IUPAC NAMING & ISOMERS (1)

IUPAC NAMING OF HYDROCARBONS
Here is a simple list of rules to follow. Some examples are given at the end of the list.
1. Identify the longest carbon chain. This chain is called the parent chain.
2. Identify all of the substituents (groups appending from the parent chain).
3. Number the carbons of the parent chain from the end that gives the substituents the lowest numbers
possible. If two or more side chains are in equivalent positions, assign the lowest number to the one
which will come first alphabetically.
4. If the same substituent occurs more than once, the location of each point on which the substituent
occurs is given. In addition, the number of times the substituent group occurs is indicated by a prefix (di,
tri, tetra, etc.).
5. If there are two or more different substituents they are listed in alphabetical order using the base
name (methyl, bromo,-oic acid, etc ). The only prefix which is used when putting the substituents in
alphabetical order is iso(meaning "branched") as in isopropyl or isobutyl.
6. If chains of equal length are competing for selection as the parent chain, then the choice goes in
series to the chain which has the greatest number of side chains.
7. A cyclic (ring) hydrocarbon is designated by the prefix cyclo- which appears directly in front of the
base name.
In summary, the name of the compound is written out with the substituents in alphabetical order
followed by the base name (derived from the number of carbons in the parent chain). Commas are
used between numbers and dashes are used between letters and numbers. There are no spaces in the
name.
Here are some examples:

4-methylpent-2-ene. & 2,4 dimethylhexane
Try to name the following

ISOMERISM
What is Isomerism?
Isomerism is the phenomenon in which more than one compounds have the same
chemical formula but different chemical structures.
Chemical compounds that have identical chemical formulae but differ in

properties and the arrangement of atoms in the molecule are called isomers.
Therefore, the compounds that exhibit isomerism are known as isomers.
TYPES OF ISOMERISM
There are two primary types of isomerism, which can be further categorized into
different subtypes. These primary types are Structural Isomerism and
Stereoisomerism. The classification of different types of isomers is illustrated
below.
STRUCTURAL ISOMERISM
Structural isomerism is commonly referred to as constitutional isomerism. The

functional groups and the atoms in the molecules of these isomers are linked in
different ways. Different structural isomers are assigned different IUPAC names
since they may or may not contain the same functional group
The different types of structural isomerism are discussed in this subsection.
1. Chain Isomerism
It is also known as skeletal isomerism. These isomers differ in their chain

arrangements or branched structures.
An example of chain isomerism can be observed in the compound C5H12, as

illustrated below.
2. Position Isomerism
The positions of the functional groups or substituent atoms are different in

position isomers.
Typically, this isomerism involves the attachment of the functional groups to

different carbon atoms in the carbon chain.
An example of this type of isomerism can be observed in the compounds having

the formula C3H7Cl.
3. Functional Isomerism
It is also known as functional group isomerism.
As the name suggests, it refers to the compounds that have the same chemical
formula but different functional groups attached to them.
An example of functional isomerism can be observed between alkanal and

ketones or between alkohol and ether.
Example
1. The compound with molecular formula C3H6O.has two functional isomers :

C2H5CHO and CH3COCH3
propanal and prop-2-one.

2.The compound with molecular formula C3H8O.has two functional isomers:
CH3CH2CH2OH and. CH3CH2OCH3
Propanol. Methaoxyethane
4. Metamerism
This type of isomerism arises due to the presence of different alkyl chains on each
side of the functional group.
It is a rare type of isomerism and is generally limited to molecules that contain a

divalent atom (such as oxygen), surrounded by alkyl groups.like in R-OR (ethers)
and R-COOR(esthers)
Example:
1. C4H10O has isomers such as :
Pentoxyethane (C2H5OC5H11) and ethoxypentane (C5H11OC2H5).
2.C6H12O2 has isomers such as:
Ethylbutanoate ( C2H5COOC3H7) and buthylethanoate( C4H9COOCH3)
5. Ring-Chain Isomerism
In ring-chain isomerism, one of the isomers has an open-chain structure whereas

the other has a ring structure.
They generally contain a different number of pi bonds.
A greater example of this type of isomerism can be observed in C3H6. Propene and
cyclopropane are the resulting isomers, as illustrated below.
Stereoisomerism
This type of isomerism arises in compounds having the same chemical formula
but different orientations of the atoms belonging to the molecule in three-
dimensional space.
The compounds that exhibit stereoisomerism are often referred to as

stereoisomers.
Geometric Isomerism
It is the existence of two or more compound with the same molecular formula but
geometry of their substituents. They are called cis (same side) and trans (opposite
side) isomers. It occur only in symmetrical alkenes. Symmetrical means that the
alkane can be divided into two equal parts
Optical Isomerisml
Compounds that exhibit optical isomerism feature similar bonds but different
spatial arrangements of atoms forming non-superimposable mirror images.
These optical isomers are also known as enantiomers.
Enantiomers differ from each other in their optical activities.
Dextro enantiomers rotate the plane of polarized light to the right whereas laevo
enantiomers rotate it to the left, as illustrated below.

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IUPAC NAMING OF HYDROCARBONS

Here are some examples:

Try to name the following

Chemical compounds that have identical chemical formulae but differ in

Structural isomerism is commonly referred to as constitutional isomerism. The

The different types of structural isomerism are discussed in this subsection.

It is also known as skeletal isomerism. These isomers differ in their chain

An example of chain isomerism can be observed in the compound C5H12, as

The positions of the functional groups or substituent atoms are different in

Typically, this isomerism involves the attachment of the functional groups to

An example of this type of isomerism can be observed in the compounds having

It is also known as functional group isomerism.

An example of functional isomerism can be observed between alkanal and

1. The compound with molecular formula C3H6O.has two functional isomers :

propanal and prop-2-one.

CH3CH2CH2OH and. CH3CH2OCH3

It is a rare type of isomerism and is generally limited to molecules that contain a

1. C4H10O has isomers such as :

Pentoxyethane (C2H5OC5H11) and ethoxypentane (C5H11OC2H5).

2.C6H12O2 has isomers such as:

Ethylbutanoate ( C2H5COOC3H7) and buthylethanoate( C4H9COOCH3)

In ring-chain isomerism, one of the isomers has an open-chain structure whereas

They generally contain a different number of pi bonds.

The compounds that exhibit stereoisomerism are often referred to as

These optical isomers are also known as enantiomers.

Enantiomers differ from each other in their optical activities.

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