5

Draw all the missing electron-[ushing #rows that ona #uth I Indicaled tanslutons some C1SeS ou mav hnxz drx in mmnlicd hydrogens order Iu} corrertly show the anowsH...

Question

Draw all the missing electron-[ushing #rows that ona #uth I Indicaled tanslutons some C1SeS ou mav hnxz drx in mmnlicd hydrogens order Iu} corrertly show the anowsHz N4;Hci8the: molecule bclow electrophilic. AlkenCS un opically nucleorhilic but Lhe alkene ExplainShown below is & 3-stcp catoncuton rcarungcmcnt Draw intcrmediale carbocation and draw pushing arrows showing how thc slirting cation convcrtcd cach iniennediate theelectrn canon und how the interediate cations are convcried t0 the

Draw all the missing electron-[ushing #rows that ona #uth I Indicaled tanslutons some C1SeS ou mav hnxz drx in mmnlicd hydrogens order Iu} corrertly show the anows Hz N 4; Hci 8 the: molecule bclow electrophilic. AlkenCS un opically nucleorhilic but Lhe alkene Explain Shown below is & 3-stcp catoncuton rcarungcmcnt Draw intcrmediale carbocation and draw pushing arrows showing how thc slirting cation convcrtcd cach iniennediate theelectrn canon und how the interediate cations are convcried t0 the next intemediate and the final cuton 410



Answers

(a) Draw the product of the following [4 + 2] cycloaddition, which was carried out in the early stages of the synthesis of the alkaloid reserpine (Problem 22.91). Indicate the stereochemistry at any newly formed stereogenic centers. (b) Draw the p orbitals of the alkene and the terminal carbons of the conjugated diene, and show how the orientation of the reactants and orbital overlap lead to the observed stereochemistry.

This is problem 15 of Chapter 27 looking at Before, plus to Psychlo edition of this given reaction. Since this is a four plus to Psychlo addition, we know it will involve the or pie electrons of our dying, which we see here, and the two pi electrons of a dying A file. And we'll use one of the double bonds on the Benzo Quinn known. And it's a thermal four plus two psycho addition. Since it's run under Heat has indicated here, which means it is a deal's older reaction. Are dying is shown here in the S. Trans confirmation s refers to this single bond, and we could see the double bonds Airtran's to each other across the single bond. But for a deal's older reaction, the dying must be in the S cysts confirmation because then s trans dying would lead to a cycle heck scene with a trans double bond which is impossible to form. So let's redraw are dying in the S sis confirmation. And now we can draw our mechanism arrows to see what a product will look like for the answer to part a of this problem. And if we follow our arrows. Then we can draw our product and we see we formed a new six member ring, which is what we expect from a four plus to Psychlo edition. By forming this ring, we've also formed three new stereo centers, which I'll indicate here, here and here part. They also asks to indicate the stereo chemistry at these new stereo centers and to determine that, let's move on and look at part B part be asked us to draw the P orbital's of the bonds we used in this reaction. So let's draw this a little differently to try to visualize how the new bonds air being formed. So here's our Dana file, and here is our dying so we can imagine the dying is being introduced from Be low, the dining A file And now let's draw the P orbital's. On this diagram. You're the P orbital's for the data file and the pee or petals on the dying. A thermal Psychlo addition happens between the ground state homo of one of the reactors and the ground, ST Louis, Mo. Of the other reactive. Let's dry in the ground. ST Louis, Mo. Orbital's of the Diana file and the ground state Homo Orbital's of the dying. We could also consider the loom over the dying and the home of the Diana file. You could try that for yourself to see. The result will be the same so we can see the lobes of the dying and the Dana file match up perfectly, allowing the two new bonds to be formed. Since we're imagining the dying to come in from below, we can imagine that the hydrogen sze on the data file are being pushed up and out of the way. And similarly, the Esther on the Dying is being pushed down and out of the way of the newly forming bonds so we can now indicate the stereo chemistry of our new stereo centers. The two hydrogen sze were both pushed in the same direction. So there, sis to each other and we said they were being pointed out, are pushed up. So let's show them pointing up on our product. And we said the Esther was being pushed down. So let's show it pointing down on our product now. We could also consider the dying to be introduced from above Dana file, in which case we would draw the hydrogen is pointing down and the Esther pointing up. This would give us the same relative stereo chemistry, and in this case it would be the in Antium er of the product I've drawn here. You can prove this to yourself by building a model of the two products. This completes problem. 15 of Chapter 27 Her part A. We drew the product of the four plus to Psychlo Addition and indicated the new stereo chemistry. And for Part B, we drew the P Orbital's and explained how the orbital overlap led to the new stereo chemistry.

High in the problem from General Kane's and all kinds. We are given some of the structures of Elkins. We have to write the structural formulas for all the possible public assistance which are formed when each of these given elkin reacts with hydrochloric acid that is at seal. And also we have to label the carbon katanas primary sick in the auto Cherie. So first of all, let's understand what our primary secondary industry carbon gotten primary car button labeled as one degree is that carbon cotton with the carbon with positive charges bonded to only one carbon atom. While a secondary carbon button labeled as two degree. Is that where the carbon with positive charge is further bonded to two carbon atoms of L tile groups or maybe of a rebel group. Then a tertiary carbon button labeled as three degree. Is that where the carbon with positive judge is further bonded to three other carbon atoms. So now we will start with the first one, the first one is this one more thing in all these Elkins when they react with hydrochloric has said the positive charge is developed on the carbon atom which are double bonding. So the two possible car button in this case are shown here. Ch three, Ch two C. Wanted to Ch three and positive charges developed on this carbon atom. Then Ch two, Ch three. Another car begotten with this molecule possible is Ch three, Ch two, ch bonded to CH three, then Ch CH three and positive charges developed here. So these are the carbs proteins formed by the reaction of first Elkin with hydrochloric acid. So this carbon gettin where we have the carbon atom with positive charge. Wanted to three other carbon atoms is the shooting carbon get in this car back often with positive charge carbon atom bonded to two carbon atoms represents secondary carb Accutane. Then we have Next Elkin where the possible victims formed are shown here, CH three CH two ch having positive charge. The Ch two Ch 3. This represents carbon with positive charge bonded to two carbon atoms further so it represents secondary kabuki, italian. Another structure for carbon button possibly CH three CH two Ch two, C. H. With positive charge CH three here also the positively charged carbon atom is wanted to two of the carbon atoms. So it represents secondary car bucket in that is two degree car back it in. Then we have the third elkin where we have the structure. The two possible carbon kittens in this case formed are shown here, we have one of the carbon katan has the positive charge on the carbon atom to which al Qaeda group that is metal group is bonded this structure and in this case the carbon with positive charges bonded to three carbon atoms. So this represents three degree. That is tertiary car broke, italian another car market in structure with the same molecule possible is shown here where the positive charge will be on this cabinet um and this cabinet amid positive charges bonded to two other carbon atoms. So it represents two degrees that is secondary carb. Okay to in then we have the last molecule where the two possible carbon kittens with their types are shown here. This is the first carbon cotton. We have the positive charge will be developed on the carbon of this ring. And this represents carbon with positive child wanted to three carbon atoms. And so it is a three degree that is tertiary carbon cotton. The next car book written with the same molecule formed will have the structure as shown here we are. The positive judge is present on CH two part That is a turban of CH two bonded to this ring, so this represents a carbon with positive charge, wanted to only one carbon atom, so this represents primary car back in time. So these are the structures of possible Karbacher teams formed with their labeling as primary, secondary or tertiary car back in time.

Yeah, Just don't You hate it when a question like 48 has letters up Tio killers trying to get through this on fast. So he has metal methylene methylene, and then this all the hide. Great. And so it's asking us if we react this with multiple re agents. What? We're going to get first on the yacht hydroxide. Of course, that's going to make this carbon nuclear Filic. It's going to react with itself so we can generate 123123 this product right next. We have no h minus and formaldehyde. So this formaldehyde is goingto act as Thie Electra file. So will generate this compound for C first we're doing lt, eh? And then reacting with this Al the hide and then we have water. So of course, hell d is going to make our Alfa Carbon super nuclear Filic are going to introduce her Aldo hides who are actually going to end up with very similar products. But now we still have that metal group that's attached pretty sweet living on D. We are reacting way I said too Theo to PT too. That is this 13 di s there So I'll go ahead and re draw our ex starting material books. My screen doesn't really work that well off from that side. So try a little bit closer. This is going to be our nuclear file again. Gonna knock off one of the's? Oh, actually, I'm sorry. So if we're using sitting with oxide and ethanol, this is going to be the much more acidic Proton. So this carbon is definitely going to be the nuclear file to attack this one. So, under quiz this product, if we have acid, we could cleave off this whole group, but for only ending with ethanol. So this is our final product E career going to react This with meth, a lithium and then water. That's their product. Great. If we have sitting Bora hydride methanol, it's of course, that gets us to our primary alcohol. She we have hydrogen with palladium on carbon. This is also reductive conditions to get us to our primary alcohol for H, we have nicer glycol with tossed Ilic acid. Of course, this act as you're protecting group will generate this acid towel. I we have C h three and H two and mild acid, which is the pH around 4.5. So here we're going to have our mean The condensation they'll fall into our nitrogen was our stage three intact generates our I mean, also known as the shift base. And Jay, we have diamond full. I mean, so will generate the the mini. Um, but that's super unstable. Sze, Of course, this touch more ices to generate the in. I mean, that in portions stands for the Al Keen, of course. And then you have just You're mean. Okay, our doing We are on kay. So we're using 03 age to us before super oxidizing conditions is going to take our all the hide all the way up. Tio Carb. Oxalic acid. Yeah, it's like it l p r too. And we have this car. Looks like acid. Mm. We have this village for n sit in cyanide and it's still for Oh, we have lt, eh? What? It said three. I pretty sweet. Okay, so if we have L. D A. This is what our starting material is late. So of course, after a deeper to Nate, we can attack the nuclear file. I'm sorry, Eun Attack. Would this nuclear file to this electric Filic. Leslye died to generate this product for a judge who are actually forming our science a hydra in so that we have nuclear feel like cyanide attacking our album Hide and opening of and an age seal to protein ate that Wilcox side. Finally, with our vintage reaction, we're losing trifle phosgene oxide in this reaction and replacing it with Nick Harbin. So we end up with this entirely. Carbon hydrogen are hydrocarbon on Lee was no header, Adams.

All right, This is the answer to Chapter twelve. Number thirty eight, Fromthe Smith Organic chemistry Textbook on DSO. This question is asking us what would happen if we treated to Psychlo Pantene with twelve different sets of re agent conditions. Um and so what I've drawn is ah Drew cyclo Pantene at the top here. So this is the starting molecule for each of these. And then, ah, listen, the raging conditions and for the reactions or something occurs I've drawn whatever has changed in red to make it a little easier to see on DH Then for several of these, no reaction occurs on DH. So we'LL go through them one at a time and talk about each so for a ah, it's ah, hydrogenation with hydrogen gas and palladium on carbon. So we know that that's going to ad to Hodgins and replaced the double bond in the starting material. So that's what I've drawn here. Um, so for B and foresee there to other types of reductions, so be is hydrogen gas and Linda Lars Catalyst on then C is a sodium metal and ammonia liquid ammonia. So it's the dissolving metal reduction, and we know that they will dissolve a now kind to an AL keen selectively. But we should also know that neither of them will taken Al Ki ng further all the way down to a now Cain and so for be in for sea. There's no reaction. Um, so then d, uh is using Paris eating gassid and so it's an approximation and so we know that that will give us the pox side. That's what I've drawn here for day. I'm so hee ah is an approximation. So the first the first part of it is exactly the same as day. So you're after after one for you. Get the pox side on DH, then the second condition's condition too. You know, water and base. You're going to open that up, oxide, and it's going to give you ah di hydroxy elation. So you'LL have added two alcohols in place of the double bond on they will be anti to one another on So I've drawn that. Make sure that you do know you will get either configuration with these conditions So you'll get a fifty fifty mixture of peace too, s so then for f f is Ah ah Naz me um tetroxide sin. I hide your ox elation on DH so they're using and metal more Fellini and oxide, which is an m o here so that you can use just a catalytic amount of the Oz beom tetroxide and use the Stoke in metric amount of the an M o on DH. So that gives you a Sendai hydroxy elation. So unlike e, both these alcohols are on the same side in this molecule us moving on to G. It's a potassium permanganate. Die hard rocks, elation. So again we get the sin. Alcohol's there. So that's sort of drawn s. So then H would be trying to treat this Al keen with lithium aluminum hydride and then water. I mean, so that's actually not going to react at all. So lithium aluminum hydride is ah reducing Agent Andi, if we were to use it on something else as well see later in this problem, we would get a reaction. But when it's just a nalc een in a molecule with him, aluminum hydride is not actually going to do it. So no reaction for H s o I eyes a nose analysis eso ozone followed by treatment with dimethyl sulfide woman again. I always abbreviate dimethyl sulfide. GMs has I've done here on DH. So what you would get there is cleavage across the AL keen on dso you would actually get the ring toe open on DH. So instead of a cyclic molecule, you know, just have ah, five carbon chain without a hides on either end. Oh, and so that's I s So then, Jay, Um Isa Sharpless approximation. So remember, the sharpest conditions allow you to stereo selectively a pox, it eyes and a Lilic alcohol. Oh, are the arcane part of an electric alcohol. But it only works on Al Keane's that are part of a well like alcohol systems. And so, of course, in just regular cyclo Pantene, there's no like alcohol and therefore the Sharpless conditions don't work on Therefore, for part j ofhis problem, there is no reaction s So then k it'sjust an emcee pba up oxidation so sort of drawn here we would get thehe pox side treating this al ki ng with M c p a. On then l is asking us to do the emcee pba up oxidation on, then to treat that resulting product so remember. So for l after m c p. B A treatment. We have the answer from Cat. We have this product, the Parkside. So then we're going to treat that a pox side with with you. Move them hydride and then water. Ah! And the result of that would be what I've drawn here, which is announce a hole at one of the carbons that was formerly part of the Al Keen. Ah, and the other will get ah, hydrogen. And so that is the answer to Chapter twelve, number thirty eight.


Similar Solved Questions

5 answers
Civen that ul = projv " and u = ul+ul which cf the following is true?uL 1 uull |l "ull .u = 0Nene cf the cther eptions~ll 41 =0
Civen that ul = projv " and u = ul+ul which cf the following is true? uL 1 u ull |l " ull .u = 0 Nene cf the cther eptions ~ll 41 =0...
5 answers
Di . 7047123Onllly (RIZ AsshsstiencDue Sn 074d1{2018 1139Janze popularlon, 70 % afthe people have been vaccinated,KSpeople are randomly seleced, whac Is the prcbabllcy thac AT LEAST ONE of diem has been vaconaoed?alve vouanstdeomal (0o ac least 3 places)Waqjon_PreveytPoice porsbk Tna % JE2MO[ 1 01 1 Mumuralurttlinrqu- ErxmlZHLomie
Di . 7047123Onllly (RIZ Asshsstienc Due Sn 074d1{2018 1139 Janze popularlon, 70 % afthe people have been vaccinated,KSpeople are randomly seleced, whac Is the prcbabllcy thac AT LEAST ONE of diem has been vaconaoed? alve vouanst deomal (0o ac least 3 places) Waqjon_ Preveyt Poice porsbk Tna % JE2MO[...
5 answers
Heoty aPuint Dctermine the struciuneCtHtO3H(s)3H(s)3H(s) 2H(s)3h(t)ZHlq)
heoty aPuint Dctermine the struciune CtHtO 3H(s) 3H(s) 3H(s) 2H(s) 3h(t) ZHlq)...
3 answers
Pointi22ISt xaed tdA Wehe {Probjbuln iht =Fl} 0rm+ 514n 78 ' Ttt Danta}Khatuticd Jbntittd anycZfmn atn Elanks iaxe? Foled bidenal 'ual nt approdch empcrimgol Iollotrg - Kculturet icalense; 'pow) {574n0 [opele nlittet Mjc (nle mated Iccturng Luna Hmpl emok duld Shoxi 'Voli maik Partial ( credite u bes Ehen4
Pointi 22 ISt xaed td A Wehe {Probjbuln iht = Fl} 0rm+ 514n 78 ' Ttt Danta} Khat uticd Jbntittd anyc Zfmn atn Elanks iaxe? Foled bidenal 'ual nt approdch empcrimgol Iollotrg - Kculturet icalense; 'pow) {574n0 [opele nlittet Mjc (nle mated Iccturng Luna Hmpl emok duld Shoxi 'Voli...
5 answers
Find dy/dr by implicit diferentiation. You are required to show a least 3 sreps Failure ro show steps will result in zero_duld
Find dy/dr by implicit diferentiation. You are required to show a least 3 sreps Failure ro show steps will result in zero_ duld...
5 answers
Use the graph of the given quadric surface to answer the questions0.80.62 0.40.2(a) Specify the name of the quadric surface. (6) Write the equation of the quadric surface in standard form:
Use the graph of the given quadric surface to answer the questions 0.8 0.6 2 0.4 0.2 (a) Specify the name of the quadric surface. (6) Write the equation of the quadric surface in standard form:...
5 answers
You roll pair of ordinary fair dice repeaterlly: What is the probahility that three comes Ip before the first time before seven cOmes up. (Hint: Ignore all of the rolls which neither three nOT seven COmG #p So Wc (I think of this #S An exercise in (Onclitional probability: )
You roll pair of ordinary fair dice repeaterlly: What is the probahility that three comes Ip before the first time before seven cOmes up. (Hint: Ignore all of the rolls which neither three nOT seven COmG #p So Wc (I think of this #S An exercise in (Onclitional probability: )...
5 answers
In the figure two tiny conducting balls identical mass m and identical charge hang from nonconducting threads of length Assume that approximate equal, sin If L = 120 cm, m 11 g, and 7.0 cm, what is the magnitude of 9?so small that tan can be replaced by itsNumber000000041Units
In the figure two tiny conducting balls identical mass m and identical charge hang from nonconducting threads of length Assume that approximate equal, sin If L = 120 cm, m 11 g, and 7.0 cm, what is the magnitude of 9? so small that tan can be replaced by its Number 000000041 Units...
5 answers
Saying- 'The weather today cloudy, therefore, we must be in winter" iorm oi Detective reasoningInductive reasoning Experinental deslgn Deductive roasoning
Saying- 'The weather today cloudy, therefore, we must be in winter" iorm oi Detective reasoning Inductive reasoning Experinental deslgn Deductive roasoning...
5 answers
In(x91) dx VXThe integralconverges to 0converges to -364goes toconverges to 364goes to
In(x91) dx VX The integral converges to 0 converges to -364 goes to converges to 364 goes to...
5 answers
Use the unit circle to verify that the cosine and secant functions are even and that the sine, cosecant, tangent, and cotangent functions are odd.
Use the unit circle to verify that the cosine and secant functions are even and that the sine, cosecant, tangent, and cotangent functions are odd....
5 answers
Was Fonuilaally After 12 'daposited (present account that eams (onjea O thes into esaceounnt intcrest has grown (0 SLS SIS [ moneyFormula: L AAsume dhanoothly take What 8 25 your monthly year mortgage payment? for 5365 8 at an annual 1
was Fonuilaally After 12 'daposited (present account that eams (onjea O thes into esaceounnt intcrest has grown (0 SLS SIS [ money Formula: L AAsume dhanoothly take What 8 25 your monthly year mortgage payment? for 5365 8 at an annual 1...
5 answers
1. In addition to the features that are directly used fortransformation, the vector (pGEMt-easy) also includes oriC, anorigin of replication. Why is this feature useful for molecularcloning??
1. In addition to the features that are directly used for transformation, the vector (pGEMt-easy) also includes oriC, an origin of replication. Why is this feature useful for molecular cloning??...
5 answers
MISEED TKIS? Read Sochon 0 0 (Pagea 225 2201 Lana IME 6 0046c470nl Inont #hbie IuI: 915 Fample naata Maze 0/ 0 475 Rai pcotguim 740 mtn He and InnnatuneolntnPart APftnolcubrnheuteAd
MISEED TKIS? Read Sochon 0 0 (Pagea 225 2201 Lana IME 6 0 046c470nl Inont #hbie IuI: 915 Fample naata Maze 0/ 0 475 Rai pcotguim 740 mtn He and Innnatuneolntn Part A Pftnol cubrn heuteAd...
5 answers
F(x) = 0x C = 0fx) = SeSx 0 = 0
f(x) = 0x C = 0 fx) = SeSx 0 = 0...
5 answers
FalseConvert the point (~V3_ <0,in rectangular coordinates to polar coordinates that satisfiesSelect one: None of these(~v6 (~v6, (-v6,Tire
False Convert the point (~V3_ <0, in rectangular coordinates to polar coordinates that satisfies Select one: None of these (~v6 (~v6, (-v6, Tire...
5 answers
What prlce should the company charge to obtain the largest revenue? (Round your answer to the
What prlce should the company charge to obtain the largest revenue? (Round your answer to the...
5 answers
(10 marks) Find an equation of the tangent line to the curve of f(x) = xe +1 the point (1, I+e).
(10 marks) Find an equation of the tangent line to the curve of f(x) = xe +1 the point (1, I+e)....

-- 0.019919--