[tdod]

I am convinced its a mesomer and should be called cis-1,3-cyclopentanediol
My book however, says its called (1R,3S)-1,3-cyclopentanediol.

So, am I wrong or is it an error in the book?

Thanks!

[discodermolide]

It's name is (1R,3S)-cyclopentane-1,3-diol, and I would say it is a meso compound.
see http://masterorganicchemistry.com/2011/01/12/the-meso-trap/

[PhDoc]

What is the definition of a meso compound? Do meso compounds have chiral centers? If they have chiral centers, then how can they not be chiral?

Your compound has two chiral centers, however it is achiral due to a plane of symmetry bisecting the molecule, reflecting one half with the other half. If a compound has 6.022*10^23 chiral centers, however also has a sigma plane reflecting one HALF with the other half, then it is meso and hence achiral.

Please read... http://lennoxtutoring.com/2011/09/29/organic-stereochemistry-part-two/

A more interesting question is... can a compound with zero chiral centers be chiral and hence optically active?

[discodermolide]

Yes a compound with no chiral centers can be optically active. Think of the BINOL and BINAP series which have axial chirality.
http://en.wikipedia.org/wiki/1,1'-Bi-2-naphthol

[synthon]

It's name is (1R,3S)-cyclopentane-1,3-diol, and I would say it is a meso compound.

What distinguishes it from (1S,3R)-cyclopentane-1,3-diol?  Couldn't that also be the name of the listed compound?

[discodermolide]

It could be but I am not familiar with the exact rules for naming mess compounds.
Perhaps someone else knows?

[Dan]

Not 100% sure but I'd guess that given the choice the R centre gets priority over S and takes the lower locant.

[sjb]

It could be but I am not familiar with the exact rules for naming mess compounds.
Perhaps someone else knows?

No, well at least not strictly speaking. Just as bromo has priority over chloro, I think R has priority over S (see e.g. http://en.wikipedia.org/wiki/Cahn%E2%80%93Ingold%E2%80%93Prelog_priority_rules#Stereocenters:_R.2FS ) or similar

[fledarmus]

Here is a fairly clear description - http://teachers.lakesideschool.org/us/science/degrys/Stereoisomers.htm