Advices For Studying Organic Chemistry

H

C

O OH

OH

(+)-Tartaric acid

HO C

C

H

CO 2 H

i) In 1951 J. M. Bijvoet, the director of the van’t Hoff Laboratory of the

University of Utrecht in the Netherlands, using X-ray diffraction, demonstrated

conclusively that (+)-tartaric acid had the absolute configuration shown

above.

6. The original arbitrary assignment of configurations of (+)- and (–)-glyceraldehyde
   was correct.
   i) The configurations of all of the compounds that had been related to one
   glyceraldehyde enantiomer or the other were known with certainty and were
   now absolute configurations.

5.15 SEPARATION OF ENANTIOMERS: RESOLUTION

1. How are enantiomers separated?
   
   
   1. Enantiomers have identical solubilities in ordinary solvents, and they have
      identical boiling points.
   
   
   2. Conventional methods for separating organic compounds, such as crystallization
      and distillation, fail to separate racemic mixtures.
   
   
   
   

5.15A PASTEUR’S METHOD FOR SEPARATING ENANTIOMERS

1. Louis Pasteur: the founder of the field of stereochemistry.
   
   
   1. Pasteur separated a racemic form of a salt of tartaric acid into two types of
      crystals in 1848 led to the discovery of enantioisomerism.