This is the answer to Chapter 20. Problem number 77 fromthe Smith Organic chemistry textbook. This problem says reaction of occitania with metal. Magnesium bromide followed by water, uh, forms a compound that shows a strong absorption in its eye. Our spectrum at 30. 632 100. Ah, and then we're given and it more data, um, and asked to draw the structure of the product into red a mechanism that illustrates the products formation. Okay, um and so the first thing to do here, eyes to look at this I r um, And hopefully we know by now on, I R peak between 32 3600 is gonna be from an alcohol from a no h I still even alcohol in this molecule. Um, okay. And then looking at the anymore data eso we have, Ah, 0.94 ppm. Triplet. That integrates to three. So that is gonna be a meth A group. Um, next to a methylene group, uh, our next signal eyes a multiplayer that integrates to two. So this is a methylene. The next signal also integrates the two. This is also probably a methylene group. We have a single it that integrates toe one a 2.24 p p. M. S. So I'm gonna tentatively say that this is the hydrogen on our alcohol. Ah, and then we have, ah, 3.63 ppm triplet. That integrates to two. So this is, um, another methylene. And I'm gonna say that this is the methylene that is bound to the alcohol. And that's why it's so far downfield, because it's d shielded by the alcohol. Um, and so looking at Aah these five signals that we have, um I'm going to say that the structure of our product is this. So, uh, one beautiful. Um, and then as far as, ah, a mechanism that illustrates its formation. I'll do that over here on the left. It's a pretty straightforward mechanism. So we have the occitania, um, metal. Magnesium bromide is going thio act his nuclear file and add to the carbon that's bound to the oxygen here. The carbon oxygen bond will break in. Those electrons will go to the oxygen. Ah, And so after that first step, we're here, um, with the alc oxide hoops. And so, uh, there is, of course, a negative charge here. Um, And then, uh, the water, The quenching step is just gonna protein ate that Alcock side that we just made. So rather than try to squeeze, squeeze it in right there, I'll put it down here. Okay, on. So there we go. There's the mechanism that accounts for this product. As I said, it's a pretty straightforward mechanism. Ah, and that's the answer to Chapter 20. Problem number 77.