Achiral Molecule with Multiple Stereocenters

A) Draw (2R,3S)-2,3-dibromobutane (above), using wedge/dash notation.

B) Identify each stereocenter in the molecule by drawing an asterisk next to the appropriate carbon atoms.

C) Re-draw the molecule by rotating the molecule so that the bromine atoms both point in the same direction (both wedges or both dashes).

D) Note that the molecule has an internal plane of symmetry. Draw the internal plane of symmetry in a second/separate drawing.

E) A molecule that contains stereocenters, but is achiral, is called a meso compound. Label this molecule as meso.