Which of these two pathways is better for Robinson cycloaddition?....

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Aristotelis1999
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Target molecule: 4-phenyl-2-cyclohexenone. 2-phenylacetaldehyde + 3-buten-2-one or 2-phenyl-2-propenal + acetone?
So this was a question on my orgII exam yesterday. The target molecule is 4-phenyl-2-cyclohexenone. By retrosynthetic analysis there is only one possible aldol condensation reaction, but two possible michael addition reactions afterwards. My "guess" was that the best one is 2-phenyl-2-propenal + acetone because in the other case the negative charge is delocalized throughout the benzene ring reducing the nucleophilic character of the a-carbon and also activating the ring in which case EAS could take place with the ring acting as the "Michael Donor". Please correct if I was supposed to post this question in another forum. Thank you a lot in advance.
 
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You need a base to generate the active enolate. Which enolate is easier to generate? Which one is more stable?
 
TeethWhitener said:
You need a base to generate the active enolate. Which enolate is easier to generate? Which one is more stable?
Well, there's an obvious answer for that. But anyway, I went and asked my teacher and it turns out the same exact exercise was solved in the textbook. The answer was what I said, but for very different reasons. Aldehydes undergo aldol condensation in base much faster than simple ketones. So, the issue with using the 2 - phenylacetaldehyde is aldol condensation with another same molecule as a side reaction.
 
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Very interesting. Good to know.