[aridavid5]

-Solved- Dunno how to delete/close

I'm asked to make a retro-synthetic analysis for the reaction mentioned in the title. I dunno if this it's a tip or a path to follow, but below the reaction is says: Synthesis: (alpha chlorination, elimination and Michael addition) Using this I figured the following:

Step1 - alpha chlorination: Add Cl2 and CH3COOH to get 2-chlorocyclopentan-1-one via acid catalyzed halogenation of the alpha carbon. I didn't go for the based promoted since it would result in both alpha hydrogen being replaced.

Step2 - elimination: Add NaOH to both neutralize the resulting HCl and to form cyclopent-2-en-1-one

Step3 - Michaels addition: I'm completely stuck here since I have no idea what I can use as the Michael's donor. I mean. I guess a primary carbanion of acetone might work, but is that even possible?

The link is a pdf of the structures: https://www.dropbox.com/s/j1690rsenhghvad/Retro-synthesis%201.pdf?dl=0