Stereoisomerism
Stereoisomerism
Stereoisomerism
Overview of Stereoisomerism
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Stereoisomerism is a form of isomerism where molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space.
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It is split into two major kinds: geometric isomerism and optical isomerism.
Geometric Isomerism
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Geometric isomerism, also known as cis-trans isomerism, occurs due to restricted rotation of molecules, often as a result of the presence of a carbon-carbon double bond or a ring structure.
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Cis isomers are those where the two largest groups are on the same side of the double bond.
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Trans isomers, on the other hand, have these groups on opposite sides of the double bond.
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Geometric isomers often have different properties and reactivities.
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An example of geometric isomerism can be seen in the molecules but-2-ene (cis and trans).
Optical Isomerism
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Optical isomerism is a form of stereoisomerism that occurs when a molecule can form two different configurations that are non-superimposable mirror images of each other.
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Optical isomers are known as enantiomers.
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A defining feature of optical isomerism is the presence of a chiral centre - a carbon atom with four different groups attached.
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An example of optical isomerism can be seen in amino acids.
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Enantiomers often have near identical physical and chemical properties except for the way they interact with plane-polarised light and react with other chiral molecules.
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A solution of one enantiomer will rotate the plane of plane-polarised light to the left (levo or l- isomer) and the other to the right (dextro or d- isomer).
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A 50:50 mixture of two enantiomers, known as a racemic mixture, does not rotate plane-polarised light as the two opposite rotations cancel each other out.