(i) Suggest a mechanism for the conversion of cis-oct-4-ene to its corresponding epoxide (2,3-dipropyloxirane) followed by the ring-opening reaction to give the glycol, octane-4,5-diol. Account for stereochemistry. [Use a generic acid catalyst and peroxy acid.]
(ii) Do the above for trans-oct-4-ene.
(iii) Compare the products from (i) and (ii). Can the reaction sequence be identified as a stereospecific reaction?