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Problem 3 (18 points). Anticoagulants have been in the news lately. The following is an analog ofa commonly deployed blood thinner used in the clinic Your task is t...

Question

Problem 3 (18 points). Anticoagulants have been in the news lately. The following is an analog ofa commonly deployed blood thinner used in the clinic Your task is to synthesize it using salicylic acid (a common acne medication) as the starting material: You must show the product of each step You do not need to state the number of equivalents of 3 rcagent for transformatlon: you need to Invoke an acid, please include an actual acid, not H-Aor Hiot Ifvou use an organometallic reagent as carbon so

Problem 3 (18 points). Anticoagulants have been in the news lately. The following is an analog ofa commonly deployed blood thinner used in the clinic Your task is to synthesize it using salicylic acid (a common acne medication) as the starting material: You must show the product of each step You do not need to state the number of equivalents of 3 rcagent for transformatlon: you need to Invoke an acid, please include an actual acid, not H-Aor Hiot Ifvou use an organometallic reagent as carbon source Ile. Grignard, Wittig; Lithium enolates), then vou must show the preparatlon of that organometallic reagent (one step sufficlent): Thls Is challenging retrosynthesls show us what you knowl Yout Taak: Hint: (uait onu rulitnoue througt Intereredinfot Spontanoour



Answers

(a) Write a reaction involving a lithium enolate for introduction of the methyl group. in the following compound (an intermediate in a synthesis by E.J. Corey of cafestol, an anti-inflammatory agent found in coffee beans): CAN'T COPY THE FIGURE (b) Dienolates can be formed from $\beta$ -keto esters using two equivalents of LDA. The dienolate can then be alkylated selectively at the more basic of the two enolate carbons. Write a reaction for synthesis of the following compound using a dienolate and the appropriate alkyl halide: (b) Dienolates can be formed from $\beta$ -keto esters using two equivalents of LDA. The dienolate can then be alkylated selectively at the more basic of the two enolate carbons. Write a reaction for synthesis of the following compound using a dienolate and the appropriate alkyl halide:

So here we're taking a look at some alky in an alkaline based content. And so the index of the hydrogen deficiency of A, B and C is to yeah, So this results suggest that we have a triple bond present or two double bonds, a double bond in a range or two rings. So a, B and C can all d colorize, so that suggests that they will have carbon carbon, multiple bonds. So a needs to be a terminal al kind. So this is confirmed by an oxidation experiment where we have the following structure ch three three Well advised to CH twos or by a carbon. What did I c h? So the hydrogenation of Beato hex ain shows that the chain is, um, branched. So, therefore be is three hacks on which looks as follows. Then the oxidation of C tells us that it's cyclo vaccine, which has the following structure

Hello, everyone. Today you will be doing problem. Nine point thirty six. And this problem gives us a ball unstick model of compound, eh? Which we will label here compound, eh? And ask us for several things. So the first thing I asked us is to determine the AIPAC name for this molecule, including the aren't as designation for any sterile genic centers. So if you convert that ball unstick model into a skeletal structure, as I've done here, we see that we have a cycle plantain with hydroxide, alcohol group, functional group, and right adjacent beta. To that, we have an isopropyl group. So the first thing that we need to do is identify a parent. Shane. The pain chain here would be the cycle plantain. And once we have identified the parent, Shane, what we need do is identify all the functional group. So we have two functional groups. As I mentioned before, we have one hydroxide and on carbon too. We have This is a ll pro pool group, um, attached to a natural carbon. So we actually have one, two, three, four. So that will be beautiful. But because we have that is so shape, it actually becomes an isil. Beautiful group here and now. In order to complete the name, we need to determine whether all the Kairos centers are either are Estero chemistry. Sofia Identifier. If you remember, recall what is Cairo center is a Carl Center is any carbon center that has four unique substitutions on it. So all the Carl, all the carbon centers on the cycle plantain except carbon one and two they both They all have two hydrogen atoms. So because of this, they're not four unique substitutes and therefore, these air a carl center yours. However, on carbon one into there is indeed four units of city. And so these are Carl Center. So if you remember determining RS rotation around the cow centers are his rotation clockwise as his rotation counterclockwise. And the rotation is specified by the atomic number of the substitute. So obviously, if you start with carbon number one, we see that there's an oxygen bounced carbon one. There's also a carbon and other carbons. Obviously, oxygen wins in terms ofthe ranking. Next, you need determined rank number two. So from those two carbons, which is a tie, we see that this carbon up here is bound to more carbons while this carbon down here's only bound tto. One more carbon. So obviously something that's bound to two carbons has higher priority than something about two carbons. Then one carbon. Sorry. So that leaves us three here. And obviously the proton that's going into the pages rank for, So I want to connect these dots. One, two, three. I will see that this is going clockwise. So I know that a number one it is our rectus rotation and they're using that same logic for carbon number two. We will identify if it is r s so attached to Carl Center too. We have one carbon, one carbon at one carbon. So that's a three way tie. It's not going to see what's attached to those carbon. So on top, we have one more carbon on the right side. We have one more carbon as well. However, on the bottom we have one carbon and one oxygen, so oxygen has a higher atomic number than carbon. So we know that this our group down here, we'LL get ranked number one leaving us with another tie that we need to break so this carbon is bound to two more carbons while this carbon is only bound tto one more carbon. So those two carbons wind that leaves us three or hear Survivor to connect those dots One, two, three with the lowest ranking hydrogen being within the plane of the page we see that this is also going clockwise So we also to get in our rotation for this carnal center So both carbon one in carbon to have our rotations. So if you remember from naming the easiest thing for naming is to start with the parent chain. So I will rides here all right here the parent chain which is our cyclo plantain. And now we need to add the substitute wants what we have attached to it. Well, we have a carbon one hydroxide group so we have one Psychlo pent. But then the Suffolk's for hijack said is all. So we have one cycle Pantanal, but we also have a carbon to an isil beautiful group. So we have a two isil beautiful one cycle plantain but we need specify the r and as stare chemistry. So it is actually one r to our this well, two is a beautiful one cycle pension All So that is our are you pack naming for this structure with the r est air chemistry identified. And now B is asks us to classify molecule A as either having a primary secondary or tertiary alcohol. We only have one alcohol here, so obviously we can see that this alcohol is bound to a carbon that has two unique substitutes that are non hydrogen sze. So obviously this is a secondary alcohol. The letter C asked us to draw a stare. I simmer for a and give its AIPAC name. So remember a stereo I simmer differs from a constitutionalism were a stereo. I simmer has the same molecular formula and same bonding as another structure. However, they differ in three D space. So if you can see here that the hydroxide and this is a beautiful is coming out of the page. So the stereo I summer is something that will be going into the page. So same Michael formless, same bonding. However, they differ in three D space so I can draw out one of those sterilize mer's right here. So and remember, by changing the position of any two substitutes around a carbon, you invert it, stare chemistry. So since the original molecule had hydroxide coming out of the page and that was our rotation and this stare, I simmer, the hydroxide now is going within the page. So right now, without even determining it, I know that the bottom carbon one is going to be s stay or chemistry or the top one remains the same. So it's going to be our syrah chemistry and this would have exact same name. Except instead of being one r to our it will be now one s to r two is a beautiful one. Cyclo pension. All now D asks us to draw a constitutionalism were with the hydroxide group and give it all you pack name. So a constitutional isom er is a nice summer that has the same molecular formula, but they differ in bonding, so you can be creative with this. So you need to have make sure you have the same number of carbon, same number of oxygen's and same number of hydrogen, but they're bonding will differ, so you can have many options of how he would charge this. I'm going to draw one of these arbitrarily, so if you see here the number of carbons remains the same number of agents. Smears remains the same. Everything remains the same. The only thing that differs now is they're bonding. So if I would give this name, I would need to identify the longest chain, the parent chain. And this case is actually kind of unique, because this case, the parents chain is actually going to be are straight Shane here, the longest straight chain we have. So he could either think of it as what I highlighted in red. Or you can think of it as green. What I'm going to highlight in green what you see here at these air, both three carbons, regardless of how you do it, and the constituents will remain the same girl. So how you want to draw this? So if I were to follow what I have in red, we see that on carbon one. We have a hydroxide group right here. Carbon two. We have a method all functional group and carbon three. We have this cycle of pain, Tane. So if I were to give this the molecular formula, if you guys recall how we do it so I was like starting with parent chain. So the parent chain is a propane because it's three carbons long. But now we see a carbon one of the propane. There's a alcohol. So it's one crow penhaul. And you see, I like building it from the end. And then a carbon number two. We have a method. So to Mme Ethel. And finally, Carbon Three, we have this Psychlo pencil group. This gives us our Are you packing aiming for this constitutionalism? Er next for question e. We also the drug constitution. I simmer, but now within either not with an alcohol I mean give its AIPAC name. So if you remember and neither is anything that has on our group so I can try this out in our group Oxygen another our group. So that's what I'm. Neither is so once again, you can use your imagination. There's endless possibilities. But I will destroy one arbitrary possibility here. And for this case, When you see when you're trying to identify the parent chain, you see that the most significant substitute here is actually the cycle plantain. Ah, unlike this one that we actually had three substitutes off this purple group here. You see that there's only one substitute off this pope. A group with this either incorporated here. So how we would do this is we would identify that. OK, we have a cycle plantain and attaching a cycle plantain. We have four carbons which you remember That's a s a beautiful, but then we have an oxygen combined to this for carbon. So if you remember something that we call a meth Oxy group so you can actually call this an ISA beautiful Oxy group. So same idea. And this actually reduces the name length substantially by naming like this. So this is why it's named as the parenting being the cycle painting Sophie, right? The parents chained like I liked doing and we identify all the substitutes. So like I said before we have this is a beautiful, but there's an auction right next to it. So it's a S o beautiful Oxy group. I saw your oxy group, so we just have an isil beauty Oxy cycle plantain. And now, finally, for F, it asks us to use the reactor aid original reacting that we drew from bones stick model and reacted with these following re agent so sodium hydride. If you guys were following my previous videos, you guys will recall that sodium hydride will associate into an A plus which instructed Ion and H minus being the hydride. The hydride is kind of you can imagine it as a proton mop. It is highly nuclear filic and it just Dipoto. Nate's anything with a label proton. So if we look at our molecule a label, Proton means a proton that is susceptible to be taken away, depending on the Ph or depending on the chemistry, that's your you introduced to it. So with his highly negative hydrogen, we see that the hydrogen off this alcohol can be easily depot donated to yield our depot native product, which would be this giving us a formal, negatively charged oxygen. And now moving on forward, we can use this negatively charged option as the nuclear fall for further chemical reactions. If it's introduced to an electoral file, next is asking if he what happens if we react this original re agent with a strong acid such as sulfuric acid so sulphuric acid. I like just to substitute it as h ey for any General ah, strong acid. So if you recall When you react something with a secondary alcohol to a strong acid, we actually get a dehydration. So dehydration means from S P three carbons. We reduce it down to Sorry, we oxidize it to S p to carbon, so we lose a degree of saturation. So what that means is that we go from an Al Kane to annul King, we gain a double bond. So we see here the nuclear filic oxygen, with its elections, can pick up that proton Proton ating itself to give us our pro nated intermediate. And I just I won't draw the steel chemistry just for ah sake of space. We have a pro Nate Intermediate. And now we see that Ah, we will form multiple products. The major product being the most substituted. So the most absurd Al Kane followings items rule would be when d pronation occurs at this carbon picking up this proton, making a new signal bond. When you make a bond, you have to break a bond. So we get bon formation here. So you get a bon formacion right there. Plus, we get water that left and remember this a minus is picking up the proton making bond when you make a bond to break a bond. So the signal bond between the carbon hydrogen breaks forming the Al Cain. But that means that we also the kickoff water. So there's no five bonded carbons on the small cubes. That's not possible. And obviously we reform our H A, which in this case is sulphuric acid. So because we're reforming our re agent, this's will be calling acid catalyzed mechanism and reaction because our catalyst is reformed at the end of our reaction. So you can do this dehydration with multiple things being used, strong acids or similarly, you can use particle and purity. Purity is our proton mops, so that picks up your protons to neutralize everything and make sure everything has no charges on particle acts as, ah good electro file at this on phosphorus center here. So you will get your same dehydration products with the most substituted being. This try substituted Al Cain following Zeit F stroll so this would yield the same product. Now if your two reacted with HCL once again, we would use HCL the strong acids without deep probe made in solution to each plus and seal minus and we need to identify what our nuclear file is here. So obviously our nickel fall is something that is electron rich and able to nuclear physically attack using its loan parallel actions. So we see that option with its tool, unparalleled transit will use one of these lone parallel Theron's to neutral nuclear physically attack and be appropriated by the's this proton and we see that we now have ponied water which is highly unstable. So water was spontaneously fall off, giving us a secondary carve okada and intermediate destabilized by inductive stabilization and neutral water. And because we're actually making a carb academy intermediate and the leading group leaves first, we know that this is going through an S and one mechanism as opposed to an S and two mechanism. Also, because it's a secondary I'LL call this also suggest that is going to be an Essene. One mechanism now is Claudia and I alone can attack with equal probability from both the top and bottom face off this plainer carbo cat an intermediate because if you recall karma Catalans rsp two carbons. So there plainer. So a fifty fifty chance this chlorine can either attack from the top or from the bottom. So you will get a receipt, Mick Mixture, that being fifty fifty aren't as an anti mers when chlorine attacks from either the top or bottom. And you can actually represent that all in one structure by drawing a squiggly line. So it shows you your receipt, Mick mixture. Sokal. So if you react, your starting material was Sokal. You will get the same products, but it's kind of through a different mechanism. So if I were to open a new page and we use AKEL So if you see here, that circle looks like this and we are also using the base purity. That's a nitrogen right there. So if I were to re jaw my molecule and I'm just not going to draw the steel chemistry just for I shall just drawing right here, it's enough space here. So obviously we need identify the nickel for electro file. Here. We see that the most electron rich Adam, is this auction from the out color being using and very election deficient. Adam is the sulfur right here which is being electron withdrawn from these election negative coins and this ah little bonded option here to receive that option. Will nuclear physically attack the sulfur Adam, causing this carbono group to pop up making formal negative oxygen, in which point that will re form your double bon and kickoff clients. Remember, every time you make a bond, you have to break a bond. Now that the bonds broken, this negative oxygen is going back down to reform your carbon old group with that extra loan para lecture on making a bomb. Because we made a bond, we have to break the bond. The bond that breaks is something with a good leaving group, which is this chlorine atom right here. It's not my job, our intermediate. And then obviously we have a chloride ion. But now we have a positively charged auction which is not favorable. Auction likes being neutral or negatively charge. So period in with this nitrogen having alone para lecture on this can actually nuclear physically pick up this proton and neutralized our oxygen so period and you can think of it as a proton mop and mops off any protons that caused positive charges on Adams and it increases the stability and drives. The reaction forward promotes completion of your reaction So now all we have done here is that we have taken this hydroxide, which is a very bad leading group on. We've created into something that is a very good leaving hoop. Now what can happen is our client Ion. Can nuclear physically attack this carbon center which is bound now to a very good leaving group and kick our leaving group off? So if you recall because our nuclear follows attacking at the same time as our leading group is leaving, this is an s a sin to reaction mechanism. Therefore, we will have an inversion off stereo chemistry. So if our hydroxide was coming out on a plain of the page, that means that now chlorine is attacking from the opposite side. So will be attacking from within the pages of represented by dash lines to give this substitution product and finally, the last product. The last reaction is when you react the starting material with tosel chloride. So tosel chloride also makes your hydroxide a better leaving group which can then be used for reactions with other nuclear falls to create substitution products. So similarly, you're hydroxide will attack your electro negative. You're sorry? You're electron poor sulfur Adam, causing the cardinal oxygen to break and giving this loan pair extra loan pair electrons to the auction nucleus making formal oxygen. Now auction having three loan parallel. Chuan's will use one of those alone pairs to reform the cardinal group making a new bomb because we made a bond. Now we have to break a bond and the bond that we can break here, obviously the most. The best leaving group here we can identify as being one of the hey lines, which is thiss chlorine ion. So that will break. And similarly, our intermediate would have a positively charged auction, Adam So that is why when used tosel chloride, we also use purity to mop up that proton. So now you have old Haslet. Now this oh tossed like Khun B reacted with further nuclear falls to allow us into substitution a box. But if you recall here at this current point there is no inversion off sterile chemistry that original Cyril chemistry is retained because there is no s into reaction. However, if you were to continue this with any nuclear fall, then it would attack from one eighty degrees the backside attack causing an inversion of stairs chemistry

Whereas to use green yard regions to create the following compounds. So we're starting with methanol to the A L D. In and positive in our hood. No, methane is one. So one carbon rescues bring my butane. So in order to get a green nerve agent, we're gonna react this with magnesium, ever other th f or ether. And we're going to get doodle Magnesium Bernard. So the magnesium is much less lecture negative in the carbon, so it's gonna have a partial positive charge. Therefore, the carbon is unequivocal. This is a strong base. And now we can react that with the out ahead. So it attacks the carbon carbon and converts the key to an alcohol. Let's hear this. And then you just add whatever was attached to Maggie's Amber mod, which was the four carbon chain. 1234 So if we count it, we have 12345 sweet Penhall. Oops. That's the first one Dependable. The second one is to create to external. Yeah, so let's start with. Start with this. And yeah, in order to, um, use the graveyard of reagent, we need a key tune and you get a key to any alcohol. So let's use the hydration reaction of al keens to get and alcohol static ethanol. Let's practice with a mod oxidizing agent because you have a primary alcohol you can use PCC or desk Martin appeared in. So again, if we react this with a strong oxidizing agent like lithium, aluminum hydride or sodium cram it, we're in it a carb oxalic acid. And we can't use carb oxalic acids with green yard regions. So even our herd And now I already showed how to create the green card region. So let's just react us with. We need four more carbons for external. I'll see his arm. She's magnesium chloride. This time it's the same process the carbon tax, carbon, carbon Q two and alcohol. So if the structure 1234 So we have or this is a stage three down there. 2123456 city to external. Yeah, next one is to create two methods to external, and the only thing you need to do here is replace the hydrogen with a metal. So instead of the instead of the starting material being to carbon changes, he is perp in, so use propane instead of to get to metal two. Excellent. Yeah. So the reaction between chloral benzine and proponent that's D so we can get chloral benzine from the Friedel crafts calculation. Reaction with permanent zipper pain is three the urn and positive ketone. And we're gonna have a key to non carbon tube. Because if we're if we're on carbon one or three had been out a hood. Yeah, and so to get the grand total to react chloral benzine with yes, get magnesium mover and the third or th f. Now you can react it with the cartoon. Alex. Yeah. So we have benzo, magnesium chloride. This attacks here that if we redraw it, we have this. It also looks like this carbon to is alcohol. And, um Ethel So what other way could could we create this product we could also use? Um yeah, we could have a key. Turn on. I'll say this. Yeah, And react this with metal. Magnesium bromide again? No, the same reaction. So we had he's had an alcohol and add the metal. That's another way of creating it. So the last one is creating to Hampton one all. Yeah, sorry. Um, the first one is fo magnesium bromide with one hex on. Okay, so M g p r plus x sign. And remember, there was a hydrogen here. And green yard reagents are strong bases so mhm it can actually grab it can actually react with all kinds. And mm hmm. Crop of hydrogen. But it's gonna look different. So we're gonna have this. Didn't really attack any carbon. So we still have this, and we're going to have ideas in Burma and plus methane. Remember the Ha Jin when it was actually? I think so. C two, age six. And we also have a This would be a negative charge on this carbon later on this one. Okay, so regrets create to help tin one or five room there. So let's react. Helped in with methylene magnesium brie mode to get the structure and then to have a negative charge here. We can react this with, uh, formaldehyde. I'm pretty sure be as weird to have a seven carbon June, and we need a primary alcohol. So we can't have any carbons where the hydrogen czar otherwise would have a, um, secondary alcohol. So if this reacts, we're going to get the structure if I can. And then 123456 Mm hmm. Seven. Um So if we draw, we have 12 than ever. Here. 21 Oh, sorry. Let's start at the wrong wrong starting compound. This should be should be hack sign, because we How many carbons? Okay, this gives us heck cell magnesium brew mode. So 123456 And it should give us the structure. Say, yeah, yes. So we have 12345 67 Alcohol. Here. They're 12 That's fine.

So we were taking a look at retro synthetic reactions are essentially given a target molecule and we're just having to like backwards. So we take a look at our first structure, my gosh, and that it can't draw actual synthesis. Arrow on. Now we draw our components where we have two missile Prepon, One island Bremer bending so sort of re agents that we're gonna be needing here is we're gonna be needing MGI andi e t 20 for this conversion to get to Phanom, magnesium bromide, new P, C, C and C H two c l to to get from our alcohol to our alga hide. Then we react these two together in the presence of e. T 20 on h 30 plus a Proton source than in the second step. We have PCC and ch two c l two. So in the next example we have we're making to synthetic cuts. It's moving straight onto our next example just to save a lot of time here. We've already discussed the sort of re agents that we need for these types of chemical reactions. So all we're going to be focusing on is the structures themselves to make us. And that's a cut green yard region on. This is generated using a alcohol starting material. Andi was a starting material. Also contains an alcohol. So I just chemically transforming our starting target molecule that we have into a primary alcohol. Because we can't achieve this chemical transformation here in Rabat to make a make or chemical cook. Now we can think about drawing are starting materials by one of our starting materials is in a box side. You just insult in a page and then on to our next example here in first of a chemical transformation into an alcoholic and we make our synthetic cut. Now we'll draw our materials ended up oxide. Well, we've seen this step before. We go from magnesium burn mind to just a bromide containing molecule. And then we used the alcohol form. Next example make a synthetic. It draws retros. And this is our Oh, and now we start to look at starting materials that we could use and this chemical transformation. So we know that we have to work backwards. So we start with our alcohol containing structure, convert this to grow me and containing structure that we combined to our green yard with the other material. We start with our alcohol containing structure and then we convert to Akita. So we have the next reality. Firstly, the chemical transformation from our key tone Thio alcohol We don't make a synthetic cup Another retros. And this is Sarah. Now we have our starting materials, but we need to work backwards for me. So of course we go via remain containing compound and then the alcohol containing compound. So this whole group was replaced with an alcohol group. In this the material that we have we are working with a primary alcohol final example. I believe we have a molecule that contains a foreman atom. It contains our benzene ring. So the first thing we do we draw our structure with appropriate functional group make us and data card here we're making to on our hydrocarbon chains. Well, as always, we go via berman containing molecule on any alcohol containing molecule


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Please explain these thoroughly. A solution containing a weak acid (pK = 7.5) and its conjugate base at pH of 8.5 has a good capacity to buffer the addition of ______. A phosphate buffer solution at pH = pK1 = 2.15 would have equal amounts of phosphate in the ______ form and the H2PO4– form....
2 answers
13 a) Is the set of n X n matrices with det A = 1 a subspace of Mnn? b) Is the set of n X n matrices with det A = 0 a subspace of Mnn 2 In both a) and b) write the corresponding sets by using set notation _ (You need to either prove O give a counterexample:)
13 a) Is the set of n X n matrices with det A = 1 a subspace of Mnn? b) Is the set of n X n matrices with det A = 0 a subspace of Mnn 2 In both a) and b) write the corresponding sets by using set notation _ (You need to either prove O give a counterexample:)...
5 answers
HakJara BuusLel nuL Lxl_4l Is MSHLiUAA Wltels Ll CE LA hl6ULetnSelcAALALAL 3ZEaAJdcs44sHeco~4}
HakJara Buus Lel nuL Lxl_4l Is MSHLiUAA Wltels Ll CE L A hl 6U Le tn SelcAA LALAL 3Z EaA Jdcs44s Heco ~4}...
5 answers
017 Product 1 PointWhat is the major product of the following reaction? (l.e, what is 2)N1zCi27ZHzSOa HzoCOzH COzHCOzHCOzH COzh Hoz"KOzCCOzhHOzCCOzH
017 Product 1 Point What is the major product of the following reaction? (l.e, what is 2) N1zCi27 Z HzSOa Hzo COzH COzH COzH COzH COzh Hoz" KOzC COzh HOzC COzH...

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