[UWSteve]

I was going over a practice quiz for my class, and I came across this problem.

Ethyl Butyrate + NaOEt  --------------->



I found it odd because my intuition tells me that OEt acts as a nucleophile and attacks the carbonyl carbon, but after that I kind of don't know which direction to go in.

I would think the other EtO group would end up leaving, but then that leaves us with what we started with, and that just seems like a dumb question to ask so I'm assuming something else happens.

[UWSteve]

Nevermind, I believe I figured it out. I believe this is just a claisen condensation.

[Yggdrasil]

Yup.  In this case it is important to use ethoxide as the base so that transesterification does not take place.

[UWSteve]

Yeah, I was just thrown off because we haven't gotten to this material yet (for some reason there wasn't a sample quiz for our chapter this week... went straight to next week), but I noticed the beta-dicarbonyl group and figured something was up.