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Chapter 5: Q.8 (page 183)

Locate the stereogenic center in each compound and draw both enantiomers.

a.

b.

c.

Short Answer

Expert verified

The stereogenic centers in the given compounds and their enantiomers are represented below.

a.

b.

c.

Step by step solution

01

Stereogenic centers

The points in a molecule that could generate stereoisomers on interchanging two of the substituents attached to it are named stereogenic centers.

02

Enantiomers

The molecules whose mirror images are non-superimposable are termed enantiomers.

03

Stereogenic centers in the given molecules

The carbon atoms that are hybridized and are bonded to four other groups/atoms are stereogenic centers.

a. The given molecule consists of only one stereogenic center.

Stereogenic center in a

b. The given molecule consists of one stereogenic center.

Stereogenic center in b

c. The molecule consists of one stereogenic center.

Stereogenic center in c

04

Enantiomers of the given compounds

The enantiomers of the given compounds are provided below.

a.

Enantiomers of compound a

b.

Enantiomers of compound b

c.

Enantiomers of compound c

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Most popular questions from this chapter

An acid鈥揵ase 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.

Which group in each pair is assigned the higher priority?

a. -CH3,-CH2CH3

b. -I,-Br

c. -H,-D

d. -CH2Br,-CH2CH2Br

e. localid="1648296449951" -CH2Cl,-CH2CH(CH3)2

f.-CH2OH,-CHO

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?

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

a.

b.

c.

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?
See all solutions

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