Meso compound?

[akimhaneul]

Why isn't this molecule a meso compound? Can't you draw a plane of symmetry from SH to oh?

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[averageasian]

SH and OH are not the same group, there is no symmetry in this molecule.

 

[DAT Destroyer]

Why isn't this molecule a meso compound? Can't you draw a plane of symmetry from SH to oh?

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Be careful here,,,,,,Fischer projections are always tricky....... If you get a Fischer, cut it in half horizontally. If the groups do not exactly match each other, it is NOT a meso compound . Even though this molecule is R at the OH carbon and S at the SH carbon, it is optically active and would not be a meso compound. This molecule would have 4 stereoisomers ,,,,,namely RS SR RR and SS. BTW......Just because a molecule has an element of symmetry does not imply it must be a meso compound.

Hope this helps.

Dr. Jim Romano