D
DenTony11235
WHich will decarboxylate first?
Sorry its sideways. It is heated of course.
Sorry its sideways. It is heated of course.
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- Mar 14, 2012
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You won't get something this specific on the DAT orgo section. It's all very straightforward, they're not trying to trick you. They may ask about a basic decarboxylation and that's it.
I wouldn't even know how to guess this, because the electron pushing we learn in orgo class isn't what really happens (where the carbonyl grabs the hydrogen, the oxygen double bonds to the carboxy group, and the carboxy group gives its electrons to make an alkene). It's just a nice way to represent it.
If I had to answer I'd say B, because the reaction supposedly doesn't happen in steps from what we learn but rather as a concerted reaction, so theres no benefit to a carbocation for stabilization in the middle of the reaction. It'd be better just to have a hydrogen there to minimize any steric strain.
Edit: But then you could say that A would be favored since the alkene would be more stabilized. There won't be anything that goes back and forth like this on the DAT, if you're wondering about this you're fine.
I wouldn't even know how to guess this, because the electron pushing we learn in orgo class isn't what really happens (where the carbonyl grabs the hydrogen, the oxygen double bonds to the carboxy group, and the carboxy group gives its electrons to make an alkene). It's just a nice way to represent it.
If I had to answer I'd say B, because the reaction supposedly doesn't happen in steps from what we learn but rather as a concerted reaction, so theres no benefit to a carbocation for stabilization in the middle of the reaction. It'd be better just to have a hydrogen there to minimize any steric strain.
Edit: But then you could say that A would be favored since the alkene would be more stabilized. There won't be anything that goes back and forth like this on the DAT, if you're wondering about this you're fine.
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