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Chapter 5: Q.20 (page 194)

Which compounds are meso compounds?

a.

b.

c.

Short Answer

Expert verified

a. Meso compound.

b. Not a meso compound.

c. Meso compound.

Step by step solution

01

Meso compounds  

The compounds with atleast two stereogenic centers and a plane of symmetry are termed meso compounds.

The meso compounds are achiral.

02

Plane of symmetry  

There are two planes of symmetry as follows:

  • The horizontal plane of symmetry bisects the horizontal plane into two equal halves.
  • The vertical plane of symmetry bisects the vertical plane into two equal halves.
03

Explanation

a. The given compound has two stereogenic centers (as two centers have four different groups), and it has the same substituents with the same stereochemistry.

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 2 stereogenic centers (as two centers have four different groups), but it does not have the substituents with the same stereochemistry.

Therefore, a plane of symmetry does not exist in this compound. Hence, the compound is not a meso compound.

Not a meso compound

c. The given compound also has 2 stereogenic centers, and it has the same substituents with the same stereochemistry.

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

Meso compound with a vertical plane of symmetry

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Most popular questions from this chapter

Draw the structures of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potant than any of its other isomers.

ethambutol

The amino acid (S)-alanine has the physical characteristics listed under the structure.

a. What is the melting point of (R)-alanine?

b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?

c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?

d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?

e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.

Consider the ball-and-stick models of A-D. How is each pair of compounds related: (a) A and B; (b) A and C; (c) A and D; (d) C and D? Choose from identical molecules, enantiomers, or diastereomers.

a. Locate all the tetrahedral stereogenic centers in discodermolide, a tumor inhibitor isolated from the Caribbean marine sponge Discodermiadissoluta.

b. Certain carbon–carbon double bonds can also be stereogenic centers. With reference to the definition in Section 5.3, explain how this can occur, and then locate the three additional stereogenic centers in discodermolide.

c. Considering all stereogenic centers, what is the maximum number of stereoisomers possible for discodermolide?

What is the ee for each of the following mixtures of enantiomers A and B?

a. 95% A and 5% B

b. 85% A and 15% B
See all solutions

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