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The energy diagram corresponds to the SNL reaction of t-butyl bromide and ammonia (NH;). Which letters represent the carbocation intermediate and which represent tr...

Question

The energy diagram corresponds to the SNL reaction of t-butyl bromide and ammonia (NH;). Which letters represent the carbocation intermediate and which represent transitions states? Choose all that apply.kcallmolReactionIntermediate:Transition Statels:

The energy diagram corresponds to the SNL reaction of t-butyl bromide and ammonia (NH;). Which letters represent the carbocation intermediate and which represent transitions states? Choose all that apply. kcallmol Reaction Intermediate: Transition Statels:



Answers

Draw an energy diagram for the two propagation steps in the radical addition of HBr to propene. Draw the transition state for each step.

Drew an energy diagram for the addition off HB are toe 1 19 That's the energy versus reaction. Coordinate. Starting materials spirals through this point on that girl. Let one curve on your diagram. Show the information off one Brumer contain the curve on the left would respond to the formacion off one bomber contain, which is at this point, and the curve on the right will respond to the formacion off to rumor labour the positions off all reactions, intermediates and products. The positions for the reactors and products have been ordered labeled. This position is the intermediate reading through to vomit contain Um, this position is the intermediate leading toe. One Brumer contain the higher image of tropical time. Intermediate belongs to this curve. This image is hide in this one, and that's why the same curve has high in energy. Transition state Rich is this one. The curve explains why my karmic works and that to Mama Pimpin is that major product

Hell today we're doing Pumps forty six, of Chapter six, and this from were given this energy diagram small T step reaction and were given a few questions that were asked to solve. So in a weird given, they're asked how many steps in this reaction mechanism. So there's a few ways to determine how many steps a multistep reaction has from its reaction diagrams. So Step one. The easiest way is to identify hominy transition states. There are so remember transition state is your local energy maximum? So if you see here, we have a transition states one and then next local energy maximum. We have a transition state, too, and then the third transition states and she maximise this one trance state three. So the number of transition state equals the number of steps. So this is a three step reaction. But we can confirm this by doing another method, which is by identifying your reactions and your product of each reaction. So we going from react and returns, it should say to a product now, in the second reaction, the product of the first actually acts as the reactant for the second, and we go to this big activation energy barrier to the product number two, and then the product. Number two is I shouldn't be this reactions for reaction three going through his transition state to product. Three. So this is three reaction mechanism Label easily dealt age for each step, and the overall voltage each does age for the reaction. So overall daughter age is from the reactor number one. So we can say it's around here to the products of number three being right here. So this is a Delta h No for the reaction, not even determined that a true each step. So the reacting products seems that Delta H equals zero doesn't seem of the reaction approx of any energy difference. However, now for the seconds that the products is here and we're going down to the reactant, which is down here. So that's a Delta age. Her Step two. And this is a negative value. Sorry, positive value, because our product is higher energy than our starting material. So is the positive value on DH from number three. We see the product's down here. Reactions up here, so number three Prada reactions appear products down there. So Delta H here is negative for reaction three and overall is also going to be negative activation energy members. So that's from your reactions to your transition states. So the activation energy of number one is from your accident. Transition state. Here he's away. The actress Energy for Number two is from your reaction to transition. State for reaction, too. This is survey, and then for three. It's from the reactant o number three to the transition state. So it's going to be this one here. And then what else does it asked for us? So we identified the East of Aid without the age and the age now draw the structure transition state for each step and indicate its location on energy diagram. So joining structure of each step, we see that in transition State one think we are breaking our H i bond and we're actually forming. And new O. H. Bond hears you see reaction here in the product there. So for one job and black, remember, the transition state are in these big brackets with this double dagger arrow, and your bonds that are being formed and broken are dashes over breaking this. Ah, we're breaking this h I bond to form a new O H font. And if you recall our oxygen here is not gonna have three. Bonds can be positively charged for more positive in the product. So this means it's going to be a partial, positive transition state, and our item is gonna go from neutral to negative. So formal negative means that we're in a personal negative in a transition state. So this happens in transition statement. One transition state, too, which happens up here. Remember, energy Maximus is the place where bonds are being broken and forms are reacting, bones breaking product bonds of being formed and a lot is going on. It's very messy. That's why it's so high and energy. So from here, we're actually losing the carbon auction bond to make water fall off and generate a Carvel Catalan intermediate. So let's try that. So now our carbon all which to bond is falling off and prevent form water. So we know that Rayna from Carl Cat Down says positively charged, was any problem partial positive carbon and also our witch who was already formal charge positive, so could be also powerful. Positive charge here. Not getting double daggers has happened the treasures state to lastly transition. Stage three. We're having some sort of substitution or actually addition action to discover Catalan on reforming your C I bond. So this happens a transition state. Three. Now we're forming a new bond between I and see the iodine starts off. His negative says only partial negative in the transition state. The carbon starts off as a Carvel cat dancing, partial positive transition state and these air transition states. For this oral reaction, D asks us, What is the rate determining step and why will you write? The turning step is determined by your activities. Energy. The largest activation energy will be the slowest and the slowest. That will be your returning stuck. So obviously, if you're to measure these, we see that transition state to has the largest activation energy company to all others. So a second step going from this reactant to this product going through this transition state transition a too that is going to be a slow step, annual rate limiting step

This is the answer to Chapter 15. Problem number 55 from the Smith Organic Chemistry textbook on this problem asks us to consider this bro Emanation reaction of Turk beauty ain, um and were asked quite a bit about this reaction. Um, and so for part, A were asked to calculate the Delta h not by using the bond association energies and in table 6.2. Okay. And so I've drawn the reaction out here, so we need to look at what's happening. So this is a ch bond? Uh, broken. This is a br br bond broken. Ah. And so from that table 6.2, um, to break a ch bond is going to cost, uh, 381 killer jewels for mom to break a broom. Ebro mean bond is gonna cost, uh, 192 killed. Jules promote. And so when we add those together, uh, the left side of this reaction is going to require 573 killer jewels from all. So then, looking at the right side of this reaction, these air bonds being formed, So here we have a carbon rooming bond formed Ah, And so that is going to release 272 killer Jules promote. And here we have a hydrogen bro Ming Bond formed and that is going to release 368 killed, Jules. And so our total energy released on the right side is gonna be negative. 640 killer Jules. And when we add those values together, what we get is that the Delta h not for this reaction is going to be negative. 67 killed jewels from all. Okay, so this is an excellent, thermic reaction. Okay, s o negative. 67 killed. Jules, promote. All right, so that's part a. So, for part B. Ah, we're asked to draw a stepwise mechanism for the reaction, including all the steps. Um, okay, so this is, ah, free radical process. Uh, and so we're going to start with an initiation step. So that's what the eye is. Four eye for initiation. Uh, and so first thing that's gonna happen is that our bro me roaming bond is going to break when we heat this, and so we will get to Oops. We will get to bro. Mean radicals. Okay, so there's our initiation step propagation eyes going to be two steps. Um and so first will happen. Is this so the radical here, we'll form a new bond. So after this step, we'll have this with the radical on carbon here. Ah, and we'll also have some HBR. Okay. And then our second part of the propagation step is going to be, uh, the carbon radical that we just formed. It's going to react with an equivalent of bro me gas or ah, liquid bro. Mean as the temperature may dictate, um, so, like this, they will form a new bond will regenerate a booming radical here. Uh, and so after this step, we get our brominated product. Uh, and as I said, we regenerate a broom in radical here and then lastly, um, our termination step. It's gonna be when two radicals come together. Ah, And after the termination step, there's no more active radical species. And so that is why the reaction terminates. And so that can look like this So we could have any two radicals in this reaction. Um, but it's nice and clean to say that it's gonna be too, bro. Mean radicals coming together to reform br too. And so that terminates the reaction. Okay, uh, and so that is part B of this problem. For part C, you are asked to calculate a Delta h not for each propagation step. Okay, so we have to propagation steps. Um, and so this is gonna be, um we're gonna, uh, subtract the bonds formed from the bonds broken. Um, And so, um, from for the first propagation step, let's see, we're forming. Um, we're forming an HB our bond. So, um, let's say f so formed, uh, it's gonna be hbr. Uh, and that is worse. Um, negative. 368 on again. We're referencing part A for this or that. Table 6.2, So formed is gonna be negative. 368 killed Jules per mome. Ah, and broke in here in this step. So we'll say beef broken. Um, broken is gonna be a carbon hydrogen bond. So ch bond on, and that is gonna be worth 381. Killer. Jules Perma. Lt's positive. 3 81 killed Jules per mome. Ah. And so we add those two numbers together on Delta H. Not for this step is therefore going to be positive. 13 killer jewels from all okay. And we'll just do the exact same thing for the second step. So in the second step, we are forming a carbon rooming bond. And that is gonna be worth, uh, native 272 killer Jules per mole. Ah, and we are raking. Ah, a bro. Mean bro Ming Bond. And that is gonna be worse. Ah, positive. 192. Ah, And so when we had those two numbers together, the Delta h not for our second step, uh, is negative. 80 killed. Jules Prum, Ole. And so, actually, if you add those two delta H knots together, you get our negative. 67 killed, Jules per mole, which is the Delta h not of the entire reaction. Okay, um and so lastly, for Parts D and E, whereas to draw the structure of the trends are were asked to draw on energy diagram for the propagation steps and to draw the structure of the transition state of each propagation step. Okay, so I went ahead and did this because this is already quite a long answer on. This is a pretty time consuming thing to do. So here's the energy diagram. Um, it's it's showing Ah, how to get from Turk beauty mean we require 13 killed Jules promote to get to this carbon radical. Ah, and then forming the carbon bro. Me bond is going to release that that 80 killer Jules Prum Ole, which we calculated in the previous part of this problem. So there's the energy diagram with Transition State one in transition state to labeled on then over here on the right after on the two transition states. So remember, we used dashed lines for bonds that are breaking or forming a CZ part of this transition state. And we use adult a radical symbol to indicate, uh, where partial radicals are, uh, during this transition state. And so it was t s one nts to ah, and there they are. Um, and again, I just threw them out ahead of time because this is already quite a long answer. Eso There's parts D and E. Ah, Here are parts B and C again. Ah, And here is part, eh? Okay. And that's the answer to Chapter 15. Problem number 55

Let's show the structure of the carb Okada and intermediate that would be produced in each of the following reactions. For a we have ch three ch two c c h three bond ch ch ch three ch three at h p r And this will produce ch three ch two c ch three c h two ch ch three See it three plus you're minus. Come in Here. This is our carbo cat Ion Intermediate. And then this would produce ch three ch two c th three br ch two ch ch three ch three four Bromo to four Dimethyl hexane would be the product. And then for B, we have ch two ch three plus each eye. This would produce ch two ch three plus and I minus would come in here. This here is the carbo cat. I am intermediate. This would produce I ch two ch three one iota one apple cyclo tenting


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