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Topic: Michael Additions  (Read 888 times)

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Offline wiseman

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Michael Additions
« on: November 08, 2020, 06:21:03 PM »
My goal is to provide a mechanism for an intramolecular Michael Addition. The reaction is as follows: C=CC(=O)CCC(C)(C)CCC1=CC(=O)C(C)(C)C1 reacted with NaOET over EtOH to give C123CC(C)(C)C(=O)C1CCC(=O)C2CC(C)(C)CC3

I am stumped, as I do not know whether I deprotonate the alpha carbon to the right of the first carbonyl group, or if I add the ethyl group to it. Once there, I still do not know how I am supposed to create multiple rings. Any and all help will be vastly appreciated.

Offline mjc123

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Re: Michael Additions
« Reply #1 on: November 10, 2020, 08:32:54 AM »
There isn't an ethyl group to add to anything. (Did you mean ethoxy?) Yes, you deprotonate that carbon. What does the resulting anion do next (hint: you yourself said "intramolecular Michael addition")? Draw the product of that reaction (before workup). What can that go on to do?

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