How many stereoisomers of 2,3-butanediol, CH3CH(OH)CH(OH)CH3, exist?

How many stereoisomers of 2,3-butanediol, CH3CH(OH)CH(OH)CH3, exist? Correct Answer 3

2,3-Butanediol has two chirality centers but the sets of four substituents on each chirality center are identical. Each chirality center can have either an S or R configuration. The (2R,3R) and (2S,3S) compounds are enantiomers of one another, but the structures drawn as (2R,3S) and (2S,3R) compounds are identical (this is the achiral meso compound), so there are only three different stereoisomers. For a compound with n chirality centers there is the possibility of a maximum of 2n stereoisomers. However, if the sets of four substituents on each chirality center are identical there will be fewer than 2n stereoisomers.
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