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Thought I would share this with you all trying to relearn your orgo.
For a compound to be meso, it needs to have an EVEN number of chiral centers about the axis of symmetry.
Additionally, let's take for example a pentane (5 chain carbon). For this compound to be meso, chiral centers must be on carbons 2 and 4, or 1 and 5. Chiral centers positioned on any other pairs of carbons (ex. 2 and 3, or 1 and 4) will not make the compound meso.
Lastly, a compound that is meso has opposite absolute configurations on its chiral centers. In the example above of pentane, if carbons 2 and 4 were chiral, they must have opposite absolute configurations i.e. R/S or S/R. Having S/S or R/R will not make that compound meso as it will not be symmetrical.
Hope this helps!
For a compound to be meso, it needs to have an EVEN number of chiral centers about the axis of symmetry.
Additionally, let's take for example a pentane (5 chain carbon). For this compound to be meso, chiral centers must be on carbons 2 and 4, or 1 and 5. Chiral centers positioned on any other pairs of carbons (ex. 2 and 3, or 1 and 4) will not make the compound meso.
Lastly, a compound that is meso has opposite absolute configurations on its chiral centers. In the example above of pentane, if carbons 2 and 4 were chiral, they must have opposite absolute configurations i.e. R/S or S/R. Having S/S or R/R will not make that compound meso as it will not be symmetrical.
Hope this helps!
