Meso-Tartaric acid

Definition

meso-Tartaric acid is a type of tartaric acid that has a plane of symmetry, making it an achiral molecule. It is a dicarboxylic acid with two hydroxyl groups, and its molecular structure exhibits a meso configuration, which means it has two chiral centers but is optically inactive.

5 Must Know Facts For Your Next Test

1. meso-Tartaric acid has two chiral centers, but the molecule as a whole is achiral due to the presence of a plane of symmetry.
2. The two hydroxyl groups in meso-Tartaric acid are arranged in a trans configuration, which results in the molecule being optically inactive.
3. Unlike the two enantiomeric forms of tartaric acid (D-tartaric acid and L-tartaric acid), meso-Tartaric acid does not rotate the plane of polarized light.
4. meso-Tartaric acid is commonly used as a food additive and in the production of certain pharmaceuticals.
5. The achiral nature of meso-Tartaric acid is a result of its specific molecular structure and the arrangement of its functional groups.

Review Questions

• Explain how the molecular structure of meso-Tartaric acid contributes to its achiral nature.
  • The meso-Tartaric acid molecule has two chiral centers, but the presence of a plane of symmetry in its structure makes the molecule as a whole achiral. This is because the two chiral centers are arranged in a way that the molecule can be superimposed on its mirror image, resulting in an optically inactive compound. The specific arrangement of the hydroxyl groups and carboxyl groups in the trans configuration is what gives meso-Tartaric acid this unique symmetrical structure.
• Describe the key differences between meso-Tartaric acid and the enantiomeric forms of tartaric acid (D-tartaric acid and L-tartaric acid).
  • Unlike the enantiomeric forms of tartaric acid, which are chiral and optically active, meso-Tartaric acid is achiral and optically inactive. This is because the meso compound has a plane of symmetry that allows the molecule to be superimposed on its mirror image, whereas the enantiomers of tartaric acid are non-superimposable. As a result, meso-Tartaric acid does not rotate the plane of polarized light, while the D- and L-tartaric acid enantiomers exhibit opposite rotations of polarized light.
• Evaluate the significance of the achiral nature of meso-Tartaric acid in its practical applications, such as in the food and pharmaceutical industries.
  • The achiral nature of meso-Tartaric acid is particularly important in its practical applications. Since meso-Tartaric acid is optically inactive, it does not interact with or interfere with chiral compounds, making it a useful food additive and pharmaceutical ingredient. This property allows meso-Tartaric acid to be used in a wide range of products without affecting the activity or properties of other chiral molecules present. Additionally, the lack of optical activity means that meso-Tartaric acid can be used without concerns about potential enantiomeric impurities, which is crucial for maintaining the quality and consistency of the final products.

Related terms

Tartaric Acid:

Tartaric acid is a dicarboxylic acid found in many fruits, especially grapes, and is a byproduct of wine production. It is a chiral molecule with two chiral centers.

Chirality:

Chirality refers to the property of a molecule that is not superimposable on its mirror image, resulting in the existence of two non-identical, non-superimposable forms called enantiomers.

Meso Compound:

A meso compound is a molecule that has two or more chiral centers but is achiral due to the presence of a plane of symmetry, making it optically inactive.