Which of the following compounds can have diastereomers?

• A. $1_{-}$propanol
• B. $2_{-}$butanone
• C. meso-$2_{,}{3}_{-}$dibromobutane
• D. $2_{-}$chlorobutane

Answer: (C)

Verified step by step guidance

1. Step 1: Understand what diastereomers are. Diastereomers are stereoisomers that are not mirror images of each other. They occur when a molecule has two or more stereocenters and differs in the configuration at one or more (but not all) of these centers.
2. Step 2: Identify stereocenters in each compound. For each compound, look for carbon atoms bonded to four different groups, which makes them chiral centers. For example, 1-propanol and 2-butanone typically have no or only one stereocenter, so they cannot have diastereomers.
3. Step 3: Analyze meso-2,3-dibromobutane. This compound has two stereocenters (at carbons 2 and 3). Because it is meso, it has an internal plane of symmetry, making it achiral but still capable of having diastereomers due to different configurations at these centers.
4. Step 4: Examine 2-chlorobutane. This molecule has one stereocenter (at carbon 2), so it can have enantiomers but not diastereomers, since diastereomers require at least two stereocenters.
5. Step 5: Conclude that only compounds with two or more stereocenters can have diastereomers. Therefore, meso-2,3-dibromobutane can have diastereomers, while the others cannot.