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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

An acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products. How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers.

Label the stereogenic centers in paclitaxel, the chapter-opening anticancer drug, as R or S.

A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of water. What is the specific rotation of this compound?

Draw all possible stereoisomers for each compound. Label pairs of enantiomers and diastereomers. Label any meso compound.

a.

b.

c.

d.

The shrub ma huang (Section 5.4 A) contains two biologically active stereoisomers-ephedrine and pseudoephedrine-with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once popular combination drug used by body builders to increase energy and alertness, while pseudoephedrine is a nasal decongestant.

a. Draw the structure of naturally occurring (–)-ephedrine, which has the 1R,2Sconfiguration.

b. Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2Sconfiguration.

c. How are ephedrine and pseudoephedrine related?

d. Draw all other stereoisomers of (–)-ephedrine and (+)-pseudoephedrine and give the R,Sdesignation for all stereogenic centers.

e. How is each compound drawn in part (d) related to (–)-ephedrine?

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