Question 16.58: The reaction of (2R,3R)-2,3-dimethyloxirane with aqueous aci......

The reaction occurs with inversion of configuration at the center of the conjugate acid of the epoxide attacked by the nucleophilic water. Attack at one carbon atom gives a product designated (2S,3R), and attack at the other carbon atom gives a product designated (2R,3S). However, the two centers in the diol product are equivalent, and thus only a single product, which is meso, obtained.