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Topic: What is the mechanism?  (Read 3997 times)

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laotree

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What is the mechanism?
« on: August 10, 2005, 05:53:49 PM »
This reaction is" borrowed" from ecompound.com. I just wonder what is the mechanism of this every day reaction. The reaction makes your beer bitter.
 ???
« Last Edit: August 10, 2005, 05:54:45 PM by laotree »
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Re:What is the mechanism?
« Reply #1 on: August 10, 2005, 07:13:40 PM »
Looks a lot like an alpha-ketol rearrangement.  Here's my best guess.

The key is the migration of the red bond when the alcohol form the carbonyl.  The stereogenic hydrogen in the product can epimerize after the fact since it's still acidic.
« Last Edit: August 10, 2005, 07:17:07 PM by movies »
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