MCAT Organic Chemistry Question 29: Answer and Explanation
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Question: 29
14. (2R,3S)-2,3-dihydroxybutanedioic acid and (2S,3R)-2,3-dihydroxybutanedioic acid are:
I. meso compounds.
II. the same molecule.
III. enantiomers.
- A. I only
- B. III only
- C. I and II only
- D. I and III only
Correct Answer: C
Explanation:
Draw out these structures. The two names describe the same molecule, which also happens to be a meso compound because it contains a plane of symmetry. These compounds are not enantiomers because they are superimposable mirror images of one another, not nonsuperimposable mirror images. These compounds are better termed meso-2,3-dihydroxybutanedioic acid:
