Stereochemistry

Configurational (stereo) isomers

Exercise 5

    

a) Draw the spatial stuctures of the enantiomers of 2,3-dihydroxypropanal. The asymmetric C atom will be the center of each tetrahedral structure shown. b) Which group of organic substances such compounds belong to? c) Give the appropriate Fischer formulas and decide if they are D or L forms d) Represent the enantiomers by Newman formulas looking in the direction C(2) - C(3). e) Give the names in R S of the enantiomers. (Priority: $CHO$ $\gt$ $CH_2OH$) f) In treating enantiomer R with fuming hydrochloric acid, we find that the dichloro product obtained has no optical activity. Interpret!

If treated with fuming HCl the racemic mixture of two enantiomers is obtained by nonstereospecific nucleophilic substitution (SN1):

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