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Solution: For each pair of compounds below, identify the more acidic c...

Question

For each pair of compounds below, identify the more acidic compound:

Video Transcript

Alright, so let's take a look at these two molecules to figure out which one of them is more acidic. Over here we've got our acetone and then over here we've got diethyl butyl ether, right? Because we've got one, two, three, four carbons and there are two of them connected to our oxygen, right? So guys, this is actually a simpler one too, right? We know that this molecule here, we know these carbons right here and this one here, we know these both have pKaÕs of about 20, right? What about this guy? Well, sure we've got some atoms directly attached to the oxygen, right? So we should have a dipole and the inductive effect taking adding to the acidity, right? But guys, this one is directly attached to this carbon, right? Which we know is to have-, has an electron density being pulled by the oxygen, so that's a partial positive here and guys, if we remove this hydrogen, we can definitely go ahead and resume that negative charge this way, but here; first of all, is there even a hydrogen at this location? No, right? The only hydrogen's are at these locations, right? all of these, theyÕre equivalent. So guys, these, we know are probably going to have a pKa of about 50, okay? So, because they're almost standard alkanes, right? And here we couldn't even resonate if we wanted to we remove the hydrogen. So, guys this one is definitely going to take the higher acidity. Alright, let's move on.

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