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(25 [ts,) Fovice reusonable mechanisms fr each of the following reactions; Be certain l0 Use AITOW pushing (electrn pushing) and (0 include all intermediates. Ifan ...

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(25 [ts,) Fovice reusonable mechanisms fr each of the following reactions; Be certain l0 Use AITOW pushing (electrn pushing) and (0 include all intermediates. Ifan intermediate is Terceliice sthilized, be sure inelucle the most stable resonance contributor:ethanol"0*HzSO4heatH3cDsan

(25 [ts,) Fovice reusonable mechanisms fr each of the following reactions; Be certain l0 Use AITOW pushing (electrn pushing) and (0 include all intermediates. Ifan intermediate is Terceliice sthilized, be sure inelucle the most stable resonance contributor: ethanol "0* HzSO4 heat H3c Dsan



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Write a stepwise mechanism for each of the following reactions. Explain why a more stable alkyne (2-butyne) is isomerized to a less stable alkyne (1-butyne), but under similar conditions, 2,5-dimethyl-3-hexyne forms 2,5-dimethyl-2,3-hexadiene.

Okay, This is a very good practice problem. So we're essentially drawing resident structures for a second substitution onto nitrobenzene. So when I say second substitution, I mean, it's we're adding the second substantial into that Benzedrine but nitro group, already being the first substitution. So we have to do or thematic in Paris is gonna take a little time for me to draw, but so So basically, the whole exercise of this problem is that is to show, um, at least be familiar with the resident structures when you're resonating that carbo Kalyan within the ring by moving those double bonds around which carbo carry ons are going to be, um, most contributing to the overall reactivity. You would see with that type of with that type of intermediate when you have the addition at that site, right? So entertained that, um, nitro would give you Ah, the orthe the Ortho products rights. You have an electric file that's been added to the Ortho position. Now you can take the other two double bonds and you can push these electrons around. So I'm gonna be, um, right. So here's your nature of group. Sorry. I was such, um I've been trained to draw all those bonds. Um, when I draw a hexagon, right. So we just pushed it down here. So now you're gonna have the charge Will be here. And then, um, we could also push the electrons this way now double headed arrow for residents. So now I push that little bonds there. This one's still there. We have a real luxury file here and to um Right. So now you're positive charge is gonna be on the same carbon as that nitro group. Um, which is always a problem. So, um right. So which carbo candy on structure of the three that I drew here is going to be the least stable. So why don't you see a lot of Ortho products? Ah, when you do when you do ah, situation. Right. So really, it's this intermediate right here. So it's this rest in structure that contributes. Um, that that that explains why you don't see orthe Oh, um, substitution. Ah, a large amount of Ortho substitution with these strongly deactivating groups because you have a strong electron withdrawing group in the nature of group. Um, and you have a resident structure where you could put that positive charge right on the same carbon. And that's seriously high energy. That is a very high energy intermediate, Um, in the sense that you weren't early on and organic chemistry that that these Carbon Canyon's need electron donation from alcohol groups. Like the same explanation for why it's your share of carbon compounds are more stable because you have donation electrons, sharing and donation and hyper congregation from three other carbon atoms to give it some support. When you have a strong, electrolyte strong grip like that, you're going to destabilize um, the essentially the entire the entire series of intermediates through residents when you have or so that coal carbon Catalans gonna be destabilized and very high energy when you have addition at that orphan position. So, um, same thing with Para, Right? So entertain, um, addition here at the power position. So, um, I could take these electrons and I can push them up here like that. So now you have the 1st 1 I draw is gonna be the one that I, um, that I honed in on, right. So now I just resonated that positive charge onto the carbon I was talking about so this guy is the least stable. The most high energy resident structure that you can draw. Um, with the power product, that's the exact same structure. It's on the exact same structure as before, but it definitely, ah. Puts that positive charge. And the worst points it could be, um, right. And that I could push his watch, runs up, um, to make another among there. So here's your electron and 02 So now I moved there, and that's all right. I put one there. There we go. Sorry. Yeah, this is good. Make sure we're doing this right now. The positive charges is meta to the metro group, so that was not as bad, right? But all the resident structures, um, right, so that you could just resonate that cover caddy on around the ring. Um, and then the one I circled in red is gonna be the one that is the most high energy, which also dis favors attack or substitution at that power position. So you'll see that you won't necessarily see mom or stable. Um, you won't see one of those intermediates that we just drew putting that carbo caddy on, um, in a pretty unfavourable position with respect to the nitro group, you won't see any of those when you're when you're cycling through these meta possibilities here because you'll see when you cycle around that charge when you have the meta product here. So once you have, ah, substitution at that meta position and you form that carbo carry on, you're gonna have, um, you're able to spin this charge around without putting the cover carry on in a position where you're going to destabilize or raise the energy of the intermediate. Um, so it's not It's not really good language to say that these are, um these air favorable carbo caddy on structures. I mean, they are, but they're much lower in energy overall that either of the possibilities um ah, that you can draw with the orphan para substituted intermediates. So, overall, these meta intermediates are, um, are lower in energy compared to Ortho power, which is why you see, um, which is why you see a preference for the meta substituted product on nitrobenzene. Right? So now the the proton that's at this position can be easily be appropriated by some base. Um, and you'll reform or, um anticipates

Okay, So this is a question that talks about the residents forms of, um, a nitrate id benzene upon reaction with a second Electra file. Right. So, um, the last few pages before this question in the in the textbook on page 5 89 um, shows you the Ortho para and meta intermediates. Um, carro cada intermediates. Based on what? Um, based on what's of statuette you have on the ring already before you undergo nitrate shin and, um, it Hughes you in tow? What kind of things? You should look forward. Toa denotes something as being the least stable residents form of the most stable residents form. Right, So we're gonna go through some of those here. Um, now you know that nitrate Asian or that nitro groups are meta directing, right? So, um, you're going to see something that would ditch her addition at Ortho and para positions that you won't see with metta. So we're gonna do or thrown power first just so I could get that point across. So I'm gonna do my our pushing in red. So Right, So you're just gonna take those double bonds, you're gonna rotate them in the ring. Um So now we have this with your carbo cat ion. Um, at this position over here. Right? And now I can, um, move that one more carbon over. So now you have this snowdrop. It's really easy to mess up these arrows. Um, no, that's right. I'm not going crazy. Right? But the issue with So we're arrived at the problem, child. Right? So, um, these are the three main ones, right? So you'll notice that. So, you know, with Carbon Canyon's, they like to be stabilized by electron, um, groups that are willing to share or donate their electron density. Right. So that's why carbo carry ons that have, um, other carbons around it, like tertiary carver County ons are more stable than secondary for things like, um, hyper conjugation and stuff like that. Right. So, um, same reason here, except the reverse reasoning. Right. So having a carbon copy on directly on the same Adam the same carbon atom as a nitro group, which is one of the more strongly deactivating, strongly electron withdrawing groups, no one to chemistry known to chemists, it's going to seriously destabilize the intermediate and therefore, being that the residents form is kind of, like, an average of all contributing resident structures. Right. So this guy here is gonna be your least stable, um, your highest and energy, which is gonna deter addition off the electric file at the Ortho position because of the contribution from this residence form where you have the strong auto on donating group on the same Adam as your car will carry on. So you'll notice with the para. Um, all I have to do is move the double bonds over one, and you're going to arrive at the analogous. Ah, high energy intermediate here. Boom. Right there. So, um, same deal there, and then we have to draw all of them. So you're gonna move that double bonds? One more position. So now we have one here and here. And now the charge. Um, we just moved to now hydrate. Wrong. Sorry. I just do the same one twice. Um, still a bonds is going to be here. Sorry. Boom, boom area. So those are the three for the power. The power structure. Right. So you'll notice that you have these two destabilizing Thies too high energy residents forms that will deter addition of the Electra file. at the Ortho or power position. Um, And now? So why does Meta Why does it favor? Why is the favorite meta here? Right, So I'm gonna take this double bonds boom, boom. There's one. Move him over. There we go. She will notice that the residents forms of of the meta compounds have all of the charges in positions where, um, they're not being destabilized by an electron withdrawing group. So you still have the car back alley on near, um, an electron strong group, which is why the ring, um, which is why the all of the ring is is deactivated in general. Right. So these carbo Candiotti's air higher energy than would be on, um, if you have these carbon Catalans on, let's say Tom, you mean right? Let's say you were adding something to tell you in, um, together, all of these car battalions are higher in energy because you have in a lunchroom withdrawing group on the ring. Um, but the meta, uh, residents forms the ones that impossible. Don't have any, um, extremely high energy intermediates relative to the other contributing resident structures that are possible. Um, whereas Ortho in Para have that one form that I circled in red, where you could put the carbon caddy on which which first ability and for lowering and energy would require electron donation. Um, doesn't get that when you put the electron withdrawing group on the same Adam as those carbon Catalans.

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

The high definition off to middle to convene to my table to painting CFC exclusively extreme but no more temperature. This the alcohol. But when this reaction is done at 1. 60 yourself yes, the product obtained is my primary alcohol for middle one painting or one defendant we can reporting mechanism. Bye. The farmers of this product, right? Considering the reverse ability of these reactions these reactions at high temperature Okay, when the molecule is heated and do it lights and equilibrium between the following reactions which we're going right here, the Bs three adds to the double bond. The usual means 80 32. The one is having less number. So we have revealed a studio. Now this being reversible, this eliminates him or regular. We ate three. I can form the starting materials or it confirmed the double one on the other side. But this height is not so. They found this this module for the ads One more weird state on deserting the former self or X here home we need to hear and it's you again. The visibility of this reaction result in the generational. He's multitude Double one getting paid here. That is one highly missed last from desire involved in everyone. All these undergoes again additional great state. I'm back to serious in the beach to being added the terminal carbon which is a warm, stable intermediate What are convert on this on on solution? Yes, the primary alcohol. It is more stable at that temperature. So this is the mechanism by which the second poverty's found at Haider visit.


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