Which of the following names describes the relationship between these two structures?[Fill in the blank]

Question

BlackTom AI · Accepted Answer

A meso compound is achiral despite having stereocenters because an internal plane of symmetry makes the molecule superimposable on its mirror image. That key concept immediately identifies the relationship shown.

1. Relevant knowledge points and concepts
- A stereocenter (chiral carbon) has four different substituents.
- Enantiomers are non-superimposable mirror images (opposite configurations at all stereocenters).
- Diastereomers are stereoisomers that are not mirror images (they differ at some but not all stereocenters).
- Meso compounds have multiple stereocenters but an internal plane of symmetry, making the molecule achiral (one center is R, the other S in a two-center meso case).
- Constitutional isomers differ in connectivity (not the case here).

2. Step-by-step reasoning
- Identify stereocenters: the two central carbons each bear four different groups, so there are two stereocenters.
- Compare the two drawn structures: treat one as the mirror image of the other (or reflect one across a vertical plane). After reflection (or a 180° rotation in the plane of the Fischer projection), every substituent in the left structure matches the corresponding substituent in the right structure.
- Look for an internal mirror plane: the top and bottom substituents (OH groups) are the same and the left/right arrangement of the two bromines are opposite such that the whole molecule has a mirror plane through the central bond.
- Assign absolute configurations conceptually: one stereocenter will have R configuration and the other S. Because the configurations are opposite but the molecule bears an internal symmetry plane, the overall molecule is achiral.

3. Why the correct answer is correct
The two diagrams are stereoisomers that are mirror images but are superimposable due to an internal symmetry plane — the defining feature of a meso compound. They contain stereocenters but are achiral, so they are not enantiomers (which would be non-superimposable mirror images).

4. Why the other options are incorrect
- a. Enantiomers: would be non-superimposable mirror images; here the structures are superimposable because of internal symmetry.
- b. Diastereomers: would differ at some stereocenters but not be mirror images; these are related by mirror reflection and symmetry, not by partial stereochemical difference.
- d. Constitutional isomers: would have different connectivity; here connectivity is identical.

Conclusion: The relationship is a meso compound, matching the provided answer c. Meso compound.

Which of the following names describes the relationship between these two structures?[Fill in the blank]Single choice

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