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Optical Isomerism

The document discusses different types of compounds that can exhibit optical isomerism including allenes, biphenyls, and spiro compounds. Allenes show optical isomerism due to perpendicular p-orbitals resulting in one double bond being vertical and the other horizontal. Biphenyls are optically active when ortho substitution is present on both rings with different groups. Spiro compounds give non-superimposable mirror images when the groups on the sp3 hybridized central carbon are different.

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2K views2 pages

Optical Isomerism

The document discusses different types of compounds that can exhibit optical isomerism including allenes, biphenyls, and spiro compounds. Allenes show optical isomerism due to perpendicular p-orbitals resulting in one double bond being vertical and the other horizontal. Biphenyls are optically active when ortho substitution is present on both rings with different groups. Spiro compounds give non-superimposable mirror images when the groups on the sp3 hybridized central carbon are different.

Uploaded by

Dulce De
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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  • Optical Isomerism in Alkenes and Biphenyls
  • Optical Isomerism in Spiro Compounds

Optical isomerism is a type of stereoisomerism in which the isomers have the same molecular

formula and the structural formula but differ in their direction of rotation of plane-polarized
light. Biphenyls and allenes show optical isomerism without a chiral center.
Optical Isomerism in Allene: A consecutive diene or a cumulated diene is known as an allene.
The 3 carbon atoms in allene are doubly bonded, so the central carbon atom is sp hybridized
while the 2 carbon atoms on either side are sp2 hybridized. In 3-D, as the p-orbitals are at right
angles, the overlapping of perpendicular p-orbitals results in one double bond being vertical
while the other is horizontal. For allenes to exhibit optical isomerism, the 2 groups attached to
sp2 hybridized carbon must not be the same. However, they may or may not be identical to the
groups attached to the other sp2 hybridized carbon. This way, no plane of symmetry or center
of symmetry will exist and will make them optically active.

Optical Isomerism in Biphenyl: Biphenyls are formed by 2 benzene rings attached via a
single sigma bond. When biphenyl rings are substituted over the ortho position, the carbon
atoms in benzene are sp2 hybridised, thus the rotation across the sigma bond is restricted. Also,
to minimise steric hindrances, both rings lie perpendicular to each other. Optical activity in
biphenyls is observed when ortho substitution is present over both the rings and the groups are
not identical. Otherwise, a plane of symmetry will exist and it will become optically inactive.

Optical Isomerism in Spiro Compounds: Spiro compounds are made up of two rings attached
to a single carbon atom (spiro carbon atom), which is sp3 hybridised. This results in a
tetrahedral geometry which makes the 2 rings perpendicular to each other (non-planar in 3-D).
Spiro compounds thus give non-superimposable mirror images. For spiro compounds to exhibit
optical isomerism, the 2 groups attached to sp3 hybridized carbon must not be the same

The ring systems on either side of the central carbon atom may or may not be identical, but
they would still be optically active.

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