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Write stcpwist rraction mechanisms fur tht following reaction Lhe space belov;. Carefully consider the stereochemistry ofthe starting material and tht product (12 p...

Question

Write stcpwist rraction mechanisms fur tht following reaction Lhe space belov;. Carefully consider the stereochemistry ofthe starting material and tht product (12 points})HONaOH Ho

Write stcpwist rraction mechanisms fur tht following reaction Lhe space belov;. Carefully consider the stereochemistry ofthe starting material and tht product (12 points}) HO NaOH Ho



Answers

Intramolecular aldol cyclization of 2,5 -heptanedione with aqueous NaOH yields a mixture of two enone products in the approximate ratio $9: 1 .$ Write their structures, and show how each is formed.

We have the following structure and we would like to know what would the resulting product to be if we performed a need to elimination reaction on it. So an important thing to remember with the elimination reactions is that we need the beta hydrogen to the alkali hair life in the alcohol light to be anti per player to each other. But in this situation here we see that our hydrogen and our alcohol life are on the same side and they do not exhibit ante para planner geometry. But a cool thing that we can do here is that we can rotate this carbon carbon Boss such that it will make them exhibit anti airplane or geometry. And it will look like this. It's the same structure, just with carbon carbon bond flipped. So these bonds here gonna remain the same? Well, the ethanol of the FL Group Rather is gonna be in the plane of the screen. Our hydrogen is now coming towards us and the method group, it's going away from us. Here. We see that the reacting beta hydrogen and the chlorine are now on opposite sides to each other and eggs of anti fair planner geometry so we can go out and perform Ari to elimination reaction, which is one step. So we have. Our base comes in and deep. Roenick's hydrogen electrons get pushed to this bond, which pushes this clearing out. And we get the following structure here and we want to go ahead and science terry chemistry to this structure so we can assign priority for looking at the Left carbon. Here we see that the Effort group has priority over the Method Group and on this side that the final group aspirin, over the hydrogen group. And since the prior two groups are on opposite sides to each other, we would say that they are that they exhibit the E configuration.

This problem. We need to show how these two creating react and decide whether it's an s and one mechanism. Orin s into mechanism in the products. You have to show a specific Syrian chemistry if it exists. So the first need to safe is to identify what kind of a light it isthe. So this is a primary hey light, meaning that it's only going to react by innocent to mechanism. This is also a strong nuclear file. But since primary Alka highlight, it's going to react. Ryan s into you so it attacks in a concerted step, attacking the carbon and kicking out believing group in the same stuff. And our product is this. If this were a story of center, it would, er invert the stereo chemistry. But it's not so we don't have to worry about that party in part B. Our re agents are not in the days I and I am. So once again, you identify what kind of alcohol light it is, and this is secondary so it can do Ehsan one or s into. So then you look at the nuclear file and it's a strong nuclear file. So instead of favoring us in one at favors s and two. So once again it attacks in the conservatives. Concerted fashion, attacking in, kicking out, believing group in the same stuff and s into reactions. Invert the stereo chemistry where it was attacked. So you get this product and just make sure to pay attention to the serious industry there and seeing are free agents are ends this so once again, you identify what kind of awful Hey, light it is. This one is for Sherry, so it can only react by an s in one mechanism. The nuclear file is also weak, which favors us in one. But it's going to react right in s and one anyway because of her, she agrees he life. So the first step in and everyone reaction is federal assis. So the leaving through please by itself and then the nuclear file attacks is both front word in backward attack. But since there's no stereo stereo center here, uh, it form was one product, and the last death is a proton transfer between the substrate and another molecule of the solvent for nuclear file. In this case, that's consistent with the leveling effect because the strongest acid that can exist in solution is the person to call it So our final product for this one? Yes. This and the impregnated solve it or d. Our reaction is, and our nuclear file is water. Okay, so once again, you identify the Alfa. Highlight this awful Hey, light is also a tertiary, so it can only react fine. Us in one stuff. Nuclear file being weak also favors. And us in one reaction. So the first step, they meaning girl, please. And it produces a plane or caramel cat. I, um And in the next step, the CIA file attacks from front, side and back side. So it formed. Yeah, yes. Plus, it's the name TMR and Auntie Em are just means that the wedge in the dash were switched. And in the last step, another proton transfer occurs between the product and solve it. Hey, So our final product even my immediate about unequal mixture of both this and it's an anti armor because it was an essene. One reaction. You get receiving mixture of products

This is the answer to Chapter 27. Problem number 53 from the Smith Organic Chemistry textbook. Ah, and this problem were given ah, starting material and a product that it's converted to. And we're told that this happens by two sequential parasite. Quick reactions. And so we're asked to show them and to account for the observed stereo chemistry. Okay, s. So the first thing that's gonna happen is gonna be a, um these four pi bonds, um that are in this molecule are going to Ah, do? Ah, Conroe Auditory Electra cyclic ring opening. Um, and so that is going to look like this on. I guess it's not four pi bond. It's four electron pairs, since that is a signal bond. Right there. Um, so the electrons are gonna move like this. Okay, um, And so now, after that first step, we'll have this bear with me while I draw it because it's kind of a weird looking molecule. Okay, now, Okay. Um, so this would be our intermediate after the first, uh, parasitic quick reaction. So again, there was a con Rhoda Torrey Electric cyclic ring opening. Okay. And so we're forming for pie bombs. um all right. And so this pi bon is gonna be easy on this one is going to be e. Um, And so now we're gonna have a dis Rhoda Torrey. Uh, rain closure on Only three of the four pi bonds that we formed are going to participate this time. So again, this one was con Rhoda Torrey. Ah, and the 2nd 1 is going to be dis Rhoda Torrey on the 2nd 1 is going to proceed like this. So here, here and here. Okay, um and so our product after that is going to be 26 members rings okay. With double bonds here, here and here. Um, and we will get this stereo chemistry again as a result of the stereo chemistry in our intermediate and the fact that this is a dis Rhoda Torrey Paris stick. My green closure. Okay, uh, and so that is the answer to Chapter 27. Problem number 53

This is the answer to Chapter 27. Problem number 54 from the Smith Organic Chemistry textbook on this problem. Eyes asking us to go from these two starting materials to this product by a series of to Paris cyclic reactions. Um, And so obviously, we have to two different molecules coming together to form a single molecule. Um, the first thing we should think is Psychlo addition. Um, and the most common cycle auditions really that we've talked about have been, um, four close to Psychlo additions. Um, and so we can look at all this and sort of think. Okay, well, how can we get from where we are To where we could set up a four plus to Psychlo addition. Um, and so the answer is our first para cyclic reaction, because again, we were told that there are two s o. R. First Paris. A quick reaction could be a new Electra cyclic ring opening on this, uh, this psych lobe beauty mean starting material. So if we do our Electra cyclic ring opening, um, use use some heat because he eats what we're given in the problem. Um, and so Oops. So we end up with something that looks like this. And this, of course, is a great substrate with which to do, uh, like it deals all their type four plus two Psychlo audition. Um, and so were also asked to account for the stereo chemistry in this final product. And so a cyclo addition A thermal for close to cycle addition like we're talking about here. Eyes going to be super facial, Um, and so we can draw the movement of the electrons. I probably should shit of, uh, sure drawn this flipped so that it lined up a little better. But, um, so be like that, Like that, Um, And so that's going to get us to, uh, this final product that we're looking for And again, um, the stereo chemistry that were asked to account for eyes going to be because, um, the four plus two thermal cycler addition eyes a super facial reaction. So there we g o. And so there is our final product that we were asked to make on. So the two parasitic quick reactions that we're talking about are gonna be an electro cyclic ring opening on, then a four plus to Psychlo addition. Um and so that's the answer to Chapter 27. Problem number 54


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