$Which\; of\; the\; following\; compounds\; is\; a\; meso\; compound?$

• A. $2,3ext\{-\}dimethylbutane$
• B. $2,3ext\{-\}dibromopentane$
• C. $2,3ext\{-\}dibromobutane$
• D. $2,4ext\{-\}dibromopentane$

Answer: (C)

Verified step by step guidance

1. Step 1: Understand what a meso compound is. A meso compound is an achiral molecule that contains multiple stereocenters but has an internal plane of symmetry, making it optically inactive despite having chiral centers.
2. Step 2: Identify the stereocenters in each compound. Look for carbon atoms bonded to four different groups, which are potential chiral centers.
3. Step 3: Analyze the symmetry of each compound. For a compound to be meso, it must have at least two stereocenters and an internal plane of symmetry that divides the molecule into two mirror-image halves.
4. Step 4: Apply this to 2,3-dibromobutane. This compound has two stereocenters at carbons 2 and 3, and it can have a plane of symmetry if the substituents on these carbons are arranged such that one half of the molecule mirrors the other.
5. Step 5: Compare with the other compounds (2,3-dimethylbutane, 2,3-dibromopentane, and 2,4-dibromopentane). Check if they have the required stereocenters and symmetry. Typically, 2,3-dibromobutane is the one that fits the criteria for a meso compound.