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Chapter 5: Q.7 (page 182)

The facts in Section 5.4A can be used to locate stereogenic centers in any molecule, no matter how complicated. Always look for carbons surrounded by four different groups. With this in mind, locate the four stereogenic centers in aliskiren, a drug introduced in 2007 for the treatment of hypertension.

Short Answer

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The stereogenic centers in aliskiren are:

Step by step solution

01

Stereogenic centres

Any atom/point present in a molecule that gives rise to isomers (stereoisomers) when atoms or groups connected to it are swapped is referred to as a stereogenic center.

02

Stereogenic carbons

Chiral carbons (i.e., the carbon atoms that are sp3hybridized and are connected to four different groups/atoms) are termed stereogenic carbons.

03

Stereogenic centers in aliskiren

The four carbon atoms that are sp3hybridized and are attached/bonded to four other groups give rise to four stereogenic centers in aliskiren.

Stereogenic centers in aliskren

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Most popular questions from this chapter

Locate the stereogenic centers in each molecule. Compounds may have one or more stereogenic centers.

a.

b.

c.

d.

e.

f.

Draw the enantiomer and a diastereomer for each compound.

a.

b.

c.

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 (鈥�)-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 (鈥�)-ephedrine and (+)-pseudoephedrine and give the R,Sdesignation for all stereogenic centers.

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

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?

Draw the mirror image of each compound. Label each molecule as chiral or achiral.

a.

b.

c.

d.
See all solutions

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