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Solution: For each reaction below, draw the mechanism (curved arrows) ...

Question

For each reaction below, draw the mechanism (curved arrows) and then predict which side of the reaction is favored under equilibrium conditions.

Video Transcript

Alright, so let's go ahead and figure out our curved arrow mechanism for this reaction and then figure out in which direction is likely to proceed, alright? So, what we have here is water being deprotonated by this compound here, right? Which is just a deep protonated version of this guys, and this is our isopropyl alcohol, right? or isopropanol, you've probably seen it in your cabinets at home, and what happens here guys is that this, one of these lone pairs on the oxygen will come in, grab a hydrogen off of that water, either one it's exactly the same, right? And then kick electrons from this bond onto the oxygen, right? So now, what we end up with is this over here. And now we need to go ahead and figure out which direction the equilibrium will likely lie. So guys, what's the pKa of water? We know it's 16, right? What's the pKa of alcohol? ROH, right? It's going to be about 15.7 and we know that the way to figure this out, right? Is to just think about it, we're going to go from more acidic compounds to less acidic compounds, which means that we need to go from lower pKa to higher pKa. So, 15.7 is lower than 16, so our equilibrium is likely going to look something like that, right? if we're definitely going to be heading toward the left of the reaction. Alright guys, let's move on.

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