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How can cis-and trans-hydroxylation of c...

How can cis-and trans-hydroxylation of cis-2-butene be carried out ? Comment on the optical activity of the formed products.

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Osmium tetroxide adds to the double bond of cis-2- butene to form osmic ester which is hydrolysed by an aqueous ethanolic solution of sodium bisulphite. In this case, the two -OH groups get attached to the doubly bonded carbon atoms from the same side of the double bond and forms 1,2-diol. so, cis-hydroxylation takes place in case of this reaction. On the other hand, cis-2-butene reacts with peracids to form the corresponding epoxide. The resulting epoxide on hydrolysis with dilute acid or alkali yields 1,2-diol.
Epoxidation followed by hydrolysis causes addition of two -OH groups from the opposite sides of the double bond. so, trans-hydroxylation takes place in case of this reaction.
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