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Are the products of epoxide hydrolysis always going to be trans (when possible)? I did a...

Are the products of epoxide hydrolysis always going to be trans (when possible)? I did a problem where 4-methylcyclohexene became a trans 1,2 diol. We were asked to figure out if it underwent epoxide hydrolysis or KMnO4 in a basic solution. The books says it had to be epoxide hydrolysis because the product was trans. So my question is if this will always happen. Will the products of epoxide hydrolysis always be trans?

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Answer #1

If an alkene reacts with KMnO4 in mildly alkaline solution OR OsO4, the product is a cis-diol because both these reagents donate two O atoms from one side of the double bond.

However, if an alkene is converted to epoxide and then hydrolyses, the product is always a trans-diol because the nucleophilic attack by the incoming oxygen shall always occur from the side opposite to that of epoxide ring due to steric hindrance, resulting in the formation of a trans-diol, as illustrated below:

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