Question 16.57: The reaction of (2S,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 of the secondary carbon atoms gives the (2R,3R) product, and attack at the other secondary carbon atom gives the (2S,3S) products. Thus, a racemic mixture of enantiomers results.