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Which of the following compounds can also exist as a meso form?

1. 2,3-Dichloropentane
2. 2,3-Dichlorobutane
3. 2-Chlorobutane
4. 2-Hydroxypropanoic acid

Correct answer: 2,3-Dichlorobutane

Solution

2,3-Dichlorobutane (CH3-CHCl-CHCl-CH3) has two identical stereocentres, so it has a meso form with an internal mirror plane. 2,3-Dichloropentane has two different stereocentres (the two halves are not equivalent), so it cannot be meso.

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