2
$\begingroup$

Are diasteriomers always optically active? If not then why? Though they are chiral then also.

$\endgroup$
2
  • 1
    $\begingroup$ @Mansi Jain because they might have elements of symmetry. $\endgroup$
    – user14857
    Commented Jan 28, 2016 at 14:35
  • $\begingroup$ If you carefully studied your book, you would have found an answer. $\endgroup$
    – Quark
    Commented Jan 28, 2016 at 20:18

1 Answer 1

6
$\begingroup$

Some definitions (by IUPAC):

  • Diastereomer: A stereoisomer that isn't an enantiomer.
  • Stereoisomer: An isomer that has the same bond connectivity, but arises due to differences in the spatial arrangements of atoms.
  • Enantiomer: Non-superimposable mirror image.

So, diastereomers do not necessarily have to be optically active. Consider cis- and trans-1,2-difluoroethene.

Difluoroethene

They are stereoisomers (connectivity is the same, but the fluorines are on opposite sides) which are not enantiomers (they aren't mirror images of each other), which makes them diastereomers.

Neither are chiral because they are superimposable on their respective mirror images. Equivalently, the presence of the plane of symmetry (which is the plane of the molecule) makes both isomers achiral.

$\endgroup$
7
  • $\begingroup$ I don't think this is correct. They are stereoisomers, which are not enantiomers, but that does not necessarily make them diastereomers. Usually a diastereomer would exhibit two chiral centres or more, but doesn't necessarily have to be an enantiomer e.g. mesotartaric acid $\endgroup$
    – Beerhunter
    Commented Jan 28, 2016 at 20:10
  • $\begingroup$ A diastereomer is just the same compound with one group twisted about a stereocentre,right? That does not necessarily mean diastereomers are those stereoisomers which are not enantiomers? This confused me. $\endgroup$
    – Quark
    Commented Jan 28, 2016 at 20:16
  • 3
    $\begingroup$ The IUPAC definition of a diastereomer is any stereoisomer that is not an enantiomer. goldbook.iupac.org/D01679.html @Beerhunter I could use meso-tartaric acid as an example too but the alkenes were simply easier. I may edit if I have the time later. $\endgroup$ Commented Jan 28, 2016 at 21:04
  • $\begingroup$ cc @Quark comment above Your definition is narrower than the correct definition. Compounds which differ in the configuration of some of their chiral centres are diastereomers, but diastereomerism is not restricted to that $\endgroup$ Commented Jan 28, 2016 at 21:06
  • $\begingroup$ @orthocresol Which other compounds are diastereomers then? $\endgroup$
    – Quark
    Commented Jan 29, 2016 at 5:46

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.