Orgo Question from AAMC 4 (139)

[ridethecliche]

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Start with acetoacetic ester and want to make 3 ethyl 2 pentanone from it by adding ethyl iodide.

I can add the first R group (ethyl) by doing an enolate rxn on the ester side of the compound, but I'm not sure how to add the 2nd R group on there and make the carbonyl+ester group leave.

It's like this reaction: http://uk.ask.com/wiki/Acetoacetic_ester_synthesis

but you want to add another R' where there already is one, which works because there's an alpha hydrogen there, but you want the rest of the 'stuff' to leave. I can't figure that out mechanistically and I've looked over a textbook as well.

Add in R' two and acid wash? How would that get rid of it?

Question states that the reagent is alkylated, saponified, acidified, and pyrolyzed.

 

[ridethecliche]

Slept on it and now I think that both R groups add, then the product is saponified leading to the salt.

Heat and H+ lead to decarboxylation. Tada!