Advices For Studying Organic Chemistry

(Wang) #1
i) (+)-Tartaric acid is one of the by-products of wine making.


  1. Louis Pasteur’s discovery of enantioisomerism led, in 1874, to the proposal of the
    tetrahedral structure of carbon by van’t Hoff and Le Bel.


5.15B CURRENT METHODS FOR RESOLUTION OF ENANTIOMERS


  1. Resolution via Diastereomer Formation:

    1. Diastereomers, because they have different melting points, different boiling
      points, and different solubilities, can be separated by conventional methods..



  2. Resolution via Molecular Complexes, Metal Complexes, and Inclusion
    Compounds:

  3. Chromatographic Resolution:

  4. Kinetic Resolution:


5.16 COMPOUNDS WITH STEREOCENTERS OTHER THAN CARBON



  1. Stereocenter: any tetrahedral atom with four different groups attached to it.

    1. Silicon and germanium compounds with four different groups are chiral and the
      enantiomers can, in principle, be separated.




R^4 Si R^2

R^1

R^3

Ge R

R 2
1
R^4
R^3

N R

R 2
1
R^4
R^3

+
X−
O S R^2
R^1

2) Sulfoxides where one of the four groups is a nonbonding electron pair are chiral.
3) Amines where one of the four groups is a nonbonding electron pair are achiral
due to nitrogen inversion.
Free download pdf