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Q.21

Expert-verified
Organic Chemistry
Found in: Page 194

Short Answer

Draw a meso compound for each of the following molecules.

a.

b.

c.

a.

b.

c.

See the step by step solution

Step by Step Solution

Meso compounds  

The meso compounds are an achiral type of compounds but contain two or more stereogenic centers (chiral centers).

Achiral compounds

The achiral compounds have a plane of symmetry or superimposable mirror images.

Explanation

a. The given compound has two stereogenic centers, and it has the same substituents with the same stereochemistry around each chiral center.

Therefore, a vertical plane of symmetry exists in this compound. Hence, the compound is a meso compound.

Meso compound with a vertical plane of symmetry

b. The given compound has only two stereogenic centers (as two centers have four different groups).

Therefore, a plane of symmetry exists in this compound. Hence, the compound is a meso compound.

Meso compound with a vertical plane of symmetry

c. The given compound has two stereogenic centers, and it has the same substituents with the same stereochemistry around each chiral center.

Therefore, a vertical plane of symmetry exists in this compound. Hence, the compound is a meso compound.

Meso compound with a vertical plane of symmetry

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