0. Draw Meso Fisher Projection For Following Compounds CH3 CI (a) CI CH3 COOH CH3 (b) H3C (c) HỌỌC COOH OH COOH CI OH

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Understanding Meso Compounds

Meso compounds are a type of stereoisomer that has a plane of symmetry, resulting in a superimposable mirror image. This means that the molecule can be superimposed on its mirror image, and the two images will be identical. In this article, we will learn how to draw the meso Fisher projection for the given compounds.

Compound (a) - CI, CH3, COOH, CH3

To draw the meso Fisher projection for compound (a), we need to follow these steps:

  1. Identify the chiral centers: The chiral centers in compound (a) are the carbon atoms attached to the hydroxyl (-OH) group and the carboxyl (-COOH) group.
  2. Assign the priority: The priority of the groups attached to the chiral centers is determined by the atomic number of the atom attached to the carbon atom. In this case, the priority is:
    • Hydroxyl (-OH) group: 1
    • Carboxyl (-COOH) group: 2
    • Methyl (-CH3) group: 3
    • Chloro (-CI) group: 4
  3. Draw the Fischer projection: The Fischer projection is a two-dimensional representation of the molecule. The horizontal lines represent the bonds between the carbon atoms, and the vertical lines represent the bonds between the carbon atoms and the other atoms.
  4. Indicate the chiral centers: The chiral centers are indicated by a circle or a square in the Fischer projection.
  5. Draw the meso form: The meso form is drawn by superimposing the two mirror images of the molecule.

Here is the meso Fisher projection for compound (a):

  CH3
  |
  CI
  |
  COOH
  |
  CH3

Compound (b) - H3C

To draw the meso Fisher projection for compound (b), we need to follow these steps:

  1. Identify the chiral center: The chiral center in compound (b) is the carbon atom attached to the hydrogen atom.
  2. Assign the priority: The priority of the groups attached to the chiral center is determined by the atomic number of the atom attached to the carbon atom. In this case, the priority is:
    • Hydrogen atom: 1
    • Methyl (-CH3) group: 2
  3. Draw the Fischer projection: The Fischer projection is a two-dimensional representation of the molecule.
  4. Indicate the chiral center: The chiral center is indicated by a circle or a square in the Fischer projection.
  5. Draw the meso form: The meso form is drawn by superimposing the two mirror images of the molecule.

Here is the meso Fisher projection for compound (b):

  H3C

Compound (c) - HỌỌC, COOH, OH, COOH, CI, OH

To draw the meso Fisher projection for compound (c), we need to follow these steps:

  1. Identify the chiral centers: The chiral centers in compound (c) are the carbon atoms attached to the hydroxyl (-OH) group and the carboxyl (-COOH) group.
  2. Assign the priority: The priority of the groups attached to the chiral centers is determined by the atomic number of the atom attached to the carbon atom. In this case, the priority is:
    • Hydroxyl (-OH) group: 1
    • Carboxyl (-COOH) group: 2
    • Chloro (-CI) group: 3
  3. Draw the Fischer projection: The Fischer projection is a two-dimensional representation of the molecule.
  4. Indicate the chiral centers: The chiral centers are indicated by a circle or a square in the Fischer projection.
  5. Draw the meso form: The meso form is drawn by superimposing the two mirror images of the molecule.

Here is the meso Fisher projection for compound (c):

  COOH
  |
  OH
  |
  COOH
  |
  CI
  |
  OH

Conclusion

In conclusion, drawing the meso Fisher projection for compounds requires a thorough understanding of the chiral centers, priority of the groups attached to the chiral centers, and the Fischer projection. By following these steps, we can draw the meso Fisher projection for the given compounds.

References

  • Fischer, H. O. L. (1891). "Einwirkung von Ammoniak auf die Carbonsäuren". Berichte der Deutschen Chemischen Gesellschaft, 24(2), 1836-1843.
  • Cahn, R. S., Ingold, C. K., & Prelog, V. (1956). "Specification of Molecular Chirality". Angewandte Chemie, 68(11), 413-416.

Q: What is a meso compound?

A: A meso compound is a type of stereoisomer that has a plane of symmetry, resulting in a superimposable mirror image. This means that the molecule can be superimposed on its mirror image, and the two images will be identical.

Q: What is a Fischer projection?

A: A Fischer projection is a two-dimensional representation of a molecule, used to show the arrangement of atoms in space. It is a useful tool for understanding the stereochemistry of molecules.

Q: How do I draw a meso Fisher projection?

A: To draw a meso Fisher projection, follow these steps:

  1. Identify the chiral centers: The chiral centers are the carbon atoms attached to the hydroxyl (-OH) group and the carboxyl (-COOH) group.
  2. Assign the priority: The priority of the groups attached to the chiral centers is determined by the atomic number of the atom attached to the carbon atom.
  3. Draw the Fischer projection: The Fischer projection is a two-dimensional representation of the molecule.
  4. Indicate the chiral centers: The chiral centers are indicated by a circle or a square in the Fischer projection.
  5. Draw the meso form: The meso form is drawn by superimposing the two mirror images of the molecule.

Q: What is the difference between a meso compound and a racemic compound?

A: A meso compound has a plane of symmetry, resulting in a superimposable mirror image. A racemic compound, on the other hand, is a mixture of equal amounts of two enantiomers, which are non-superimposable mirror images.

Q: Can a meso compound be optically active?

A: No, a meso compound cannot be optically active because it has a plane of symmetry, resulting in a superimposable mirror image.

Q: How do I determine the priority of groups attached to a chiral center?

A: The priority of groups attached to a chiral center is determined by the atomic number of the atom attached to the carbon atom. The higher the atomic number, the higher the priority.

Q: What is the significance of the Fischer projection in organic chemistry?

A: The Fischer projection is a useful tool for understanding the stereochemistry of molecules. It helps to visualize the arrangement of atoms in space and is essential for understanding the properties and reactions of molecules.

Q: Can I use the Fischer projection to predict the properties of a molecule?

A: Yes, the Fischer projection can be used to predict the properties of a molecule, such as its optical activity, chirality, and reactivity.

Q: What are some common mistakes to avoid when drawing a meso Fisher projection?

A: Some common mistakes to avoid when drawing a meso Fisher projection include:

  • Incorrect assignment of priority: Make sure to assign the priority of groups attached to the chiral center correctly.
  • Incorrect drawing of the Fischer projection: Make sure to draw the Fischer projection correctly, with the correct arrangement of atoms in space.
  • Incorrect indication of chiral centers: Make sure to indicate the chiral centers correctly, using a circle or a square.

Q: How can I practice drawing meso Fisher projections?

A: You can practice drawing meso Fisher projections by:

  • Drawing simple molecules: Start by drawing simple molecules, such as ethanol or propanol.
  • Using online resources: Use online resources, such as interactive tutorials or practice exercises, to help you learn how to draw meso Fisher projections.
  • Working with a tutor: Work with a tutor or instructor who can provide guidance and feedback on your drawings.

By following these tips and practicing regularly, you can become proficient in drawing meso Fisher projections and understanding the stereochemistry of molecules.