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Chapter 5: Q.10 (page 185)

Locate the stereogenic centers in each compound.

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Stereogenic centers

The point that gives rise to stereoisomers on the interchange of any two substituents attached to it is termed chiral centers or stereogenic centers.

Generally, in molecules involving carbon atoms, the stereogenic centers are the sp3hybridized carbon atom bonded to four different groups of atoms.

02

Stereogenic centers in cholesterol

The cholesterol molecules consist of eight chiral carbon centers and therefore have eight stereogenic centers

Stereogenic centers in cholesterol

03

Stereogenic centers in simvastatin

The simvastatin molecule consists of seven chiral carbon atoms and thus has seven stereogenic centers. The blue circles represent the stereogenic centers.

Stereogenic centers in simvastatin

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Most popular questions from this chapter

a. Label the four stereogenic centres in sorbitol as R or S.

b. How are sorbitol and A related?

c. How are sorbitol and B related?

Locate the stereogenic centers in each compound. A molecule may have zero, one, or more stereogenic centers. Gabapentin [part (d)] is used clinically to treat seizures and certain types of chronic pain. Gabapentin enacarbil [part (e)] is a related compound that is three times more potent.

a.

b.

c.

d.

e.

f.

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.

How is each compound related to the simple sugar D-erythrose? Is it an enantiomer,diastereomer, or identical?

a.

b.

c.

Locate the stereogenic centers in each drug.

a.

b.

c.
See all solutions

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