orgo destroyer 2011 problem 242

[Adamsswag]

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I'd really appreciate it if someone can take a look at the Dieckmann condensation problem #242, and explain why in the solutions that specific alpha hydrogen is removed and why the other alpha hydrogen on the left side of the molecule (between the carbonyl and the carbon with the ethyl substituent) is not removed? I would think the alpha hydrogen on the left side that I just described is more acidic and more easily removed since the ethyl substituent provides more stability.

 

[Blue87Fiero]

I don't see why what you described wouldn't happen but at the same time its not an answer choice...at least I don't see it.

 

[Adamsswag]

I don't see why what you described wouldn't happen but at the same time its not an answer choice...at least I don't see it.

Very true! The way I described is indeed not an answer choice... In general I think it's a poor question. I appreciate you looking at the problem 🙂