Draw all possible stereoisomers for each compound. Label pairs of enantiomers and diastereomers. Label any meso compound.
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.
Compounds such as enantiomers and diastereomers belong to the class of stereoisomers. Enantiomers possess a single stereocenter, whereas diastereomers have several stereocenters.
a. The stereocenters in the compound a are marked as an asterisk in the figure given below:
The possible stereoisomers in the compound a are given below:
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:
b. An asterisk represents the stereocenters of the compound b in the figure given below:
The possible stereoisomers of the compound b are given below:
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.
c. The stereocenter in compound c is represented as an asterisk in the figure given below:
The possible stereoisomers of the compound c are given below:
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:
The given compound is a meso compound as it contains an internal plane of symmetry.
d. The compound d does not contain any stereoisomers as they do not possess chiral centers.
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?
94% of StudySmarter users get better grades.Sign up for free