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Design a high-yield synthesis of each target starting from benzene. Noz ocksDrDu...

Question

Design a high-yield synthesis of each target starting from benzene. Noz ocksDrDu

Design a high-yield synthesis of each target starting from benzene. Noz ocks Dr Du



Answers

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

Starting from benzene, we can first functional eyes using a shin of three an age to us before to generate thiss nitro group on the benzene ring. Next, we can reduce this with hydrogen. Played him on carbon to generate an Elin. Next if we use an Anna too. And HCL, we can access this. Guys assault this size Assault can then be reacted with something like touch your beautiful ammonium fluoride which is really just a nuclear filic fluoride source to get one of Floro benzene a tte same time here. If we generate this 90 a group, if we use more fuming interna three an age to us before this meta directing withdrawing group can orient the electron IX of this molecule two nitrate on the meta position. Next, if we reduce sorry with the re agent of, say again played him on carbon hydrogen gas. We can access the dia mean, of course to equivalence of an ana too and hcl to access assault followed by age 20 and we can access this die alcohol on the fencing ring. Percy, we have to access this compound and any time that you have a north a substitution it's actually quite difficult to get because if you imagine we started up for this method group and then just tried toe I, Odin eight would actually get the ID Nation at this position here. So it's actually much better if this position was functional ized before, so that we could I Oh Jin hee at the very last step. So if this came from this compound, we could have gotten this from this molecule here. Of course, they could have gotten that from the simple call you in to thinking about this reaction forward. We can take her benzene and access with 40 equivalence chloroform in a ll steal three To get this mano a calculated product Next with nitric acid and sulfuric acid, we'll access the Paris substituted molecules from here. Ty, coordinate like news. Hi, Dean. And we may need a catalyst. Say they'll steal three. Or in this case, Rob's a lie. Three. And lastly, we need to get rid of this group. So we're going Tio, use an antenna to in HCL it's generates assault. And then finally was simple. Aged three to Pio, for we can generate the hydrogen on this position taxes their final compound. And for last molecule we need to generate. Try substituted Clara Benzene. Of course, this can come from again having the 90 group on this position. This comes from the single nitro position. So I challenge you actually too. Give the re agents of how we can go forward between these two sealed too. And iron. Try chloride in excess. We'll get you the tri chlorinated one. And we've already discussed how you can get Teo the free hydrogen. First, you'd have to use hey and two and they see l followed by your hydride source.

Hello, everyone. Today we're doing Chapter 18 pounds 32. In this form, acids synthesized each of these compounds starting from benzene. So it's kind of a retro synthetic analysis. We have these three products, and we needed formed these each of them from benzene ring solicitor with a the first one's from benzene Ring. We're adding one carbon and then were oxidizing that one carbon to a the highest oxidation level, which is a car bucks on the basset. So we we don't know how to add on a car. Books look acid directly yet we can use the Green Yard to reaction, but we haven't actually gone to that. And since this chapter is talking about reactions off aromatic compounds, we won't actually use Green Yard. So I think that's will be more steps than another post. I was introduced in this chapter, and that will be, for example, something like feel crafts calculation and followed by oxidation off that carbon to yield. Our car looks like acid, so we need to his first star from Arbenz in rain and count. How many Carmen's were adding well, really adding one carbon so we'll add that one carbon attached to a living group like chlorine and at our Lewis acid to it for fetal crafts calculation and then product of this obviously would be or edition products or yeah, actually, this is a substitution product being one method, all on any of these carbons inventing things are equivalent. Now we've added in all those carbons that we need to add S o. The next thing is we need to oxidizes carbon. Not just two now the height but fully oxidized. It's all the way to the car broke, sold acid step. So when you do is you need to add some sort of oxidizing agent. One of the examples that textbook use is camera four testing for my agonies. There's a very strong oxidizing agent. If you combine us a little bit of heat, you can fully confirmed that this is the carbon here. This extra sickle carbon or Ben's like Carmen is going to be fully oxidized, too. A car picks Scylla gassid, and we know that the aromatic carbons won't be touched because the stability of thes carbons due to the fact that they have their aromatic. So this is how we synthesize the first part for Now, what about the second products? We've never actually learned how to add nitrogen or n h two from using electric look aromatic substitution. We know how to do this from a on A and benzene ring. The has some sort of hey light on it. For example. It was bending with the kleiner bro Ming or flooring. We could do nuclear filic aromatic substitution because we know then that if he ad, for example, story a mouth and a man would be a strong base and you have a elimination of your leaving group. And in addition off your nuclear file being this on H to minus, however, that first requires generation off and a benzene ring with some sort of hey light attached to it, something more easier that we could do is add and nitro group to it, which we really know how to do through electrified aromatics institution and then reduce that nitro too. And in each too. So one way we could go about this is and you know, there are multiple ways that we can go about each of these. I'm going through one. But another way would be to use this than image to as your new profile and the engineering is electro filed by making this reacting the bending ring with, for example, seal too, and, uh, three. And then you would make some sort of bending derivative with a hail ID. And then you can't do a elimination edition nucleus like Aromatics Institution To get this edition products, I shall drop both ways socially, you see each way. So first I'll do the extra flick Aromatics Institution way in which they were going first, our natural group. So we know how to do that with Agent all three on DH H two s 04 and our ad one natural group on one of these carbons on the benzene. And then we're reduced this nitro to aiming by adding Hye Jin, I'm pleading carbon. I wasn't completely in Carmen. That will reduce on Lee are natural group and not the aromatic carbons to this aiming group. Another way we could do this now is through nuclear flick aromatic substitution. And now we could make our bending ringing to the electoral fall by reacting it with, for example, b r. Two d. E b r. Three, the way you get the addition of Bro Ming. But now who's issue this year? And this is that we can have Polly hello Jin Nation product being forms Now this would form a more messy product, and we have to isolate this model some student products here and then which then we could, for example, sodium name I as a strong base in ammonia. And then we can get our product like this. So there's two ways to get to this example. I think the Flicker Max institution weighs more clean just because with this abomination stopping the nuclear Philip aromatic substitution method, you will get products that have Polly Bowman Nation. And so you'd have to isolate for this model substituted bro mean derivative group to move forward with this reaction. The last example is there. Now. We have addition of two groups, and whenever we have additional tube is always better to add the electron donating first. So, just like in the first example, we first added a carbon group to the molecule on minimal carbon group. Are electron donating so they direct or so in Pera On this roaming group is in order positions. That means that we have ice Immers are that could be directed to have its plumbing. It's exclusively at this ortho position on top of the medic position, which we have to isolate out of. So if I begin with that with the bending rank, you first want hydrocarbon. So just like in problem, eh? Well, that one carbon is a fiddle craft calculation method. But now we won't oxidize it quite yet because we want that directing effect of the ch three for the Ortho in Para Positions. So you're not the broom, Ian, just like in this step here. But that's done in groups direct, cortical and pere. To get two products, you get the Ortho product. But then we would also get the pair I summer. But then we would have to isolate for this awful product to move forward in which then we can oxidize this carbon to get the fully oxidized product, just like in a which we use cam in all four tax information in a little bit of heat, just to make sure that flea oxidizes. And then we get this product of interest here

Here. The ocean is synthesize each compound from Nancy. Hey, B and C. So one by one, we're preparing each come down from Nancy E is the compound. Whenever your citizens in this kind of compound first off only have to remember that the order the group's present in the component Look at the molecule carefully when you look the product on and start making it So what I'm making striking from benzene. You have to see the nature of the group presenting the current Andi whether they're meditating or or to parity, and accordingly you will decide the burnt, how to introduce and at me. So here the first step is pretty craft reaction. That is Al collision on by that me. Tie it tight group we're introducing. So for that we need see it. Three. See it, see any English and self cleaning crew, right and hedges and by their The product which is formed is the kind men see after Dent. In the next step, we're in the same fertile cultivation. But here it is a solution so bad that C h t see double bomb Oh group is introduced in the monitor. So this is also close radius. It'll Clarence tickle in prison Self and I just Ellen include right and the product tree be bench drinking. And the entire group is already present on DDE It is or to protecting. So one of the expected product is this one and the better position you can give Jessica Tate. And after that, in the next we're doing the cellphone ish to surface Mission is with the hell off. So do and it's useful. And you must get to find a guarded. But no ladies or to Claritin, he take you and matter directing. See Double Bond ch three. So most from Emily s O T Edge Group should come on here. My book. It's so this is the compartment is formed No, go to the next be component to make starting from Benzie. So here may ease this compound striking province ing benzine Here also, you're taking care off that point that what is the nature of the book which is needed in the product On accordingly You're deciding the Patrick so here. But, uh, positions are presented. It is well, but I think we should be introduced first. And for that a civilization by three cartridge. So seeing Dean see double seeing Indians and self anhydrous a nuclear age. And but it assiduously known, is fault. Here, the tile and be our boat are actually orto better analogy. That is why we have to introduce Method Acting Group A sitting by stage. So here by this you're getting the hesitant Group C or C H. Lee. Once this is phoned, this is a little thin on once it is formed. After that, we're doing the ignition bye brewing and every beer t and add the middle position. You are expected no beer. So see Donald on war will be here. Scene three and B A should be committed after this, we need actually tight group here in reserve off a city group. So any reduction you can do you are doing here? Cleveland Sandra Dish. So that is zinc and mercury in prison, self, etc. And guided. The final product which is formed is this is very quiet product that is siege. Do see each tree and we are admitted. So this is Clements and production don't very important direction by that CEO can be converted to ceased. So you're getting to find an apartment be here starting from benzene. Now come to talk about it, see? And for Did our aim didn't get off. See adjourn seal and see the middle of the compound on. Decided to priority powder Introduced them So in the sea striking from benzene First he's by 18 oxide and aluminum crew. Right. You are introducing this siege siege You watch nor her name. You know this phone. And after that, in the next year Hello. Cloning imprisons off every city. So the couple from the bees siege drew ch doom Well inch and hedging after date You are doing control oxidation and the funny part Victory be by complete oxidation ch to which group can make an order Pursue it. So by control, Doc sedition You can gate c Chiku and hate yet And religion really mean as such The image So this is the final component is formed hurt or it is formed and

Okay, This problem is estimated to perform synthesis for each of these reactions. Okay, so first up, I have this metal fennel key tone, and we're going to transform that into this compound right here. Okay, So when we're comparing these two, we have the presence of this single methyl group gate. So that's one carbon. And then we have to add two more carbons were here 12 to that specific carbon. Okay, so luckily with my method finicky tone, there aren't very many options in terms of possible carbons to deep resonates. So we only have this one to deep rotate. And this is going to perform a very specific reaction, which includes a non nuclear Philip bulky base. Very strong, by the way, Such a L d a. So the reason that we use L. D. A s drawn very strong base is because we want to avoid having a self album conversation ourself alcohol addition with this molecule. Okay, so we don't use something like sodium hydroxide because it's simply not strong enough. We could get a mixture of products in which we have a couple of an ions and a couple of of these actual molecules, so we would risk having a self algal conversation or addition if we had a um not that strong base was l B A. So again, L d is going to go ahead. And deep protein ate every single one of these molecules, which is going to result in a deep ordinated, awful carbon just like this, so that deep rotated L for carbon is going to be considered nuclear filic. And we can go ahead and attack any elector file that we want essentially, And the elector fall that I want a tech is a, uh, elector fall that has two carbons in which I can have a leaving group on that second carbon. So, for example, because I want to add two carbons, I'm gonna have one two carpets and then attached to this carbon, for example, I'm gonna have a connection to a good leaving group such as I don. Okay, so this carbon nuclear fall is going to attack that carbon, and when attacks that carbon, I'm gonna have to release this item. That's a leaving group. And as I do that, I'm gonna form my desired product. Okay, so that's that reaction next up we have this one. Okay, so first up, I noticed that I have this ch two, um, in parentheses with five. So that might be a little bit confusing in terms of what's what. Something that just redraw this into its corresponding compound. Someone have ch 30 connected by carbon. Connects to my carbonell connected to 12345 carbons. Okay, so 12345 carbons were here. Okay. And then on that fifth carbon, I'm gonna have the connection to this carbon over here. What? Receives three. Okay, so that is my molecule. And we want to transform it into this cyclic structure here. Okay, so we see that we have this six member during, and then we have the connection to this effort group on the side of that carbon. Okay, so let's go ahead and hypothesize what could possibly do on this one? Okay. So because we do have these, um, five carbons between each of these cardinals, I'm going to go ahead and try to do in intra molecular clouds and conversation. So, for example, if I were direct this with sodium myth oxide, I would go ahead and deep protein ate the most acidic hydrogen, which would either be the hydrogen associated with that carbon or the hydrogen associate with that carbon Get because the small coast much cool, It doesn't matter. So that is going to perform a deep rogue nation in which I'll get this is my product with a set of impairs on that carbon right there with 123 for five carbons and then on the fifth carbon, we have a connection to my company slash Esther. Okay, so that is my products so far. And then this is going to perform the intra left there a pleasant conversation in which this carbon look, we fell, goes ahead and attacks this Carbonell. So I'm going to form a 123456 member drink. Okay, so it's gonna look like this. I'm gonna have my 123456 member today. So this is going to be 123456 attached to carve a number one which is right here on my left side. I'm gonna have the connection to my Esther. So just like this O C three. Okay, Carbon number two. I just have those 200 units would after it. That out three. Same thing for something. Five same thing. But then six is where we have a connection to my auction with a negative charge. So six has my auction with the neck of charge, and then we also have a connection to my oh, ch three just like that. Okay, so within a class in conversation reaction, we're going to have to move the electrons from this auction down to this single bond to make a double bond. And in the process of doing that, I'm going to have to move the electrons away from that carbon and onto that stage three as a leaving group. Okay, so this is going to be the resulting product. I'm going to have my six member during like this in which I have my carbonell slash Esther over here. No, CS three and then my other Carbonell over here. Okay, so that is my class and conversation. But again, we want to form this product right here. As you can see, we don't have that. So what I want when I do Instead, I want to go ahead and add something to this carbon. I want to get rid of this group. Okay, so this is going to be similar to my aceto acetic ester synthesis, in which I basically recognize that I have my Esther. I have my key tone, and this is going to undergo a acid base. Reactions in which a take off the most acidic hydrogen, which is flanked between these two carbon eels. Okay, so using something like sodium with oxide once again, sitting with oxide, I was gonna go ahead and take off that acidic proton just like that. There's gonna look like this and what you have the same compound is before six member during Carbonell over here. And then I have my Esther over here. But I have my lone pairs on this carbon. Okay, so those on Paris can go ahead and behave as a nuclear file to attack what? Whatever. I So please get in this case, I'm going to add these two carbons to it. Okay, so those two carbons are going to be attached by the formation of an s into reaction. Someone have stage two ch three connected to a good leaving groups such as Brahmi. And then this is going to add via an s and direction. Okay, I'm gonna attack that carbon with my carbon Equip, all thereby leaving the roaming as a leaving group. Case of this is going to be my product in which I have my six member during like this. I have my Esther over here. Oh, surgery. And then again, I have my two carbons over there and my carbon over here. Okay, so now we go. We have to go ahead and get rid of this Esther group. Right? We want to get rid of that entire thing, so it's going to undergo ahead, draws distraction. Which we're going to use. That's it. A three plus hydro knee, um, water and heat that is going to perform a headless distraction which essentially gets transforms this molecule, this Esther into a carb oxalic acid. So it's gonna look something like this, and I'm actually running out of room, someone to write it kind of small down here. Okay, so it's gonna be a six member during still, I'm going to have my carb, oxalic acid, my two carbons, and then my the company over there. Okay, so now we can go ahead and perform. I d card box elation reaction, which essentially gets rid of this group at the 02 and only to do that is use heat. Okay? And he is gonna take off this car. Looks like acid as a leaving group, and we're gonna have the resulting product, which is going to look like this. Okay, so that's that one. Let's move on to this. Second to last one. Okay? So as you can see, we have this Ben Zelda head, and we're going to transform it into this molecule. Okay? So as we can see, we have the connection of to this carbon. We have a connection to this carbon and this carbon case, we're adding two carbons to this Ben Zelda head. And how do we do that? Well, first of all, we have to recognize that one way to get carbons onto Appenzell divide is to perform a mixed conversation reaction. And that is going to be a situation in which we have this compound. Reckon with another carbon compound. Kate, specifically, it's going to be an Esther. OK, but obviously we have this car box so casted, but we're gonna transform that Esther into a car box. So casted. So, for example, I'm going to have direction of this Benzel of HUD with Esther. So as you can see, we're going to add again 12 carbons. We're gonna have some that looks like this. I'm going to have my ch three connected to my central carbon in the carbon. You and then over here we have the connection to my Esther is gonna look like this O c h three. So if I wrecked this been Zelda, hide with this, Esther in a basic medium, such as, um oh, ch three. I'm gonna have the formation of this product in which you have my Benz out ahead no longer. Benzel behead! I'm going to have it looked like this. Okay? So if the mechanism of that is confusing, basically all we did was we deep resonated this hydrogen off of my Esther. And then we ended up with a nuclear felt carbon on that awful carbon. Okay? And then the awful carbon went ahead and attacked this Carbonell of my benzel behind. Okay? And then we undergo a couple more reactions. But basically we end up with this product, okay? And as you can see, this product is very similar to this product. The only difference being that I have the presence of my Esther, my only three as opposed to my car box. So Kassid. But luckily all we need to do to fix that is undergo Hegel assists. So hydrologist involves the erection with H 20 plus hydro water and teach. Okay, so that is going to be my final production. Okay, next up, we have direction of this. So we have this compound eventually becoming this compound. Okay, so let's see what we have. You have to Esther's to Esther's, and then we have the eventual formation of this car box. Look, acid. Okay, so this is going to be very similar to a melodic Esther synthesis in which we don't have technically melodic Esther. But we do have something very similar. And that is because we have my to Esther's. And then we have this carbon flanked by two carbon eels. And those two cardinals are going to be very instrumental towards the acidity of this proton. So, using something like O. C three, my story is going to behave as a base to deep protein. Ate this acidic hydrogen. I'm gonna move the electrons onto that carbon. So the result of that is going to be this in which I have my ch three connected to my oxygen connected my Carneal connected to my carbon slash nuclear connected to my carbon slash Esther. Okay, because this carbon is not considered nuclear. Philip, I can go ahead and attack whichever carbon I so, please. Okay. So, as you can see, we have this carbon that's gonna be my nuclear fall. And in my product, I have that same carbon being right here. Okay, so this governor here corresponds to this carbon right here. So we have to consider what carbon Electra file we're going to add to this carbon nuclear file. Okay, so, as apparent by the product, we have the president of this cycle plantain. So I'm going to hypothesize just for now that we add a cycle plantain to that carbon nuclear fall. So that would mean that would have something like this. And if you have a five carbon compound and then we have a romaine right there. So this is all hypothetical. I would have a situation in which this carbon nuclear file goes ahead and attacks this carbon, resulting in the loss of this program. Okay, so that would result in this compound. And just for now, I'm gonna draw this and this as our because right now, I'm only worried about this particular carbon. Okay, somebody right down this, Would you have my are connected to my nuclear Philip Carbon, and then honest carbon? I have the connection to my cyclo Penton. Okay, so if we compare this compound down below to my eventual product, I know that this is not gonna be considered correct, because again, there's carbon corresponds to this carbon. And as apparent by our hypothetical product, we do not have the direct application of this cycle plantain to this carbon, but separated by a bond. Whereas in our actual products, the one that we want we had just have that direct connection of that cycle Plantain to this carbon. Okay, so we know that we just can't attack a, um, cycle pencil bromide. Okay, so we have to think of something better. Okay, So what I'm gonna have instead is something different and that something different is going to be a straight chain, so I know it will be a little bit confusing, because how can we have a straight chain that transforms into a cyclic molecules? But bear with me because it's going to be actually quite unique. And that is going to be somebody like this. I'm going to have a for carbon compound. 1234 And on the first and fourth carbon, I'm gonna be connected to bromides on each side. Okay, so there's going to be four performed in an s and two reaction just like before, in which this carbon nickel file attacks this carbon and that is going to result in the loss of this superb. Okay, So as far as the product goes, we're gonna get something like this in which we have ch three connected to auction connected to my Carbonell connected to my former nuclear Phil Carbon, which is now going to be added carbons two. So 1234 carbons. And then on the fourth carbon we have the connection to this brought me just like that. And then on this carbon, we have connect the connection to my carbonell slash investor. Okay, so that's the state that we're at right now. And as apparent by the product that I just formed. This is nothing like this, Okay? They're not even close. But that's just on the surface level. Because in reality, they're actually very close because all I need to do now is deep protein ate my awful hydrogen. And that is gonna be right here, because again, I want to form this cyclic compound. And if I have to deport me, the surgeon, I would end up with lone pairs on this carbon which can go ahead and attack this car compound. Okay, so it's going to be an intra Molecular s into reaction. OK, so it's going and try that out. I'm gonna have the Depo Nation using Oh, ch three, which is a relatively strong base. I'm going to get this product and what you have my c b C three connects to my auction connected to my Carbonell connected to my rest of my chain OSI tree over here. And then again, I still have my four carbon compound 23 1234 And then on the fourth carbon, we have my bro, me and then over here we have the presence of my lone pairs. Okay, so that's what I have right now and now we can go ahead and undergo my s interaction. So I'm gonna move these electrons onto this carbon. So that's going to be carbon. Everyone is going to carbon over 234 and five. And after attack that fifth Carbon, we're gonna have to leave. That brought me as a leading group. So the results of that should be as follows. I'll have my Series three connecting some oxygen connected to my Carbonell connecting to my carbon which behaved as a nuclear fall. In this case, it's gonna form my cycle. Pentti Just like that. Okay. And again, we're gonna have my Esther on this side as well. Okay, so right now we have this compound over here and we need to get to this eventual product. And only to do is the same reactions that we've been doing throughout this whole problem that is going to be a first of all hydro cysts in which we transform both of these Esther's into carb oxalic acids, and we're going to follow it up with a D card box elation, reaction. So first up, we're gonna have a three or plus, I drove him and water and heat that's gonna transform both of these Esther's into carb oxalic acid so that we can undergo d cor box elation in the future. So I'm gonna have to carve oxalic acids like this, in which I have my psych Lapentti over here and the other car box Ocasio over here. And then the very last step is just getting rid of one of these Karpov so acids as a carbon dioxide and that is going to be used with heat. Okay, so that should be the final synthesis of all these problems.


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Evaluaie 4juMe"nenaccaare (Hint Use the properies of loganthms,)IxSubstiblo orInxJnccx in Ihe integralIxux = - Ju duInlas Iilla wiln mcirccJudu- 3 Ruplacu In * irio siniply5(Inx?
Evaluaie 4juMe "nen accaare (Hint Use the properies of loganthms,) Ix Substiblo orInxJnc cx in Ihe integral Ixux = - Ju du Inlas Iilla wiln mcircc Judu- 3 Ruplacu In * irio siniply 5(Inx?...
5 answers
True or false ? Prove your answer!If t ∈ A and t > infimum A, then t/2 ∈ A.
true or false ? Prove your answer! If t ∈ A and t > infimum A, then t/2 ∈ A....
5 answers
Registered Voters vs. People Who Actually Voted in 201814,000 2 12,000 8 [ 10,000 { 8,000 13 6,000 1 4,000 J 2,000 72,0004,000 6,000 8,000 10,000 12,000 14,000 Number of Registered Voters from Each State in 2018 (in thousands)16,00018,000
Registered Voters vs. People Who Actually Voted in 2018 14,000 2 12,000 8 [ 10,000 { 8,000 13 6,000 1 4,000 J 2,000 7 2,000 4,000 6,000 8,000 10,000 12,000 14,000 Number of Registered Voters from Each State in 2018 (in thousands) 16,000 18,000...
5 answers
Marked out of 2.00Flag question If 15 P(5) = AP(1) in Poisson's distribution, what is the mean?Select one:a 3b. 4c.2d. 6e. 5
Marked out of 2.00 Flag question If 15 P(5) = AP(1) in Poisson's distribution, what is the mean? Select one: a 3 b. 4 c.2 d. 6 e. 5...
5 answers
Dctermine the exact value of the solution to the equation 823-1 = 5"1n 6 2 - lo5In 6 21n 6 n50 z =In6 _ In 5
Dctermine the exact value of the solution to the equation 823-1 = 5" 1n 6 2 - lo5 In 6 21n 6 n5 0 z =In6 _ In 5...
4 answers
Question 2.04 Compute - 98% confidence interval for the proportion of defective items in a process when it is found that a sample of size 100 yields 8 defectives:
Question 2.04 Compute - 98% confidence interval for the proportion of defective items in a process when it is found that a sample of size 100 yields 8 defectives:...

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