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Chapter 5: Q.36 (page 205)

a) Locate the stereogenic centers in the ball-and-stick model of ezetimibe (trade name Zetia), a cholesterol-lowering drug. (b) Label each stereogenic center as R or S.

Short Answer

Expert verified

A stereogenic center is a point in a molecule in which one carbon atom is bonded to four different groups of atoms. This carbon atom is considered to be asymmetrical in nature.

By interchanging any group on the asymmetrical carbon, it leads to the formation of a stereoisomer.

Step by step solution

01

Meaning of stereogenic centers

A stereogenic center is a point in a molecule in which one carbon atom is bonded to four different groups of atoms. This carbon atom is considered to be asymmetrical in nature.

By interchanging any group on the asymmetrical carbon, it leads to the formation of a stereoisomer.

02

Stereogenic centers in ezetimibe

The structure of the ezetimibe molecule is shown below:

It has three stereocenters, as shown in the above structure.

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Most popular questions from this chapter

Draw a meso compound for each of the following molecules.

a.

b.

c.

Label each pair of compounds as constitutional isomers, stereoisomers, or not isomers of each other.

How are the compounds in each pair related to each other? Are they identical, enantiomers, diastereomers, constitutional isomers, or not isomers of each other?

a.

and

b.

and

c.

and

d.

and

e.

and

f.

and

Artemisinin and mefloquine are widely used antimalarial drugs. A ball-and-stick model of artemisinin appears on the cover of this text.

  1. Locate the stereogenic centers in both drugs.
  2. Label each stereogenic center in mefloquine as R or S.
  3. What is the maximum number of stereoisomers possible for artemisinin?
  4. How are the N atoms in mefloquine hybridized?
  5. Can two molecules of artemisinin intermolecularly hydrogen bond to each other?
  6. What product is formed when mefloquine is treated with HCl?

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.

贬颁鈮-颁鈮-颁贬=颁=颁贬-颁贬=颁贬-颁贬=颁贬-颁贬2CO2H
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