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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

Which group in each pair is assigned the higher priority in R,S nomenclature?

  1. -CD3,-CH3
  2. localid="1648446360910" -CH(CH3)2,-CH2OH
  3. localid="1648447310055" -CH2Cl,-CH2CH2CH2Br
  4. -CH2NH2,-NHCH3

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

a.

b.

c.

Rank the following groups in order of decreasing priority.

  1. -F,-NH2,-CH3,-OH
  2. -CH3,-CH2CH3,-CH2CH2CH3,-(CH2)3CH3
  3. -NH2,-CH2NH2,-CH3,-CH2NHCH3
  4. -COOH,-CH2OH,-H,-CHO
  5. -Cl,-CH3,-SH,-OH
  6. -C≡CH,-CH(CH3)2,-CH2CH3,-CH=CH2

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

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

b. Certain carbon–carbon 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?
See all solutions

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