Guess the Mechanism help (Organic Chemistry)

AI Thread Summary
The discussion centers on determining the mechanism for converting a diol into a ketone through spectral analysis. The initial hypothesis involved tautomerization, where oxygen atoms donate electrons to form a double bond, but this approach was unsuccessful. Ultimately, the solution identified is the pinacol rearrangement, which was not covered in lectures. This realization highlights the challenge of applying theoretical knowledge to practical problems in organic chemistry. Understanding the pinacol rearrangement is crucial for grasping the conversion process in this context.
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"Guess the Mechanism" help! (Organic Chemistry)

Homework Statement


After identifying my reactants and products via spectral analysis, I am now tasked with figuring out the mechanism behind converting a diol into a ketone.

Homework Equations



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The Attempt at a Solution


The key to this appears to be tautomerization somewhere in the reactant (whereby the oxygen atoms donate electrons in order to create a double bond), but everything I've tried with that has failed so far. I'm really stuck.
 
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