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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

What is the maximum number of stereoisomers possible for each compound?

a.

b.

c.

Draw the structures of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potant than any of its other isomers.

ethambutol

Label each stereogenic center as R or S.

a.

b.

c.

d.

e.

f.

g.

h.

Saquinavir (trade name Invirase) is a protease inhibitor, used to treat HIV (human immunodeficiency virus).

  1. Locate all stereogenic centers in saquinavir, and label each stereogenic center as R and S.
  2. Draw the enantiomer of saquinavir.
  3. Draw a diastereomer of saquinavir.
  4. Draw a constitutional isomer that contains at least one different functional group.

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

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