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Video Solution: Each of the following acid–base reactions involves sub...

Problem

Each of the following acid–base reactions involves substances found in Table 1.8. Use the pKa data in the table to help you predict the products of the reactions. Use curved arrows to show electron flow. Predict whether the equilibrium lies to the left or to the right and calculate the equilibrium constant for each reaction. 

 

Video Transcript

So now looking at this reaction here, we see a CH3 C double bond O, CH2, C, double bond O, CH3. So, do we have actually any acidic hydrogens here? we actually do, right? We've got two and we can pick one of them, we actually have two acidic hydrogens right here, okay? So, let me redraw this with our carbon here, like that, let me use some black, what we get is right here, right? When we've got two hydrogens, so what's going to happen guys is that this is going to come in here and grab this. Now, why is this acidic? Well, because it's actually next to a carbonyl, right? And its in between two carbonyls it's the Alpha carbon to two carbons, to two carbonyls, so we're actually going to get a pKa of about 10, okay? It's not exactly 10, it really depends on the molecule but if we can go ahead and approximate it to ten. Now, this next, what we're going to get next, right? Is our CH3, C, double bond O, CH. Now, with a negative charge and a lone pair on that carbon, which can resonate between the two carbonyls, which is why it's so acidic and then we have our methanol, okay? And we know that our methanol has a pKa of about 16, so we're going to go from more acidic to less acidic. So, in this case we're actually going to be going this way, right? this is about a million times more acidic than our methanol, okay guys? let me know have any questions especially about alpha carbon acidity, right? if not, let's move on.

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