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2. 4 (4 points) Show the mechanism of the acid-catalyzed hydration of 3-methylbut-[-(4 points) The procedure outlined in part methylbutan-2-ol, Give two reasons why...

Question

2. 4 (4 points) Show the mechanism of the acid-catalyzed hydration of 3-methylbut-[-(4 points) The procedure outlined in part methylbutan-2-ol, Give two reasons why.the not be the best way to synthesize 3 -3-Methylbuian-2-0l

2. 4 (4 points) Show the mechanism of the acid-catalyzed hydration of 3-methylbut-[- (4 points) The procedure outlined in part methylbutan-2-ol, Give two reasons why. the not be the best way to synthesize 3 - 3-Methylbuian-2-0l



Answers

Dehydration of trans-2-methylcyclopentanol with POCla in pyridine yields predominantly 3 -methylcyclopentene. Is the stereochemistry of this dehydration syn or anti? Can you suggest a reason for formation of the observed product? (Make molecular models!)

Defecation off or degradation anymore. You know what if I welcome according to work from the hydraulic? Did I mean his 100? Let me millions. This involves Well, you have fun with it. I said you can hurt, right? See? That's three. See number? Oh, t o the instant. So you know better on this. But yet today company You I earned him. I think you guys want he said a list subsequent today. A sin deviation off the boxing. Yeah. No, as he did a on have chose the photo I palpable make you. You see You see all to need The mortar, the setting Indie promotional The sign of a room. See full days. See, we're born again. Rest CS three see no holes.

On the white board. You see that we have 33 dime Ethel one view teen, and it goes through an asset catalyzed hydration reaction to form 23 dime Ethel Too beautiful. And so we're going to write a mechanism for this. And so the first thing that we start off with is this double bond on the beauty mean well attack for lack of a better word the hydrogen on the H three oo plus and then thes electrons that are shared by the hydrogen oxygen. That bone is broken in those electrons go to the oxygen, which makes oxygen a little bit more stable because now it's neutral. And so after this, we get a butane still with arm ethyl groups, and the hard Children will actually go right here. And the reason for that is because this carbon right here is now without it needed bonds, and it forms a carbo cat on, so it has a positive charge right there, and the car broke out on you Want to be US. Day was possible, and it's the most stable when it has to subsidiary wince as here, then right here, where it would only have one sub situation. However, there is a possible rearrangement. And so rearrangement can happen on the Alfa Carbons or the carbons right next to the positive charge of the car row Catalon And this carbon has the chance to become a three substitute car broke out on. And how does that is? It can transfer one of these methods groups over to the car broke out on. And this will cause the car Bo Katan, to move from this carbon to this carving cause it's losing one of its bonds. So now that carbon is the deficient one, and so that methyl group moves over and we now form or a Lincoln myself a little bit more room. We now form this structure here. But the plus with the car broke out on here and our heart surgeon from our first step would be over here or excuse me, it would be on this carbon right here. Now that that is taking care of, we still have H 20 and this h 20 well actually attach to the cargo catalon so that carbon is no longer deficient. And from there we'll get what's subregional structure with our dimethyl groups, and then this. We'll have oxygen with two hundreds. And since the oxygen now has three bonds, it will be positively charged are. And so we're almost done and having our desired structure. And so what we can dio is to get rid of this positive charge on the hard gin is in a when forming a compound. There's only multiple water molecules in this, and so we'll have another hydrogen or water compound. And what happens is this water compound can actually just pick up this extra hydrogen and give this oxygen the electrons and form a stable product. So it's a little backwards. But if you just look this compound around, you will get this answer. And that is how you go from 33 time at the one beauty in 2 to 3 dimethyl too beautiful and an acid catalyzed hydration reaction.

Hydrate is an ionic compound that has, uh, some water trapped inside. The generic formula is the salt. So the typical ionic compound formula with a dot and then an ex H 20 the X represents the number of moles of water trapped inside per bowl of the salt and so to determine the procedure. Typically, you're gonna heat up the hydrate until all the water has been driven off, and then you'll find the mass of water that was removed. So you take the original mass of the hydrated salt minus, uh, the mass of what's left over after you heated it up, and that will give you the mass of water that was driven. You'll convert that massive water into moles, convert the mass of the dry salt into moles, assuming you know the molar mass of the dry salt, and then you're gonna simplify that ratio between salt in the water. So the experimental process is really pretty simple. Just involves having a known mass of the hydrated compound heating that up until all of the water is gone. The difference in the mass of that of those two things the beginning that before it was heated in the after it was heated is the mass of water, and you're gonna convert that master moles and you're gonna find the ratio and thereby the formula of the hydrate.

Hello room today will be doing problem nine point eighty. And this is one of the more challenging problems in the textbook. This question states that dehydration of our starting material with sulphuric acid result in this cycle Pantene as a minor product, a jaw, the stepwise mechanism to how you would form this Al Kane and be draw other Al Kane's formed in his dehydration. At least one five member ring must be formed. So on this page, I'll show you guys step by mechanism how to form our mind of products and on the next page will form the other Al Kane's office. Dehydration. So we have an alcohol gave a strong acid just like before. We need to show that we will probe Nate our alcohol. And remember, I like using a tch plus and an A minus. So the oxygen of alcohol being with Philip will pick up that proton forming a sax ony um, compound here positive on positive oxygen, which is not favorable, not stable socks. So this water will just pop off to form neutral water and formed stabilized tertiary carbon kata just like before and other problems. But now we have a tertiary Carbon Canyon. And we need to make this cycle explain into a cycle vaccine. So how do we do that? So, on paper, Karl Okada chemistry is very beautiful. But in reality, car mechanic chemistry can be very messy. And, yes, you will have obviously majority of other products being formed, But you will have a lot of side reactions at the same time. So one of these minor products which will occur and honestly a very, very race, small fraction and smaller currents and probability. But the's products can still form. So remember, you're Sigma Bonds. All your signal bonds are formed from two electrons. And when we do nuclear feel like attacks, we do nuclear Philly attacks from two elections. So, in essence, is Sigma Bond. Sometimes Khun act as your nuclear far. So let me show you what I mean by that. So let's take this single bond right here. If I want to use those two electrons to nuclear physically, attack this caramel caddy on to neutralize it out form now cycle printing structure with the caramel cod. I'm being shifted up here. So now this is great because now we get our cycle pen tain, but we don't get our cycle. Pantin. If I kept my caramel cod and up here, I would only get Di substituted Dehydration products. That's what we want. So if I were to use these beta protons here in blue off these beta carbons, we would get Dyson's to the Elkins and not this minor product that the textbook is asking us for. So what I can do is yes. We have a tertiary carver, Katia, but we can do in our shift carve a cat and rearrangement one to shift using this method. So this metal group shifts over here. Then once again, we will get and tertiary car broke down. But now it's going to be within the cycle painting now the highlight, the better carbons. They're all equivalent because there's internal playing seventy of this molecule. So is that a car also doesn't matter which beta carbon, our contract based takes doesn't matter because they're all equivalent. But if our A minus, R H s o four minus picks up this proton and you make a new bond reformer ass a catalyst. But when you make a bomb, you to break a bond, so that seem upon will break forming our king and neutralizing our Carvel cada making four bonds too satisfied Architectural. This is how we formed this structure and our I said Catalyst. But once again, this little cur with minimal, minimal minimal frequency Minimal probability. More likely though, the other outcome. So this was a So let now let's go. To be more lately is obviously using our cycle. Heck, sane here with this car. Macadam here is already tertiary. It's already stable and we have beer carbons coming off this Carbon rifles Beta carbon right here. Sorry. Minus can easily deep in it. That too Forman Al came here to give us this other alkaline product, which is try substitute out came. But now the textbook says one of these products must have B five member. So I was go from this intermediate the covered cart and being up there. And like I said, the's Carmen's also have beta carbon date of protons because they're bigger carbons. They have better protons on dis a minus can actually d Probably one of these two former di substituted came remember. It doesn't actually matter which one it chooses because asymmetric molecules internal plane a cemetery bending is a Carl. So, as you see here, I gave you guys step by step synthesis of how to generate this minor product, showing the question plus two other AL kings that can be formed for Part B.


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