IIT JEE , AIEEE Forum - Chemistry , Organic Chemistry

madhusudan.chavan

Per acids act like electrophiles and the reaction is believed to proceed by the electrophilic addition mechanism for C=C.
The peracid would initially form an epoxide; the epoxide ring can be opened by acids or bases to from trans-1,2-diols.
In the acidic medium, the oxygen atom of the epoxide ring gets protonated and the attack of the watermolecule occurs from the side opposite to the oxygen atom to form trans-1,2-diol.
In case of an unsymmetrical epoxides, the attack of nucleophile occurs at the more substituted carbon atom since the +I effect of the alkyl group tends to disperse the +ve charge in the transition state.
Thus in the present case the the OH groups should be trans. Here we have not considered the reaction(if any) of peroxide with carbon carbon triple bond outside the ring.

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