Stereochemistry Part 2 Solutions: #15

15.* (1993 1 4C) Which substances would you rather try to resolve into optical isomers (enantiomers)? Expain.

(S,S)-3,4-diaminohexane and (R,R)-3,4-diaminohexane

(R,S)-2,3-diaminobutane and (S,R)-2,3-diaminobutane are a meso compound. They are identical (rotation about the C-C bond changes RS to SR and vice versa), and therefore cannot be resolved into enantiomers.

(S,S)-3,4-diaminohexane and (R,R)-3,4-diaminohexane are non-superimposable mirror images, or enantiomers. They can be resolved.