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Chapter 5: Q.39 (page 206)

Label each compound as chiral or achiral.
a.
b.
c.
d.

Short Answer

Expert verified

Achiral.
Chiral.
Achiral.
Chiral.

Step by step solution

01

Meaning of chiral and achiral compounds

A molecule is classified as a chiral molecule if the mirror image of that molecule is not superimposable. The chiral molecule has two different stereoisomers, and these are known as enantiomers.

Achiral molecules are those molecules that have superimposable mirror images. The achiral molecules have a plane of symmetry or center of symmetry. The molecule having at least one stereogenic center is always chiral.

02

Identification of chiral and achiral compounds

The chiral and the achiral compounds can be identified by using the mirror plane. The structure of the molecule is drawn, and then the reflection of the structure is drawn. The molecule whose mirror image is superimposable is chiral.

a. The mirror image of the given compound is shown below:

Achiral molecule

The mirror image of the above molecule is superimposable. Hence, the above molecule is achiral.

b. The mirror image of the given compound is shown below:

Chiral molecule

This molecule is chiral because its mirror image is non-superimposable.

c. The mirror image of the given compound is as shown below:

Achiral molecule

The above molecule is also achiral in nature due to the superimposable mirror image.

d. The mirror image of the compound is as follows:

This molecule has a non-superimposable mirror image. It is chiral in nature.

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Most popular questions from this chapter

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.

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.

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

The [α] of pure quinine, an antimalarial drug, is –165.

a. Calculate the ee of a solution with the following [α] values: –50, –83, and –120.

b. For each ee, calculate the percent of each enantiomer present.

c. What is [α] for the enantiomer of quinine?

d. If a solution contains 80% quinine and 20% of its enantiomer, what is the ee of the solution?

e. What is [α] for the solution described in part (d)?

Give the IUPAC name for each compound, including the R,S designation for each stereogenic center.

a.

b.

c.

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