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Despite of containing two stereocenters (chiral centers) meso-tartaric acid is not chiral, because it is not stereospecific in the center of the molecule as a whole.

A meso compound is superposable on its mirror image, and it does not produce a "(+)" or "(-)" reading when analyzed with a polarimeter.

For example, of the 3 possible isomers of tartaric acid (depicted in 'Related links'), there is one mesocompound (the 2R,3S and 2S,3R isomers are equivalent) and two other optically active stereo-isomeric forms:

dextrotartaric acid (L-(R,R)-(+)-tartaric acid) and

levotartaric acid (D-(S,S)-(-)-tartaric acid).

Only in the meso compound an internal plane of symmetry exists, bisecting the molecule which is not present in the non-meso compounds. That is, on rotating the meso compound by 180° on a plane perpendicular to the screen, the same stereochemistry is obtained.

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1w ago

Mesotartaric acid is optically inactive because it has a plane of symmetry that divides the molecule into two halves which are mirror images of each other, making the compound superimposable on its mirror image. As a result, the overall molecule does not exhibit optical activity.

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Q: Why is mesotartaric acid optically inactive?
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Related questions

An optically inactive amino acid is?

Glycine is an example of an optically inactive amino acid because it does not have a chiral center and therefore does not exhibit optical activity.


Write the name of optically inactive amino acid?

Glycine is an example of an optically inactive amino acid because it has a hydrogen atom as its side chain, which lacks a chiral center.


What is the chemical formula of mesotartaric acid?

C4H6O6


What is asymmetrical symmetry?

The synthesis of an optically active compound from an optically inactive compound with or without using an optically active reagent.


What is the difference between optical isomer and optically active isomer?

Optical isomers are those which have one or more asymmetric carbon atoms their optical activity means a tendency to rotate the plane of plane polarized light but some of such molecules have an internal symmetry as meso form of Tartaric acid , this is the optical isomer of Tartaric acid but is optically inactive.


What is A mixture of equal amounts of two enantiomers?

its called a racemic mixture and is optically inactive


Racemic mixtures and meso compounds?

A racemic mixture contains equal amounts of two enantiomers, resulting in no overall optical activity. In contrast, a meso compound is a molecule with chiral centers but possesses an internal plane of symmetry, making it optically inactive despite having stereogenic centers.


How do you distiguish for the optically active and in active?

First of all we should know what optically active molecules are "Those molecules which possess asymmetric(chiral) carbon atoms have the ability to rotate the plane polarized light(light of one wavelength having its electrical character vibrating in one direction only) to the left or to the right are known as Optically active molecules" while those molecules not following the former scenario are known as Optically Inactive molecules. All in all molecules having asymmetric carbon atoms are known as optically active molecules for example glucose(rotate plane polarized light to the left) & fructose(rotate plane polarized light to the right) are optically active molecules. While molecules lacking asymmetric carbon atoms are optically inactive molecules for example water is optically inactive. And that's how we can distinguish between these two molecular classifications.


What is difference between a racemic mixture and a meso compound?

A racemic mixture consists of equal amounts of enantiomers, resulting in no overall optical activity. A meso compound has chiral centers but is achiral due to an internal plane of symmetry, resulting in no optical activity.


Why meso compounds are optically inactive?

Meso compounds have a plane of symmetry that divides them into two identical halves. This symmetry ensures that any chiral centers in the molecule have corresponding mirror images that cancel out each other's optical activity. As a result, meso compounds are optically inactive overall despite containing chiral centers.


Are diastereomers optically active?

Diastereomers have different physical and chemical properties, and therefore can have different optical activities. Some diastereomers may be optically active, while others may not be. It depends on their specific molecular structures and whether they contain chiral centers.


The reaction of cis-2-butene with basic permanganate gives a product which is optically inactive even though it possess to chiral centresWhy?

The product is optically inactive because the reaction results in a meso compound, which has an internal plane of symmetry that makes it superimposable on its mirror image. This cancels out any optical activity in the molecule, even though it has two chiral centers.