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SYNTHETIC APPLICATIONS OF FRIEDEL-CRAFTS ACYLATIONS: THE CLEMMENSEN AND WOLFF-KISHNER REDUCTIONS Rearrangements of the carbon chain do not occur in Friedel-Crafts acylations. The acylium ion, because it is stabilized by resonance, is more stable than most other carbocations. Thus, there is no driving force for a rearrangement. Because rearrangements do not occur, Friedel-Crafts acylations followed by reduction of the carbonyl group to a $\mathrm{CH}_{2}$ group often give much better routes to unbranched alkylbenzenes than do FriedelCrafts alkylations. The carbonyl group of an aryl ketone can be reduced to a CH $_{2}$ group. (FIGURE CANNOT COPY) As an example, let us consider the problem of synthesizing propylbenzenc. If we attempt this synthesis through a Friedel-Crafts alkylation, a rearrangement occurs and the major product is isopropylbenzene (see also Practice Problem 15.4 ): (FIGURE CANNOT COPY) Isopropylbenzene (major product) Propylbenzene (minor product) By contrast, the Fricdel-Crafts acylation of benzene with propanoyl chloride produces a ketone with an unrearranged carbon chain in excellent yield: (FIGURE CANNOT COPY) Propanoyl chloride Ethyl phenyl ketone $(90 \%)$ This ketone can then be reduced to propylbenzenc by scveral methods, including the Clemmensen reduction (Sect. $15.7 \mathrm{A}$ ) and the Wolff-Kishner reduction (Sect. $15.7 \mathrm{B}$ ). A The Clemmensen Reduction One general method for reducing a ketone to a methylene group-called the Clemmensen reduction- consists of refluxing the ketone with hydrochloric acid containing amalgamated zinc. [Caution: As we shall discuss later (Scction $20.4 \mathrm{B}$ ), zinc and hydrochloric acid will also reduce nitro groups to amino groups.] A Clemmensen reduction (FIGURE CANNOT COPY) Ethyl phenyl ketone Propylbenzene $(80 \%)$ In general, (FIGURE CANNOT COPY) B The Wolff-Kishner Reduction Another method for reducing a ketone to a methylene group is the Wolff-Kishner reduction, which involves heating the ketone with hydrazine and base. The Wolff-Kishner reduction complements the Clemmensen reduction in that it is conducted under basic conditions, whereas the Clemmensen reduction involves acidic conditions. The WolffKishner reduction proceeds via a hydrazone intermediate (Section $16.8 \mathrm{B}$ ) that is not isolated during the reaction. Ethyl phenyl ketone can be reduced to propylbenzene by the Wolff-Kishner reduction as follows, for example. A Wolff-Kishner reduction
(FIGURE CANNOT COPY) Hydrazone intermediate (see Section $16.8 B)$ When cyclic anhydrides are used as one component, the Fricdel-Crafts acylation providcs a means of adding a new ring to an aromatic compound. One illustration is shown here. Note that only the ketone is reduced in the Clemmensen reduction step. The carboxylic acid is unaffected. The same result can be achicved using the Wolff-Kishner reduction. (FIGURE CANNOT COPY) Benzene (excess) Succinic anhydride 3-Benzoylpropanoic acid (FIGURE CANNOT COPY) 4-Phenylbutanoic acid 4-Phenylbutanoyl chloride $\alpha$ -Tetralone Starting with benzene and the appropriate acyl chloride or acid anhydride, outline a synthesis of each of the following: a. Butylbenzene b. (FIGURE CANNOT COPY) c. (FIGURE CANNOT COPY) Diphenylmethane d. (FIGURE CANNOT COPY) 9,10 -Dihydroanthracene THE CHEMISTRY OF... DDT Aryl Halides as Insecticides Insects, especially mosquitoes, fleas, and lice, have been responsible for innumerable human deaths throughout history. The bubonic plague or "black death" of medieval times that killed nearly one-third of Europe's population was borne by fleas. Malaria and yellow fever, diseases that were responsible for the loss of millions of lives in the twentieth century alone, are mosquito-borne diseases. One compound widely known for its insecticidal properties and environmental effects is DDT $[1,1,1$ -trichloro-2, 2-bis(4-chlorophenyl)ethane]. (FIGURE CANNOT COPY) DDT $[1,1,1$ -trichloro-2, 2- bis(4-chlorophenyl)ethane] From the early 1940 s through the early 1970 s, when its use was banned in the United States, vast quantities of DDT were sprayed over many parts of the world in an effort to destroy insects. These efforts rid large areas of the world of disease-carrying insects, especially those responsible for malaria, yellow fever, sleeping sickness (caused by tsetse flies), and typhus. Though it has since re surged, by $1970,$ malaria had been largely eliminated from the developed world. According to estimates by the National Academy of Sciences, the use of DDT during that time had prevented more that 500 million deaths from malaria alone. (IMAGE CANNOT COPY) DDT Eventually it began to become clear that the prodigious use of DDT had harmful side effects. Aryl halides are usually highly stable compounds that are only slowly destroyed by natural processes. As a result they remain in the environment for years; they are what we now call "persistent insecticides" or "hard insecticides." The U.S. Environmental Protection Agency banned the use of DDT beginning in 1973. Aryl halides are also fat soluble and tend to accumulate in the fatty tissues of most animals. The food chain that runs from plankton to small fish to birds and to larger animals, including humans, tends to magnify the concentrations of aryl halides at each step. The chlorohydrocarbon DDT is prepared from inexpensive starting materials, chlorobenzene and trichloroacetaldehyde. The reaction, shown here, is catalyzed by acid. (FIGURE CANNOT COPY) DDT [1.1,1-trichloro-2,2bis(4-chlorophenyl)ethane] Estimates indicate that nearly 1 billion pounds of DDT were spread throughout the world ecosystem. One pronounced environmental effect of DDE, after conversion from DDT, has been in its action on eggshell formation in many birds. DDE inhibits the enzyme carbonic anhydrase that controls the calcium supply for shell formation. As a consequence, the shells are often very fragile and do not survive to the time of hatching. During the late 1940 s the populations of eagles, falcons, and hawks dropped dramatically. There can be little doubt that DDT was primarily responsible. DDE also accumulates in the fatty tissues of humans. Although humans appear to have a short-range tolerance to moderate DDE levels, the long-range effects are uncertain. Study Problem 1
The mechanism for the formation of DDT from chlorobenzene and trichloroacetaldehyde in sulfuric acid involves two electrophilic aromatic substitution reactions. In the first electrophilic substitution reaction, the electrophile is protonated trichloroacetaldehyde. In the second, the electrophile is a carbocation. Propose a mechanism for the formation of DDT. Study Problem 2 What kind of reaction is involved in the conversion of DDT to DDE?

So this is a long problems, so I'll throw on some basic first. So what this is going on about is there are different combinations of proteins that they are testing. In this experiment, thes exists as timers, meaning that the T one are one is a single protein, and we're saying it's bound to another single protein, and these come as a complex. So these are an example of the kind of die MERS we're talking about. Will say It's a T one R one protein, and it's bound to a T. One are, too. There's, too, so it makes a single diver. The response. Onley happens because thes two proteins air together, and they do not exist in the membrane as a single protein, eliciting a response. The other thing they're doing is they are knocking out the presence of these proteins in the mice. So what they're doing is there finding the genes that produce these proteins. It's a one, and they're making different kinds of mice that don't have these proteins. So what they're doing is they're knocking out, so they're preventing these proteins from being made. One of each of t one are won t one are two and T one r three, and they have a special fourth mouse where they knock out both t two t one are two and t one r three. So in problem A, they're proposing to different models for how our taste receptors work. They're saying that there is a cell model and that there's a receptor based model based on how our tastes work. The cell model is saying that we have taste cells, and each of these taste cells has one specific type of dime. Er. So we're saying this first cell has a t one are one and we'll see a T one are two receptor and no other kind of diver. A different tastes cell. We'll say we'll have ah t one are one and a T one r three. These each has specific different types of cells. So we're saying that the tastes thes different cells react. Thio will be different and independent. The other kind of model they're proposing is that each of our taste cells have multiple sets of those dime er's. So they're gonna have each combination of these, and the signal it sends out is going to change based on which receptor for which timer is activated. So it's gonna have the whole mixture of these reactions. It's going to be the whole compilation of these different proteins in their giant reforms. So it's They're noting that in previous work they took individual cells and they isolated them, and they probably ran a gel electrophoresis to see what kind of proteins they could find from each cell. So they ran multiple gels, and they found out that between different cells taste cells, they had different proteins. So we're going to say this one did not have the t one are, too, and this one do not have the t one r three. So since we're finding cells that do not have a mixture of all of the proteins, and they each Onley have certain types of proteins, the previous research they've done supports the cell theory where each taste cell is different in their protein contents, rather than containing all the dimmer combinations at once. Problem being, they're testing the different types of taste. They're testing salt. They're testing bitter. They're tasting you, mommy, which is kind of like the flavorful nous you find your needs and they're tasting sweet. So they're testing them on knockout mice. Um, you'll remember that the t two t one are too 21 r three is responsible for sweet and the t one are one. T one r three is responsible for you, Mommy. So in the knockout mice they've had where they've knocked out, say the combinations of these proteins all those knockout mice. Even if they don't have these special combinations of diners in them, they can still taste salt and bitter. This is kind of proposing that even without those special dimmers, you're still able toe perceived those different tastes of salt and bitter. This means that all our tastes aren't dependent on the timer's that were knocked out in this representation and experiment in part C. They're showing us a graph of the response for a new mommy taste and knock out mice where if you eliminate either t one r three or if you knock out t one our wine, you're not going to get any response our extra licking from an umami flavor. You'll also note that for the controls and the experiment, they used I m p to increase the flavor of umami, and they used a melon I'd to reduce the salty flavor. This is just toe help control the licking the mice might dio for the ingredient they used to prevent the vice from liking it due to a salty flavor. They're controlling it so that Onley the umami flavors what the mice are gonna lick for. So for this model, it's more representing that mommy has to exist in the dime. Reform of tea one are one T. One R three To get any sense of umami flavor. If you knock out either of these proteins, you can't taste umami. So this is applicant to both cell models because regardless of whether the actual sell, your experimenting on has just the t one are won t one r three for a mommy or has the mixture of all the different dime er's. If you knock out either of these two proteins that make up the dime. Er, you're not going to get any response of umami from either of them. So you know that Mommy has to come in the diamond form, and regardless of whether the diamond exists in just one type of cell or exists in all type of taste, cells. You're not going to get a response if you remove that diamond. Okay, Part E were given another model for a sweet taste. This one's a little bit different than your mommy. Um, here you have the wild type or the t one are one wild type. Just means none of the proteins have been removed, so they have all the different types to u one R one t one are two and t one are three, so they're just normally born, not genetically modified. The other lines represent the removal of t. One are two on lee T one are three on lee and both t one are too t one are three that make up the sweet flavor timer. This model is more representing that. If you remove any of these processes, T one are two or tty one r three. You're still not going to get as much of a sweet flavor. So again, you pretty much have to have the dime er to get that full sweet flavor taste. And if you knock out either one of those proteins, your ability to check tech these flavors is greatly reduced. The only difference here is that the X axis measures the concentration of the material and at very high concentrations, you can perceive the flavor of sweet to a small extent as long as you have either the T one are two or the t. One are three present. So even if for some reason you can't make the diamond for it if you have t one are too. You can still purse. We've seat suite, which is unexpected. That kind of it's a lot different than the umami, where you must have both in order to perceive the taste. So moving on to part F here we have perceiving the taste of sucrose as sweet. Um, this was what I was referring to earlier. If you don't have both of the proteins, T one are two and t one are three. You can't persuade sweet it all, but it's unusual that if you have just a single of one of the proteins, it doesn't have to exist in the diet reform. It can somehow exist, probably with a T. One are, too, and some other sort of protein that they're not testing in this experiment. Lastly, in part G there, substituting kind of the flavors that are being perceived. They're using tetracycline, which is an antibiotic, so it's not gonna have any kind of particular flavor. They're using it to substitute a sweet taste, and they're not going to use any kind of sweet ingredient. Instead, what they're doing is they're altering the protein so that when you apply Tetra cycling to the dime er you're going to purse, we've it perceive it as a sweet flavor rather than no flavor at all. In this circumstance, it is kind of proving that you don't need specific substrates. Are substances to stimulate the diner protein to get the response you'd expect? And it's saying that you can use other substances instead to trigger the response. That's kind of not what they're going for the experiment. But it still manages to prove what the scientists are thinking because as long as you stimulate the dime er, regardless of what you give to it, it's going to trigger response that your brain perceives as flavor. So it's saying that although our dime er's may not need a certain sweet flavor in order to send a signal, it's saying that you need a signal to perceive the taste of sweet. If there's no signal sent by the protein, you're not going to get that flavor being perceived

So for this question, we're looking at an experiment run by scientists checking to see how B 12 was controlled and its effects on different chemicals in the body. So I actually pulled this table from the published experiment because I thought this would be easier to understand than the table provided. So here you can kind of just ignore the tumor necrosis factor Alpha, because we're more concerned in this question about leptin, M C P one and I 06 So here you can see you have both the four weeks reading when they're being fed on either their limited diet or your giant without any B 12 and their results at 12 weeks. So they're limited. Diet means they have some B 12, but not very much. It's decreased, whereas the non diet means they have little B 12. But they're fed pectin in their diet, which inhibits the absorption of B 12. So any B 12 found in their diet is not going to be absorbed for the most part, So here they are, basically saying they have no B 12 in their diet, So if you look among each of these, you can see that the limited diet typically has a small increase in each of these depict cytokines, whereas the nun or no B 12 in the giant causes a larger increase for the most part in each of these chemicals. So for part A, they're asking about the significant difference between the control group and the limited or no B 12 diet and their difference between each of them. So the way to go about this is to look at the mean value, which is going to be that provided value and to add or subtract the standard deviation from each of these and you'll get a range of numbers. So for the control group here, you would get about 1 13.5 2 200 no. 1 20.5, and you have to do this for each of these groups. So for the Limited, you would get one 20 5.9 to a range of 1 36.1. So here you just have to expand the mean with the standard deviation range to get a range of values. And this is because this standard deviation is telling us where the true mean value of the real concentration of these molecules lies in each of these groups. So because we have a small sample group, the standard deviation between each of these animals or the mean value they get for each of these animals actually ranges by a a pretty significant amount. So if you do that for each of these values to get a range, you should get a table that looks like this. So here you be able to see these least amount of range for the mean value and the highest amount of range. If you're looking for a significant difference, you're looking for a value that has no overlap. So here you can see that the highest value for your tumor necrosis factor for the control group would be about 120.5 pictograms familiar, Whereas the smallest possible mean value for the limited diet of tumor necrosis factor would be 125.9 pictograms familiar? So you know there's no overlap between the true mean value between these two groups, so you can say for certain that your limited group should always have a larger tumor necrosis value factor than your control group. This is opposed to say the left in value where you do have this overlap where the max value for the control group is higher than the minimum value for the limited group. So here you wouldn't be able to say for certain that there was a statistical difference between the two. It's possible that the rats in the A limited group will have a mean value of 5.6 people grams per mil leader or milligrams familiar, I believe. Whereas your control group could have a 5.7 normally so there you'd be able to see that there is practically no difference between the two and that one value is not higher than the other. So if you look for all these missed overlaps in the week four column, you'll see that I've marked them with this Blue Cross. So here the statistical differences are mostly going to be in the non category. So here it would be your statistical differences in the leptin, M. C, P one and I. L six for the non group. Whereas the limited group should have no statistical differences at the four week mark for Part B. We're looking at that statistical difference at Week 12. So again you'll see. These are, for the most part, marked in orange, but you want to be careful. So at week 12 again, all the non group will be statistically significant different. You'll also have a statistical, significant difference in the aisle. Six for the limited group, the leptin group for the Lemonade group is slightly overlapped, so you would not be able to say there's a statistical difference. But more than likely there is, but you're still not able to conclude that for sure. So for Part B, you should get all the non group is just significantly higher as well as I L six is significantly higher in the limited group at Week 12. For Part C. They're looking at a statistical jump between Week four and Week 12, so those are marked with the Red Cross, so you can see there's no overlap between Week four and Week 12 in the Limited group for the leptin values. You can also see it in i 06 of the limited group and in the leptin values of the non group. So here your answer for C is going to be the leptin for the non group, the leptin for the Limited group and the Aisle six for the limited group. Yeah, for part deed. They're asking us why we have these increased values of leptin, M C, P one and I'll six. So leptin is for hunger, so you can imagine when an individual is not getting their B 12, their body could be telling them to eat more so they get this nutritional value of B 12, whereas for M. C P one and I 06 These are more related to the immune system, or M. C. P one is found in mono sites, which is for cleanup of dead cells and such. My guest best. Best guess for why these are increased is because B 12 is an important factor inside of your red blood cells, so it's required to make the same molecule that's going to bind iron and make up hemoglobin. So if you don't have the proper amount of B 12, your red blood cells actually enlarge and you get a macro citic anemia. When your red cells are enlarged, it can be harder for them to pass through blood vessels, and they're probably more likely to be eliminated inside the body and fragment and release their contents. So here you can have the mono sites cleaning up your red blood cells. And, of course, your I 06 will respond to the contents of the red blood cells. With that increased immune response, those are my best bets. For part being, this question is a little strange. They're asking us if a lack of pathogens are positive for the increased auto immunity in developed nations. So this would be like France Germany. The U. S place is considered highly civilized. That will get their proper amount of B 12. And likely the reason they're bringing this up is because these immune adipose cytokines are going to be lower in these individuals. That's actually don't meet their B 12 requirements. So they're placing the conjecture that because these immune chemicals are lower, we don't have as much of n immune response to keep us healthy. So here they say that the M C P one and the Aisle six would be decreased and may have some effect on our immune system. However, autoimmune diseases typically have other factors than these regulators of immunity, so it's not impossible to rule out the effect of a proper B 12 diet in lowering these sort of regulatory molecules and possibly developing an immune autoimmune reaction from these molecules. But it's probably more reliant on other factors, such as exposures to other molecules or mutations, or to other factors of diet or obesity in developed nations.

Explanation for part A a style Cohen design A derivatives. Are he used then free 50 acids. Sins. The former his style is a tile. Coenzyme a can be transport it in the mitochondria and the later is we will ever in the cytoplasm. And the experiment. The researchers? Yeah, he used to read Oh, God Lever Michael Corn Andrea Yeah. Explanation for part B. None half lower. Molecular weight. A style coins. I'm a very great use. Were found with Ciccio Troy. Oh, I said I'll coenzyme Since this David use he is the first conversion can Virgin toe is a dial. All right. Coenzyme air. Y yeah. Vita oxidation. Yeah. Explanation for part C Both meet to roames off bitta oxidation explanation for party. They get him off drones is higher, then cease derivatives. Do you do the difference and configuration and shape off the and Zain Substrate complex explanation for part e The substrate for l C Eddie are we and C A. D is different friends here. Kinetic parameters oh, are used for different show processing off to explanation for a party. The kinetic her majors detective that says all right, I zumer is a better substrate in L C early and we we l see Eddie, do you to this? It came can be concluded there. There are fewer since I Zomer eyes Omar's after in cu patient off red liver. My took on Rhea Yeah. Answer! What part edge the Trans Faked can be Take a melodic in the body They okay can be broken Dawn by the cells How able in a slower read compare to see spate


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(0/1 Points]DETAILSPREVIOUS ANSWERSSCALC7 11.1.015. 2/10 Submissions UsedFind formula for the general term & the sequence, assuming that the pattern of the first few terms continues: (Assume that n begir 2 , 56 ' #-Need Help?Je R0 aEhibmti AnaurVanvig Sued Won Raneitfo Last Rexpona
(0/1 Points] DETAILS PREVIOUS ANSWERS SCALC7 11.1.015. 2/10 Submissions Used Find formula for the general term & the sequence, assuming that the pattern of the first few terms continues: (Assume that n begir 2 , 56 ' #- Need Help? Je R0 a Ehibmti Anaur Vanvig Sued Won Raneitfo Last Rexpona...
5 answers
A roller-cousler vchicle has $ mass of S0Q LE whcn fully loaded with passcogcrs_ (See #gurC ) I( the vchicle has apecd of 8,0 me AU polnt _ whal /s the force of the track onthe vchicle, N; AF that point?8.1 KN{4.9 kN1,7 kN6 2 NZero:
A roller-cousler vchicle has $ mass of S0Q LE whcn fully loaded with passcogcrs_ (See #gurC ) I( the vchicle has apecd of 8,0 me AU polnt _ whal /s the force of the track onthe vchicle, N; AF that point? 8.1 KN {4.9 kN 1,7 kN 6 2 N Zero:...
5 answers
Find an equation in spherical coordinates for the surface represented bY the rectangular equationY =7
Find an equation in spherical coordinates for the surface represented bY the rectangular equation Y =7...

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