Which of the following compounds can have a meso stereoisomer?

• A. $3_{-}$hexanol
• B. $2_{-}$3-dibromobutane
• C. $2_{-}$butanediol
• D. $2_{-}$chloropentane

Answer: (B)

Verified step by step guidance

1. Understand that a meso compound is an achiral molecule that contains multiple stereocenters and an internal plane of symmetry, making it optically inactive despite having chiral centers.
2. Identify the number of stereocenters in each compound. For a compound to have a meso form, it must have at least two stereocenters.
3. Analyze the structure of each compound to determine if it has an internal plane of symmetry. This involves looking for symmetry elements that make one half of the molecule a mirror image of the other half.
4. For example, in 2,3-dibromobutane, check if the two stereocenters at carbons 2 and 3 can be arranged so that the molecule is superimposable on its mirror image due to symmetry.
5. Eliminate compounds that either lack multiple stereocenters or do not have the required symmetry, concluding which compound(s) can have a meso stereoisomer.