I was reading the topic alcohol in that I saw a reaction Pinacol pinacolone rearrangement .

But I am not able to find the sterochemistry of the reaction .

Can anyone please tell me the stereochemistry enter image description here


1 Answer 1


The migrating group attacks trans to the leaving OH group:pinacol rearrangement stereochemistry

  • 3
    $\begingroup$ This answer implies a concerted mechanism, while the mechanism is usually written stepwise. Can you point us to papers that investigated the mechanism and came to this conclusion? As it stands, your answer seems claiming something without proving it. $\endgroup$
    – Jan
    Jun 4, 2016 at 11:32
  • $\begingroup$ Why in second mechanism it becomes five membered ring ? $\endgroup$
    – Koolman
    Jun 4, 2016 at 13:09

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