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ISOMERISM

The existence of two or more substances with the same molecular formula, but different
structures, is called isomerism. The structures are isomers. Since isomers are different
substances, they have different properties such as melting point, boiling point, etc.
There are several kinds of isomers:
a) structural (or skeleton isomers),
b) positional isomers
c) functional isomers
d) geometric isomers
1) STRUCTURAL (SKELETON) ISOMERS. They have different carbon chains, for example:

Molecular formula: C5H12
Condensed structural formulae:
CH3
|
CH3 – C – CH3
|
CH3
(neo pentane)

CH3 – CH2 – CH2 – CH2 – CH3
(pentane)

2) POSITIONAL ISOMERS. They are two compounds that differ only in the position of
something such as a double bond or an atom other than hydrogen and carbon (a functional
group), for example:

a) Molecular formula: C4H10O
Condensed structural formulas:
OH
|
CH3 – CH2 – CH2 – CH2

OH
|
CH3 – CH2 – CH – CH3

(1 butanol )

(2 butanol )

b) Molecular formula: C4H8
Condensed structural formulas:
CH2 = CH – CH2 – CH3
( 1 – butene )

CH3 – CH = CH – CH3
( 2 – butene )

ISOMERS. They are composed of the same atoms bonded in the same order. They are called “cis” and “trans” forms Example: Molecular formula: C4H8 Condensed structural formula: CH3 – CH = CH – CH3 Space arrangement: CH3 CH3 / CH = CH CH3 / CH = CH / CH3 .3) FUNCTIONAL groups. They have the same atoms arranged in different functional There are several pairs of functional groups that can be functional isomers: a) b) c) d) e) f) Aldehyde – ketone Alcohol – ether Carboxylic acid – ester Alkene – cycloalkane Alkyne – cycloalkene Alkyne – alkene with 2 double bonds Aldehyde – ketone CH3 – CH2 – CH = O O || CH3 – C – CH3 alcohol – ether carboxylic acid – ester CH3 – CH2 – CH2 – OH CH3 – CH2 – COOH CH3 – CH2 – O – CH3 CH3 – COO – CH3 alkene – cycloalkane Alkyne – cycloalkene CH3 – CH = CH – CH3 CH3 – C  C – CH3 CH2 – CH2 | | CH2 – CH2 CH = CH | | CH2 – CH2 4) GEOMETRIC ISOMERS. but with different arrangement of atoms around a double bond.

Cis 2-butene Trans 2. so the following pairs of formulae ARE NOT ISOMERS. they are the same compound: CH3 – CH2 – CH2 – CH2 | CH3 CH3 | CH3 – CH2 – CH2 – CH – CH3 CH3 – CH2 – CH2 – CH2 – CH3 CH3 | CH3 – CH2 – CH2 – CH | CH3 . so the following pairs of formulae ARE NOT ISOMERS.butene ( CH3 on the same side of the double bond ) bond ) ( CH3 in opposite sides of the double Tips to avoid making mistakes a) Carbon atoms chains can turn in a 180 ° angle. they are the same compound: CH3 – CH2 – CH2 – OH HO – CH2 – CH2 – CH3 CH3 – CH – CH2 – CH3 | Cl CH3 – CH2 – CH – CH3 | Cl b) The carbon atoms in a chain can bend the single bonds that join them.