Stereoisomerism

Stereoisomerism

Stereoisomerism

Overview of Stereoisomerism

  • 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.

  • It is split into two major kinds: geometric isomerism and optical isomerism.

Geometric Isomerism

  • 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.

  • Cis isomers are those where the two largest groups are on the same side of the double bond.

  • Trans isomers, on the other hand, have these groups on opposite sides of the double bond.

  • Geometric isomers often have different properties and reactivities.

  • An example of geometric isomerism can be seen in the molecules but-2-ene (cis and trans).

Optical Isomerism

  • 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.

  • Optical isomers are known as enantiomers.

  • A defining feature of optical isomerism is the presence of a chiral centre - a carbon atom with four different groups attached.

  • An example of optical isomerism can be seen in amino acids.

  • 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.

  • 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).

  • 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.