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Chapter 5: Q,56 (page 209)

Draw all possible stereoisomers for each compound. Label pairs of enantiomers and diastereomers. Label any meso compound.

a.

b.

c.

d.

Short Answer

Expert verified

a. The stereoisomers of compound a are given below:

The meso compound of compound a is given below:

Pair A and B are enantiomers, and pairs A, C, and B, C is diastereomers.

b. The stereoisomers of compound b are given below:

This compound does not contain a meso compound.

c. The stereoisomers of compound c are given below:

The meso compound of compound c is given below:

d. This compound does not contain any stereoisomers.

Step by step solution

01

Enantiomers and Diastereomers

Compounds such as enantiomers and diastereomers belong to the class of stereoisomers. Enantiomers possess a single stereocenter, whereas diastereomers have several stereocenters.

02

Possible stereoisomers in compound a

a. The stereocenters in the compound a are marked as an asterisk in the figure given below:

Stereocenters in compound a

The possible stereoisomers in the compound a are given below:

Stereoisomers in compound a

In the compounds given above, the pair that contains A and B are enantiomers, and the pair having A, C, and B, C are diastereomers.

The compound C is a meso compound as it has an internal plane of symmetry.

The structure of the meso compound can be given below:

Meso compound of compound a

03

Possible stereoisomers in compound b

b. An asterisk represents the stereocenters of the compound b in the figure given below:

Stereocenters of the compound b

The possible stereoisomers of the compound b are given below:

Stereoisomers of the compound b

The compounds A, B, and C, D are enantiomers, and the compounds B and C are diastereomers. This compound does not possess a meso compound.

04

Possible stereoisomers in compound c

c. The stereocenter in compound c is represented as an asterisk in the figure given below:

Stereocenter in compound c

The possible stereoisomers of the compound c are given below:

Stereoisomers of the compound c

In the above compounds, B and C are enantiomers. The pairs A, B, and A, C are diastereomers.

The structure of the meso compound can be given as follows:

Meso compound of the compound c

The given compound is a meso compound as it contains an internal plane of symmetry.

05

Possible stereoisomers in compound d

d. The compound d does not contain any stereoisomers as they do not possess chiral centers.

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Most popular questions from this chapter

Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopenatane.

  1. How do the boiling points of A and B compare? What about A and C?
  2. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C.
  3. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?

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

a.

b.

c.

Draw all possible constitutional and stereoisomers for a compound of molecular formulaC6H12 having a cyclobutane ring and two methyl groups as substituents. Label each compound as chiral or achiral.

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?

Label each compound as chiral or achiral.

a.

b.

c.

d.
See all solutions

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