Chirality: Fischer projection

Excursion 1/3
 

The Fischer projection is a schematic representation of a chiral molecule that for some purposes obviates perspective drawings.

The conventions are as follows:

  • In a Fischer projection the compound's C chain is written vertically [usually with the most oxidized carbon atom on top (e.g. -COOH, if present; for an aldose the aldehyde group -CHO)].

  • The remaining substituents at each carbon are written with horizontal bonds.

  • At each asymmetric carbon atom the vertical bonds are to be imagined behind the paper plane, the horizontal ones in front of the paper plane.

  • The internal carbon atoms often are not written.

  • H atoms as substituents often are not written.

  • A hetero atom bonded to the lowermost asymmetric C atom attributes to the compound a D- or an L-label (from Latin dexter, right, and laevus, left).

Examples:


L-alanine
=  
 

 
  =
 

 

 

(S)-alanine
             

D-threose
=
 

 
=
 

 

 

The example D-threose nicely demonstrates a characteristic of the Fischer projection: It describes a molecule in its extremely unrealistic all-eclipsed conformation of the main chain, see the Newman projection at the right and the sawhorse projection left to it.







 
 
  (c) Lehrstuhl für Mathematik II Universität Bayreuth