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Chapter 5: Q.17 (page 192)

Label the two stereogenic centers in each compound and draw all possible stereoisomers.

a.

b.

Short Answer

Expert verified

a.

stereogenic centers

b.

Step by step solution

01

Stereogenic center

The four different groups are bonded with a common carbon. The carbon point is known as stereogenic center.

02

Stereoisomers

The stereoisomers are the enantiomers or diastereomers. The enantiomers are non-superimposable mirror images, and the diastereomers are not part of mirror images.

The formula to calculate stereoisomers from stereogenic centers is:2n.

Where n is the stereogenic center number.

03

Explanation

a. The stereogenic centers in the given compound are 2 as shown below:

stereogenic centers

Therefore, the possible stereoisomers are 4, which are the non-superimposable mirror images as shown:

Stereoisomers

Stereoisomers

b. The stereogenic centers in the given compound are shown as:

Stereogenic centers

The possible stereoisomers are the non-superimposable mirror images as shown:

Stereoisomers

Stereoisomers

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Most popular questions from this chapter

a. Locate all the tetrahedral stereogenic centers in discodermolide, a tumor inhibitor isolated from the Caribbean marine sponge Discodermiadissoluta.

b. Certain carbon鈥揷arbon double bonds can also be stereogenic centers. With reference to the definition in Section 5.3, explain how this can occur, and then locate the three additional stereogenic centers in discodermolide.

c. Considering all stereogenic centers, what is the maximum number of stereoisomers possible for discodermolide?

Determine if each compound is identical to or an enantiomer of A.

a.

b.

c.

Draw all possible stereoisomers for each compound. Label pairs of enantiomers and diastereomers. Label any meso compound.

a.

b.

c.

d.

Like carvone, the two enantiomers of celery ketone smell differently. The R enantiomer smells like celery leaves, whereas the S enantiomer smells like licorice. Draw each enantiomer and assign its odor.

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.
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