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Propose syntheses for each of the following molecules starting from methylcyclohexane as the ONLY source of carbon atoms in the products_ You may use compounds synt...

Question

Propose syntheses for each of the following molecules starting from methylcyclohexane as the ONLY source of carbon atoms in the products_ You may use compounds synthesized in any parts of this question, as starting materials for the other molecules in this question You may also use any other readily available reagents and solvents as needed.3_(e) HQ(b(a)OHOHOH

Propose syntheses for each of the following molecules starting from methylcyclohexane as the ONLY source of carbon atoms in the products_ You may use compounds synthesized in any parts of this question, as starting materials for the other molecules in this question You may also use any other readily available reagents and solvents as needed. 3_ (e) HQ (b (a) OH OH OH



Answers

Devise a synthesis of each compound from $CH_3CH_2OH$ as the only organic starting material: (a) $CH_3CH_2C$= $CCH_2CH_2OH$; (b) $CH_3CH_2C$ = $CCH_2CH_20CH_2CH3$. You may use any other needed reagents.

This is how to make different products using cycle plantain. So I'm going to start. We have cycle plantain. It just looks like this. A Pentagon. And I'm going to create koro cycle plantain, which is just a Korean on top. My cycle painting so well, we can see that we're just adding the halogen to my cycle pension. This is cycle Penton right here. Cycle Penton is an al cane. Al canes are generally un reactive unless we halogen ate it. So the best way to do that is just using steel to H g H V is light and then using that were already at the product. Okay, party heartbeat. I start with a cycle Penton and I want to end up with a metals equipment. So before even starting this problem, I see that I'm adding this carbon right here. One of the ways we can add carbons is using Bernard regions. So I should be thinking I want to use a grenade region eventually. So we haven't l. King. We know that al canes are generally on reactive unless we halogen ate it. So I'm going to use the or two it be. That makes me have a promo cycle. Penton like that. So we have a Bronco cycle contain and we know that we want to make a greener. So I'm going to use MGI either if there is just to check for example and that will make me have a greener. Okay, so MGB are we know that that is nuclear Filic. We want to attack something Electro Filic. So we want to add a metal group. So he was in a mess into reaction. We can attack ch three. I id ID will leave is a leading group and we will have our cyclo metal cycle Plantain. Okay, Next up, Percy, here we have cycle contain. We want to create this compound right here. We're having talking, and then I broke me. Okay, So same thing Al Keynes. Generally interactive. Unless we use religion ation or just you see, L t h three that will make me have my core up cycle maintain next up I want to make and how Keen. So we know that we can create Al kings from elimination reactions. So, using a strong non nuclear filic base such as l B A, I can make my okay. Okay, And then I see that I want to keep my keep my alky in place. But I want to add a roaming in this position. This position right here is a Lilic to my okay, So I should associate that with and B s that keeps my al can replace and put a roaming on the Olympic position. Que party party. I have my cycle contain and I want to create and alcohol. Okay, So some things before generally unredacted cocaine director would be or to light, that makes me have a roaming on top of my cycle contain. And then there are many ways to do this. Actually, I can First Maconel Keen and then either using ox immigration deregulation or hide reparation. I can then create my alcohol. Or I could just straight away do a nest into reaction using an A h and specifically a cold environment. The reason I specified colon environment is because if it was considered pot, then I might get a mixture of the elimination product, which would be the Al Cane. So, in a cold environment, I would get more of my alcohol than I would of my Okay. Okay. Next up party. I have my cycle plantain, and I want to end up with this compound. Okay, so somewhere to this reaction right here. Party where I added Corbyn's. I'm doing the same thing here. I'm adding this many carbons to my group of five. Okay, so I want to create some type of Grenier to facilitate their that reaction. So seal too hp. And again, I'm just using Halogen Nation. I can either use BR to HV or a seal to HV doesn't really matter critics that problem. Okay, so I have puro psych Lapentti, and then I want to create my grenade region. You've seen MGI and some type of either. And then I will get my Drinkard Regent MGI CEO. So my grenade reagent is considered nuclear filic. I went to attack something electrical. Look, that has the corresponding number of carpets. So I will use a cycle plantain as attached to a leaving group such as I Okay, and that will get me my product. That will just occur via an s and two reaction breath. I have my cycle plantain, and I want to create a dying. Okay, so something is before just holiday nation. All used We are to to be HB again is light that will make me have a roaming And then I want to create an al Qaida I'm eventually make talking's. But in order to keep one, I'm going to make I myself have an elimination action. So I'm gonna use in non nuclear Filic strong base, I think LD a Another good one is turkey talk side, okay. And that will make me have this my cocaine and then I'm going to use NBS. NBS will just make me have a roaming in the 11th position like that. Last but not least, I want to make another l king. So I have my leaving group right here using a strong non nuclear Philip base such as are used. LD This time I should get my dying.

Well, everyone, today we're doing Chapter eleven from sixty and this form asks us to generate these two products and b using on Lee this starting materials organic story material in the process. So what we have is for you need to start with this one, two, three Oh, it's so insert this uncalled starting material and we need to somehow oxidizes to an Al Qaeda with edition ofthe carbon. So we can say that in our products A we want one, two, three, one, two, three We have one, two, three, four, five, six carbons. One, two, three, four, five, six I went to retros. Emphasize this from the starting material. So let's break it down to how we can go about generating something like this so we don't need to add some carbon. So right now we really have feeling of three carbons and meet at an extra three. So we know that if you were to break apart this serial line or this al kind, you have to break this apart. Then we could get something that has three carbons and then something that also asked three carbon. So this has me Josslyn asked. Three Carmen's with three card. So we have this al kind here with this acidic proton that Commie depot nated to make a car. And I'm that can act as a nuclear fall in this nuclear fall. Canela act attack Electro file Electra flick Alcohol. Hey, lied with three carbons and leaving group, for example Khun sake. Romy. So this is probably going to be the last step. So from this out kind, we were in a nuclear physically attack this alcohol ally to kick off our daylight being bombing to give our final product. There's going to be collapsed last step when we go into the correct direction. But now how could regenerate? Thes two components will upstream until has three carbons And each of these components also has three carbons. So let's start with the easier one. So how do we get at Hale? I'd specifically bro me or chlorine from an alcohol working backwards. We know that we get this three carbons from our starting material by using p or three. Remember If, for example, instead of roaming, it was chlorine than I to use Sokal associate all too s o c o three, sir. So now we know how to get this start material from our this intermediate from Mercer Motel using Keep your three. But how do we get this from this? So let's first oxidize this too. And al came so one level oxidation. So we know we can office eyes this by using some sort of strong acid when he issues a serial plus so that will do public this too. Put it in water, remember? And now this wants to leave. But in order to leave, you need to do two things. Well, this pro nated this component alcohol the pro nated to water by picking up a proton from Here's now we have each tuo so the congregate base of our acid catalysts. But I mean, we need to reform our acid catalyst. So this age to me, to pick up a proton so I could pick up this proton to reform atrial plus the same time form our elkins Now from an owl kings of gold to our kind. So you've done this before Previous example. So if we add diatonic Hey, lied. We know that we will get edition on either side that he lied And then if I add some sort of base to equipment of bass, Actually two an age to, for example, just like in previous example. So this is everything we've done already And previous examples Because I'm moving pretty fast So we make a new bond We make a bargain break upon making you part when you make a bond break upon Sorry Hey, light falls out and you're into this two times you'LL pick up this pro time now make a bond killed spro mean event, I guess one you made your final inter needed here to get to the step So overall it's right this nicely So overall we're disturbed This product we're not at acidic water toget Aki and Al King I'll Cameron a diatonic hale I to be your to seal to anything but the atomic to get transition across and then we're gonna have some sort of base. So I'll write the actual salty version of that this tyre I mean two equivalence so two equivalents to get now the story material. Now from here we need to react with this. But how do we get How do we get this product from this will we took That's starting material. I did PBR three to get I will hey, Light, which actually electrified. But how do we make this into a nickel farm? Well, meaning to be pro Nate. There's ascetic proton to make carbon on busy sorting hydride. And then next will add our electric fall. Now we get one, two, three apartment addition to get a Now let's get B So from the let's see b, we have this only drawn another page. So maybe we need Tio start from this and get somehow too. So they're just comic Cardin's. One, two, three Well, calls coming off this carpet, remember? Yeah, So this is a little bit more tricky. So how we can do this is so we know that we need to form an Al Qaeda so we never really know her forms. All kind of off the street, Three cardinal time. So let's break this out kind bon. So we really know how to form this. So we know how to form this through. Ah, this synthetic scheme till the step. So this is the X came from here to here. So we know how to former all time and then from our Al Qaeda what we need to admiral leads one, two, three more carbons. So from this three cartons home we could think is now this is broken up to this outline is you know how to form and then we need to add it to This was three carbons with the central alcoholic secondary alcohol. So how we formed this? Well, we know that we need to start from our starting material being this. So we also know that if if you want to change this priory on call to a second down called the easiest route that I can think of is to make this into an alkaline. You add the alcohol using our company coughs editions. So then you would get your carbon cat down on your central carbon. And then you get the alcohol new flashing Carver tada to get second alcohol. So from here, we know that we've already made an Al cane. So how do we make the Al came all from the very first step of the synthetic scheme? So he had each trio plus reforms Al Kane. And now the thing is, now, if I just add a secondary carbon, then how do I make this into a nuke to him. Teo electro file Because I know that I can Deep Throat Nate, my al kind to make it into a nickel Fouls to nuclear physically attack my luck to fall somewhere. But how do I make this into an electric fall? Well, if you remember, how do you make peacock side so fine words who have some sort of let me arbitrarily right there. So I have three carbons. So one, two, three I have my central alcohol and I won't either side ready, Jason fighting. Hey, lied. I know that I could have a poxy ring formation. So if you had a poxy for information and you have something like this and now you're nuclear fall will attack on the least. Eric Lee hindered side. So the least Certainly underside of side. More number Proton to this This I've had more number of protons so we know that this new profile, in essence, can't talk the selective fire making bond and popping that open. So this is essentially the luxury Father, Ministers, generals How whom generate this electro file from this? Well, we just will oxidize this too. And our king So from al came how Can it get this? Hail. I'd hydra Allied hydrant allied components here. Well, we know from previous examples. If I add my diatonic Hey, lied with water then I can have some sort of call addition to my most of student. Carmen being the middle with the hill I being I would hear Solis Joe How loud work. So you would get some sort of Mark Klebnikov's edition with the coining Added this lease certainly in inside. And they have secondary caramel cod I on which water can neutralize. They have something like this pro native water, But then you also seal minus, which can pick up one of these protons commercialize your water. And this is exactly what I needed here. And this can undergo Deep Throat Nation. So if I make this into a stronger nickel file to help drive this reaction forward so you sort of a hydra to make old minus I know that this reaction I drew up here we'LL go We'LL go to progression to completion Sorry to form now my Electra fall Now take this election file and added to my nuclear file here and get my final product So let's draw out all the steps neatly so we know. First, we need two components made this components and any this components we want. We need to. So we draw how we really went through how to get to so from the same material. This is how we get our left profile, but hard to get a nickel, Follow your dad and step part one. So now I just re draw everything from part one by redraw that then Now I haven't Electra fall. I'm reacted with my nickel fall, but I d protect this on need sodium hydride. So I'MA sew your headaches of depo name by nuclear fall. So, innit? Talk this and then remembers an attack on this carbon being the least air quit balky carbons was an attack on this carbon. So then I would have and oh minus, because I'm going to make a bomb you break upon. So then we get to electrons on option. But you need an alcohol. Send stuff to this. We need to add water to neutralize everything. I mean oh, minus being a wage. And that's exactly the product that we receive. And B

This is Theo. Answer to Chapter twelve. Problem number seventy four from the Smith Organic Chemistry textbook. We're asked to construct three molecules the stipulations for this problem or that every carbon in the molecules has to come from a molecule of ethanol on DH. So for a we start with ethanol we treated with P B R three to get bromide, then potassium turkey Talk side Teo, get a scene. The Sal Cain treat that with bro mean gas on DH. We'LL get to die bromide on DH. Then we can use to equivalent of sodium, eh? My ID to get to a settling on. And then from a settling it's it's pretty much exactly what we've seen before. In other problems treated. Settling with sodium hydride on dh then sorry and alcohol. Hail ID out of form New carbon carbon bonds. Of course, because of the stipulations of this problem, we have to use s old bromide on. We already showed on beginning of this problem the very first step How how this ethyl bromide can be made from ethanol. So we are allowed to use it on DH. Then we'll de protein ate the other side of the al kind at another molecule of ethyl bromide on that gives us all the carbons that we need. So we just treat that al kind with sodium metal and liquid ammonia into a dissolving metal reduction on DH. We get our target molecule for a on now, for B, we can build on our final intermediate from, eh? So we would do everything to get get back to this final intermediate that we used on. Then this time, instead of using sodium metal and ammonia, we would use hydrogen. Yes. And when Lars Catalyst, that will give us the sis l keen instead of the trains all Kane on. And we can treat that with M c p b a to get to this park side. That is our target product for B. And then first see, we can used the Cecil Keen that we made in B on DH. Then, rather than treating it with M c p b a treated with oz me, um, tetroxide on, then sodium by soul fight and water. Ah, and that will give us this target. Uh, dialled. Sorry. I'm tryingto move it over so it's a little easier to see. Didn't go. So, um yes, that will give us this this target. Dia ll, uh, for si on DH. So that is the answer to number seventy four.

This is the answer to Chapter 11. Problem number 59 fromthe Smith Organic chemistry textbook. And this problem says, devise a synthesis of the key tone three hex unknown from ethyl bromide as three only organic starting material s. So all the carbons in three hacks unknown have to come from ethyl bromide on. We can use any other re agents that we need. Okay, Uh, and so to start, I'm gonna taken ethyl bromide. Um, and I am going to do an elimination reaction with potassium turkey talks ard, and that is gonna get me to the AL Keen here. Okay, then. So from that Al Keen, uh, we can know ruminate So elemental, bro. Mean, that's going to give us the dye bromide. Okay, um and so now we have the dye bromide. We can treat that with two equivalents of sodium a mine, and that is gonna get us to the al kind. Um, and now that we are to the AL kind now we can start forming new carbon carbon bonds so we can t protein ate this out kind with strong base. So sodium high, Dr. Um and that will get us this satellite eye on. Ah, And if we, uh, used the satellite, I on with effort bromide, Since this is where all the carbons have to come from, Ah will get a displacement on dso we end up with that. Okay. Ah, And so we now have a four carbon chain. Um, and we can just just repeat what we just did. So, sodium hydride again eyes gonna de protein eight Uh, the al kind like this now and so again, another equivalent of ethyl bromide is going to give us our six carbon chain, which is exactly what we need. So six carbon chain. So all of our carbons Aaron Place. Ah, And now, um, since we're trying to make, uh, three hex unknown, um, and our al kind is between carbons three and four. Um, and this molecule, it's metric, so we don't really need any further control than that. And so we can ah, just use water. So fear Gassid and mercury, so feet. Ah, and that is gonna get us to our key tone. 123 56 Key tone on carbon three. Okay. And so that's it. Um, yeah. And so since since we were limited Thio, starting only from ethyl bromide. We just had to get from ethyl bromide to ah, settling. And then from settling, we could d protein ate that to make the satellite eye on Ah, and then use that with two equivalents of ethyl bromide sequentially to build our six carbon chain on. Then just install Archy Tone, and that's the answer to.


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