Optical isomerism

• Stereoisomers?are molecules that have the same?structural formula?but have the atoms arranged differently in space
• There are two types of stereoisomerism
  • Geometrical (E/Z)
  • Optical

   

• A carbon atom that has?four different atoms?or?groups of atoms?attached to it is called a?chiral carbon?or?chiral centre
  • Chira comes from a Greek word meaning hand, so we talk about these molecules having a handedness

   

• Compounds with a chiral centre (chiral molecules) exist as two?optical isomers?which are also known as?enantiomers

A molecule has a chiral centre when the carbon atom is bonded to four different atoms or group of atoms; this gives rises to enantiomers

• The enantiomers are?non-superimposable?mirror images?of each other just like your left and right hand
• Their physical and chemical properties are?identical?but they differ in their ability to rotate?plane polarised light
  • Hence, these isomers are called ‘optical’ isomers

   

When unpolarised light is passed through a polariser, the light becomes polarised as the waves will vibrate in one plane only

• The major difference between the two enantiomers is that one of the enantiomers rotates plane polarised light in a?clockwise?manner and the other in an?anticlockwise?fashion
  • A common way to differentiate the isomers is to use (+) and (-), but there are other systems using d and l, D and L, or R and S

   

• These enantiomers are therefore said to be?optically active
• The rotation of plane polarised light can be used to determine the identity of an optical isomer of a single substance
  • For example, pass plane polarised light through a sample containing one of the two optical isomers of a single substance
  • Depending on which isomer the sample contains, the plane of polarised light will be rotated either clockwise or anti-clockwise by a fixed number of degrees

   

Each enantiomer rotates the plane of polarised light in a different direction