Why isn't this Achiral?

[manohman]

D threw me off initially but I see now that it's achiral because it lacks any stereocenters.

But couldnt C be Achiral as Meso? Why wouldnt it be?

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[kraskadva]

Because by definition an achiral compound has no stereocenters and a meso compound has mirror image stereocenters reflected across a plane of symmetry.
So yes C is meso, but meso =/= achiral.

 

[gettheleadout]

Because by definition an achiral compound has no stereocenters and a meso compound has mirror image stereocenters reflected across a plane of symmetry.
So yes C is meso, but meso =/= achiral.

Your definition is incorrect. Achirality is a lack of net chirality; meso compounds are achiral by definition (source.)

C is not meso because it does not contain a plane of symmetry; the stereocenters both have absolute configuration of R.

 

[kraskadva]

I stand corrected.

 

[manohman]

Your definition is incorrect. Achirality is a lack of net chirality; meso compounds are achiral by definition (source.)

C is not meso because it does not contain a plane of symmetry; the stereocenters both have absolute configuration of R.

I see thanks guys.

So Achiral = lack of net chirality which is possible when you either have no chiral centers or a meso compound.

For C, if the Hydrogen and OH group off one of carbons were switched, so it had an R S configuration, that would make it meso right? So if you have two chiral centers, you either look for symmetry or the two chiral centers should have opposite stereochemistry.

^ Oh but that if there is a mirror plane/symmetry between two sides of a molecule with chiral centers, that implies that they would have opposite configurations, right?!

 

[gettheleadout]

I see thanks guys.

So Achiral = lack of net chirality which is possible when you either have no chiral centers or a meso compound.

For C, if the Hydrogen and OH group off one of carbons were switched, so it had an R S configuration, that would make it meso right? So if you have two chiral centers, you either look for symmetry or the two chiral centers should have opposite stereochemistry.

^ Oh but that if there is a mirror plane/symmetry between two sides of a molecule with chiral centers, that implies that they would have opposite configurations, right?!

Yes and yes!


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