chemistry by Maheta and Maheta, 2 nd edition

Amides
General formula : RC(=O)NR′R″, where R can be Organic Group or Hydrogen.
• Functional group : -CONH- (Amide)
• Suffix : Amide
• Primary amides are named by changing the name of the acid by dropping the
-oic acid or -ic acid endings and adding -amide. The carbonyl carbon is given the
#1 location number. It is not necessary to include the location number as
functional group will be on the end of the parent chain.

O O
O O O Cl
NH2 NH2
H NH2 H3C NH2 NH2
formamide acetamide Br
or benzamide 3-chlorobenzamide
or 2-bromobutanamide
Methanamide Ethanamide
 Amides
• Secondary amides are named by using an upper case N to designate that the
alkyl group is on the nitrogen atom. Alkyl groups attached to the nitrogen are
named as substituents. The letter N is used to indicate they are attached to the
nitrogen.
O
NH
NH NH NH
O
O O
N-methylpropionamide N-ethylbutyramide N-methylbenzamide N-phenylacetamide

• Tertiary amides are named in the same way as secondary amides, but with two
N's
O O

H N N

N,N-dimethylformamide N,N-dimethylpropionamide
Amines
General formula : CnH2n+1-NH2.
• Functional group : -NH2
• Suffix : -amine
• These are the alkyl derivatives of ammonia. They are formed by replacing one,
two or all the three hydrogen atoms in ammonia with alkyl radicals. In IUPAC, the
name is derived by replacing –e of alkane by amine.

Image source : Organic Chemistry by Maheta and Maheta, 2 nd edition

Phenols
• Derived from aromatic hydrocarbon.
• The class of organic compounds where hydoxy group (–OH) is directly attached
to benzene ring is termed as phenols.
• One or more –OH group is attached to aryl ring.

Image source : Organic Chemistry by Maheta and Maheta, 2 nd edition

Alkyl Halides
General formula : CnH2n+1X or RX.
• Prefix : Halo
• These are obtained from alkanes by the replacement of one or more hydrogen
atoms by halogen atoms.
• In the IUPAC system, they are named as halogen substituted alkanes i.e.,
haloalkanes. Thus the name of halogen compound is given by prefixing flouro,
Chloro, bromo, iodo to the names of the alkane.

Image source : Organic Chemistry by Maheta and Maheta, 2 nd edition

Carboxyllic acid
General formula : CnH2n+1COOH.
Functional group : -CO𝑂𝐻 (Carboxyl Acid)
Suffix : -oic acid
In this compounds, one hydrogen atom in alkane molecule is replaced by a
carboxyl (COOH) group. The first member is, however, obtained by replacing a
hydrogen atom in the hydrogen molecule.
• In the IUPAC system, they are named by replacing the terminal –e of the
corresponding alkane by –oic acid.

Image source : Organic Chemistry by Maheta and Maheta, 2 nd edition

Esters
General formula : 𝐶𝑛𝐻2𝑛+1COO𝐶m𝐻2m+1.
• Functional group : -COO- (Carboxylate)
• Suffix : -oate
• Are named by changing the name of the acid by dropping the -oic acid or -ic acid
endings and adding –oate, Preceded by R group of ROH.

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 Acid Chlorides
General formula : CnH2n+1COCl.
• Functional group : -COCl-
• Suffix : –oyl chloride or –yl chloride
• Are named by changing the name of the acid by dropping the -oic
acid or -ic acid endings and adding –oyl chloride or –yl chloride.

O O
O
O
Cl Cl
Cl
Cl
acetyl chloride 2-methylbutanoyl chloride benzoyl chloride
4-ethylbenzoyl chloride
Cycloalkanes
General formula : CnH2n.
• Prefix : -ali or –Cyclo.
Done by following rules:
1. Unsubsituted alkane is named by attaching prefix cyclo- to the name of the
corresponding normal alkane having same number of carbon atoms as in the
ring.
H2
H2 C
C
H2C H2C CH2 H2C H2C CH2
CH2 CH2
H2C H2C CH2 H2C H2C CH2
C C
cyclopropane cyclobutane H2 H2
cyclopentane cyclohexane
Cycloalkanes
2. Subsituents on the ring-alkyl group or halogens- are named, their position are
numbered in such a manner that carbon bearing substituents get the lowest
combination of numbers. CH3

Br
CH
H2C HC H2C CH2

H2C CH2 H2C CH

bromocyclobutane C CH3
H2

1,3-dimethylcyclohexane

3. Cycloalkenes and Cycloalkynes the doubly and triply bonded carbons are
considered to occupy position 1 and 2. For Example
H3C
H
C
CH2
HC CH2
HC
HC H2C CH
CH2 C
HC H

3-ethylcyclobut-1-ene cyclohexa-1,4-diene
 Cycloalkanes
4. If a functional group containing carbon is directly attached to alicyclic
ring, the carbon atom of this group is suitably included in the suffix used for
the group. For e.g., O
O

OH

cyclopentanecarbaldehyde cyclobutanecarboxylic acid

5. Alcohols are given the name ending –ol, which takes priority over –ene
and appears last in name. For e.g.,
OH

cyclohex-3-enol
IUPAC Nomenclature
RULES FOR NAMING COMPOUNDS HAVING MORE THAN ONE FUNCTIONAL
GROUP & /OR SUBSTITUENT &/OR MULTIPLE BOND:
• when more than one functional groups are present, one functional group is
chosen as the PRINCIPAL FUNCTIONAL GROUP—written as a suffix, while
others are regarded as substituents—written as a prefixes.
• To remove any confusion, the functional groups are arranged in a
preference series as follows:
Carboxylic acid>Sulphonic acid>Anhydride>Ester>Acid
chloride>Acid amide>Nitrile>Aldehyde>Ketone>Alcohol>
Amines>Alkene>Alkyne
• The group higher in the preference series is written as a Suffix While the one
lower to it would be written as a Prefix.
IUPAC Nomenclature

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