isomerism
DESCRIPTION
ISOMERISM. A property in which two or more compounds having the same molecular formula but different arrangements of atoms in a structure……………. Isomers – are compounds with the same molecular formula but having different - PowerPoint PPT PresentationTRANSCRIPT
ISOMERISM
A property in which two or more compounds
having the same molecular formula
but different arrangements of atoms
in a structure…………….
Isomers – are compounds with the
same molecular formula but having different
structural orientations. Note: isomers do not necessary share similar properties unless
they belong to one family.
CLASSIFICATIONS
ISOMERISM
STRUCTURAL
STEREO
OPTICAL
GEOMETRICAL
CONFORMATIONAL
FUNCTIONAL
POSITIONAL
CHAIN/SKELETAL
Structural Isomerism
or sometimes called constitutional isomers is defined as isomers that
vary in the bonding attachments of atoms.
3 TYPES
Skeletal • Skeletal Isomers – Isomers
that differ in the arrangement of the carbon chain. Example : C6H14
CH3CH2CH2CH2CH2CH3Hexane
-------------→
CH3CHCHCH3
│CH3
│CH3
-------------→ 2,3 - dimethylbutane
Example Pentane, C5H12
Expanded
Condensed
Positional• Positional Isomers – Isomers
that differ in the location of a noncarbon group or a double or triple bonds. Example :CH3 – CH ═ CH – CH3 ---------→ 2 - butene
CH2 ═ CH – CH2 – CH3 -------------→ 1 - butene
Example C3H7Br
Functional •Functional Isomers –
Isomers with structural differences that place them in different classes of organic compouds. Example : C2H6O
CH3 – CH2 – OH -----------→ ALCOHOL
CH3 – O – CH3 -----------→ ETHER
Example C3H6O
Stereoisomerism
Isomers with the same bonding attachments of
atoms but different spatial orientations.
3 TYPES
Geometric• Or sometimes called cis and trans isomers – a type of stereoisomerism in
which atoms or groups display orientation
differences around a double bond or ring.
Example
Cis - Isomer• Geometric isomer in which
groups are on the same side of the ring or double bond.
Example : 1,2 – dichloroethane
C ═ C
Cl Cl
H H
Trans – Isomer
• Geometric Isomer in which groups are on the opposite sides of ring or double bond.
Example : 1,2 - dichloroethane
C ═ C
Cl
Cl
H
H
Conformational•Isomers that differ
as a result of the degree of rotation around a carbon – carbon single bond.
2 Kinds
“ECLIPSED”• The highest energy conformation
corresponds to a structure in which the hydrogen atoms are "eclipsed.“
• Geometric isomer in which conformation around carbon – carbon single bonding which attached atoms are as close together as possible.
“ECLIPSED” Ethane
“STAGGERED”• The lowest energy
conformation is a structure in which the hydrogen atoms are "staggered“
• Conformation around a carbon – carbon single bond in which attached atoms are as far apart as possible.
“STAGGERED” Ethane
Difference
eclipsed staggered
“BOAT” CONFORMATION
“CHAIR” CONFORMATION
optical• Isomers that are
identical in structure except where they
differ as mirror images.
Example
Example
Example
• Isomerism was first noticed in 1827, when Friedrich Wohler prepared cyanic acid and noted that although its elemental composition was identical to fulminic acid (prepared by Justus von Liebig the previous year), its properties were quite different.
• This finding challenged the prevailing chemical understanding of the time, which held that chemical compounds could be different only when they had different elemental compositions.
• After additional discoveries of the same sort were made, such as Wohler's 1828 discovery that urea had the same atomic composition as the chemically distinct ammonium cyanate, Jöns Jakob Berzelius introduced the term isomerism to describe the phenomenon.
• In 1849, Louis Pasteur separated tiny crystals of tartaric acid into their two mirror-image forms. The individual molecules of each were the left and right optical Stereoisomer, solutions of which rotate the plane of polarized light in opposite directions.
FIN