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Chapter 5: Q.44 (page 207)

Draw both enantiomers for each biologically active compound.

amphetamine

(a powerful central nervous stimulant)

a.

ketoprofen

(analgesic and anti-inflammatory agent)

b.

Short Answer

Expert verified

a.

Enantiomers of amphetamine

b.

Enantiomers of ketoprofen

Step by step solution

01

Enantiomers of a given compound

A stereoisomer always has two enantiomers which are identified as the non-superimposable mirror images. The enantiomers are not identical to each other.

The two enantiomers of any compound are always different and remain different compounds even if the orientation of the molecule is changed.

02

To draw the enantiomers of the given compounds

The enantiomers of the given compounds can be drawn by the following steps:

  • In the given structure, locate the carbon atom, which is bonded to four different groups.
  • At the stereogenic center, two bonds are drawn in the plane of the page, which is represented by the normal lines.
  • One bond is drawn in front of the plane of the page, represented by the wedge.
  • One bond is drawn in the back of the plane of the page, represented by the dashed line.
  • Then the mirror image of the molecule is drawn. The mirror image gives the other enantiomer.
03

Enantiomers of the given compounds

a. The enantiomers of the compound amphetamine are drawn as shown in the following diagram:

Enantiomers of amphetamine

b. The enantiomers of the compound ketoprofen are drawn as shown in the following diagram:

Enantiomers of ketoprofen

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Most popular questions from this chapter

Which compounds are meso compounds?

a.

b.

c.

The amino acid (S)-alanine has the physical characteristics listed under the structure.

a. What is the melting point of (R)-alanine?

b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?

c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?

d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?

e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.

If the two stereogenic centers of a compound are R,S in configuration, what are the R,S assignments for its enantiomer and two diastereomers?

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.

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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