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Chapter 5: Q.21 (page 194)

Draw a meso compound for each of the following molecules.

a.

b.

c.

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

Meso compounds  

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

02

Achiral compounds

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

03

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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Most popular questions from this chapter

A sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S-adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.

A limited number of chiral compounds having no stereogenic centers exist. For example, although A is achiral, constitutional isomer B is chiral. Make models and explain this observation. Compounds containing two double bonds that share a single carbon atom are called allenes. Locate the allene in the antibiotic mycomycin and decide whether mycomycin is chiral or achiral.

HC≡C-C≡C-CH=C=CH-CH=CH-CH=CH-CH2CO2H

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

What is the maximum number of stereoisomers possible for a compound with:

a. three stereogenic centers;

b. eight stereogenic centers?

Explain each statement by referring to compounds A-E.

a. A has a mirror image but no enantiomer.

b. B has an enantiomer and no diastereomer.

c. C has both an enantiomer and a diastereomer.

d. D has a diastereomer but no enantiomer.

e. E has a diastereomer but no enantiomer.
See all solutions

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