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Solution: In each group of compounds below, select the most acidic com...

Question

In each group of compounds below, select the most acidic compound:

Video Transcript

Alright, so in this problem just like in the one, we're going to go ahead and figure out which one of these molecules into the most acidic, so let's go ahead and start labeling our pKaÕs. Here we know we don't just have a standard alkane at certain positions, right? At this position here and here, let me go ahead and highlight them in green in here, because we know that the oxygen makes the whole residence here, can give us a pKa, not a 50 like a standard alkane but we can get a pKa of about 20, right? Same thing goes for this carbon, in this carbon, so these is going to be roughly equal, so these are both going to be 20 as well, this one's also 20 symmetric molecule, but what about this next one? This next one doesn't have any hydrogen at the Alpha position, right? We have or two other carbon groups. So, really, we would be looking at the pKa's of these carbons here, which would just be about 50, maybe a little bit less because it would still slightly feel the pull from this oxygen but it still would not be anywhere near 20, and now, how about this last one? Well, this last one over here, let's go ahead and focus on our two carbon groups, right? Well, our two positions, we've got this one in green and then we've got this one in yellow, so the one in green is going to have our pKa of about 20, right? Because it's at the Alpha position of our ketone and guys, what about the yellow position? Not only do we have the oxygen pulling in the residents that can occur, we've also got these chlorine atoms and we know that we're going to have a dipole pulling from this yellow carbon in this direction, right? So, what we're going to get is not just our 20, but we're going to have something below 20, okay? So, our pKa is going to be less than 20, so it's going to be the most acidic carbon here in this molecule, and guys, it's actually going to be the most acidic carbon out of all of these molecules. So, right here this molecule, let me go ahead and have this purple, this one is our most acidic molecule, right? Let's move on.

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