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Q,56

Expert-verified
Organic Chemistry
Found in: Page 209

Short Answer

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

a.

b.

c.

d.

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.

See the step by step solution

Step by Step Solution

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.

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

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.

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.

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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