Orgo bootcamp question

[pedtoothdoc]

hey! Quick question so in chads videos he said that adding a peracid (such as mcpba) to an alkene resulted in the anti addition of 2 -oh groups where the double bond was. However, I just took practice bootcamp test (orgo practice test 2) and it said that adding mcpba to an alkene forms an epoxide. Just wondering how you would be able to predict the product.

Thank you

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[predent2151]

Mcpba added to an Alkene produces an epoxide. However if Mcpba is added followed by h30+ you will get an anti addition alcohol. Why? Once you form the epoxide (through a mechanism you don't need to know) the oxygens lone pairs will attack the hydrogen on hydronium. This will put a positive charge on the oxygen. That's positive charge causes the oxygen from the newly formed water molecule to attack the carbon from the back opening up the epoxide forming anti alcohols. If this is confusing look up acid catalyzed epoxide openings.


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[pedtoothdoc]

Mcpba added to an Alkene produces an epoxide. However if Mcpba is added followed by h30+ you will get an anti addition alcohol. Why? Once you form the epoxide (through a mechanism you don't need to know) the oxygens lone pairs will attack the hydrogen on hydronium. This will put a positive charge on the oxygen. That's positive charge causes the oxygen from the newly formed water molecule to attack the carbon from the back opening up the epoxide forming anti alcohols. If this is confusing look up acid catalyzed epoxide openings.

Got it, thank you so much