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Chapter 5: Q.3 (page 180)

Draw the mirror image of each compound. Label each molecule as chiral or achiral.

a.

b.

c.

d.

Short Answer

Expert verified

a. Achiral

b. Chiral

c. Achiral

d. Chiral

Step by step solution

01

Chiral molecule

Chiral molecules are the molecules that have “non-superimposable mirror images.”

Molecules having one stereogenic center are always chiral.

02

Achiral molecules

The molecules that have superimposable mirror images are termed achiral.

Achiral molecules have no stereogenic centers.

03

Chiral and achiral molecules

The mirror images of the given compounds are as follows:

a.

The mirror image of compound a

The mirror images are superimposable on each other and hence the compound is achiral.

b.

The mirror image of compound b

The given molecule consists of a stereocenter and its mirror images are non-superimposable.

Therefore, the compound is chiral.

c.

The mirror image of compound c

The mirror images are identical to each other and hence are superimposable.

Therefore, the compound is achiral.

d.

The mirror image of compound d

The given compound is chiral as it consists of a stereocenter (the carbon atom bonded to fluorine) and its mirror images are non-superimposable.

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Most popular questions from this chapter

What is the ee for each of the following mixtures of enantiomers A and B?

a. 95% A and 5% B

b. 85% A and 15% B

How is compound A related to compounds B–E? Choose from enantiomers, diastereomers, constitutional isomers, or identical molecules.

The shrub ma huang (Section 5.4 A) contains two biologically active stereoisomers-ephedrine and pseudoephedrine-with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once popular combination drug used by body builders to increase energy and alertness, while pseudoephedrine is a nasal decongestant.

a. Draw the structure of naturally occurring (–)-ephedrine, which has the 1R,2Sconfiguration.

b. Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2Sconfiguration.

c. How are ephedrine and pseudoephedrine related?

d. Draw all other stereoisomers of (–)-ephedrine and (+)-pseudoephedrine and give the R,Sdesignation for all stereogenic centers.

e. How is each compound drawn in part (d) related to (–)-ephedrine?

Rank the following groups in order of decreasing priority?

a.-COOH,-H,-NH2,-OH

b.-CH2CH3,-CH3,-H,-CH(CH3)2

c.-H,-CH3,-Cl,-CH2Cl

d.-CH=CH2,CH3,C≡CH,-H

Label each compound as R or S.

a.

b.

c.

d.
See all solutions

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