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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

Without drawing out the structures, label each pair of compounds as enantiomers or diastereomers.

a. (2R,3S)-hexane-2,3-diol and (2R,3R)-hexane-2,3-diol

b. (2R,3R)-hexane-2,3-diol and (2S,3S)-hexane-2,3-diol

c. (2R,3S,4R)-hexane-2,3,4-triol and (2S,3R,4R)-hexane-2,3,4-triol

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

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

Label each stereogenic center as R or S.

a.

b.

c.

d.

e.

f.

g.

h.

Amygdalin, a compound isolated from the pits of apricots, peaches, and wild cherries, has been used as an unsanctioned anticancer drug both within and outside of the United States. One hydrolysis product formed from amygdalin is mandelic acid, used in treating common skin problems caused by photo-aging and acne.

a. How many stereogenic centres are present in amygdalin? What is the maximum number of stereoisomers possible?

b. Draw both enantiomers of mandelic acid and label each stereogenic centre as R or S.

c. Pure (R)-mandelic acid has a specific rotation of 鈥�154. If a sample contains 60% of the R isomer and 40% of its enantiomer, what is [伪]of this solution?

d. Calculate the ee of a solution of mandelic acid having [伪] = +50. What is the percentage of each enantiomer present?
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