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Topic: Stuck on a (condensation?) mechanism...  (Read 719 times)

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Offline zyu2ranger

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Stuck on a (condensation?) mechanism...
« on: August 17, 2020, 09:01:57 AM »
Hello. I am struggling with a problem. I have attached it. I cannot rationalize a reasonable mechanism for the transformation of the reactant to the production shown. The initial problem is given at the top of the image. Thank you for any assistance.

I have tried to protonate the -OH group and then have an enol kick out the water to form a carbocation; I've tried to make the enol at the top of the right ring make a 1,3-dicarbonyl and close the ring on the carbon adjacent to the initial OH group... none of these are working. Please assist! Thank you in advance.

Offline kriggy

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Re: Stuck on a (condensation?) mechanism...
« Reply #1 on: August 18, 2020, 03:40:07 AM »
Forming the enol seems like a good idea but I dont see how it could kick the water. Something else leaves. Maybe try numering the atoms and figure out where they end up

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