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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?

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

Explain why the connection without good excites and we've been excited. It's two different products. Let's look at the mechanism with our without backsides but the Nation actress first step and it produces Benzie like Come Pick a Time which is further stabilized by untraditional. Were fifteens in it in, for instance. Oh, structure was shows conjugation and this camera car time is most stable with public art time at this common, which is making conjugation with the benzene in. That's why this the assured direction off the reaction and a combination with BR minus gives you the major product in the prisons or both sides they have taken. Spacious is different. That's the radical of woman and unethical of woman. Also wants toe form Benzia political fishhook, and it's, ah, most able than medical at this carbon. For the same reason that would be liking education off the benzene green. And then on the next step over chain propagation, the medical reacts with them. HBR Junior is another. They are dark and gives the product

Hey guys! Leads to problem 50. The first question is way. Need to calculate the volumetric flow rate it is given that they put the problem. Is that a stripy? Therefore one to normal of guests. Apple pies 22.4 Major Cube and the number off most of gasses. The number off Muncey's that is getting in is the volume that's getting in, which is 3.74 given in the problem. Divided by 22.4 m too far. Guillemin therefore the number of most gasses 0.1 67 Kinnaman Fine minute. It means that every minute each minute 0.167 Philomel gas is getting in. Given the feed cast contents 22 more percentage of D. C. D. C s and 60% of the disease has reacted. Therefore, the most of these refugees That is second to the 60% age what is reacted, which is which means 0.6 multiplied by the mole fraction of D. C s and the total number of monster was seated and therefore 0.6 multiplied by 0.2 too much. That is the man fractional diseases and you can buy the total number of phones, which is your 0.167 Guillemin a minute. And from here we get to them most of disease strategies 0.0 to to to the moon. Four minutes since two months off nitrogen nitrous oxide reacts with one matloff diseases. Therefore the number off more off my dress up sides the number of most of nitrous excited that one which reacted is to multiple ratified a number of most of DCs that reacted. Which means that two multiplied by zero one has zero to do or 0.44 to the moment. One minute. Yeah, therefore, the amount of unrecognized Chris oxide. Let us calculate that that is the kind of the moon fraction off nitrous oxide and deployed with the number of moons that was needed minus the number off moves off nitrous oxide which reacted. It doesn't serve develops. Common fraction is 0.78 The total months. Caesar advanced 67 months kilometers per minute, minus the recommended 044 cumin for a minute. From here, we get the amount of underactive nitrous oxide ease 0.863 Kill them all per minute. Similarly, the amount of contracted DCs is the percentage 1% of D. C. S multiplied by the total number off moves minus the amount of disease that reacted from here We get the amount of 100 diseases Eupen 0147 Hilleman per minute. Since each more lost nitrous oxide reacted, it creates one mole of nitrogen and hydrochloric acid. One more off nitrous oxide produces one more off nitrogen on one more off hydrochloric acid. Therefore, the number off on love nitrogen and hydrochloric acid at one day at the same as the number of most off. I just excited one day and a number of months of hydrochloric acid at containing is is a country the number off off nitrous oxide which reacted, which is 0.44 kill the more for a minute. Now we can calculate the total number off. Yes, this will do it. They put the total number of most of us that one day. Yeah, yeah, yeah. It is the submission off down most of all guesses that pointing the number of months off DCs at 20 plants the number of months off nitrous oxide at 20 the last number of months off nitrogen, that pointy. That's the number of Monthsof hydrochloric acid at point E. Therefore, we can do the summation here. Therefore, the total number of months of gas at 20 is 0.189 Antiquated writing in verse, three small per minute. We can't kill them. One. Let's converted two months more permanent. Therefore, we can calculate the volume off gas as NRT, divided by P number of most 0.189 multiplied waiting in verse. Three more permanent. This constant is 62.36 multiplied waiting in verse three. Meet a cute door moral universe. One killed the Universe one, and the temperature given is 900. Did you sell shares, or 100% to 73 Children? Pressure given here is 600 for Milito or 600 for multiple written in verse. Three off. When we do this calculation, we get 2.2 900 goodbye. Tend to the bar for meter you for a minute as the volumetric for it. The next problem says what is the rate off organization? Let's calculate the rate off deposition. The partial pressure of D C s Can we calculate it? The partial impression off D. C S s. You can do the moon fraction off. Do you see us at point A. Multiplied by the total pressure and the moon fraction can be found by dividing them Number of months off the CS that 0.8 divided by the number of most off. Guess at one day want to graduate the total pressure The number of months of this is that 20 is 0.147 killing more than we need and total I want to go gas at one days 7.189 for the one for my neck The pressure is 604 Really drunk. Therefore, the passion pressure off DCs is 47 0 new little similarly, the partial pressure off nitrous oxide. Therefore, the function pressure of nitrous oxide is 276 mil It'll now the rate off deposition The relation is provided for innovative deposition. The question is are is the culture of 3.16 multiplied waiting universe For the partial pressure off D. C s multiplied by the partial impression off I just offside to depart their 0.65 So we have all these values here. Latest in some deck. The partial pressure on this is this. 47 in the passion pressure off 90 subsidies to 76. Once we do that calculation, we get the rate of deposition is 5.73 months of graduating Universe five. And finally, how thick is that? Sit on drugs. Sadly, questions see. From the rate of deposition, we can calculate the most soft silicon dioxide deposited after two hours. From the rate of deposition, we can calculate the malls off silicon dioxide deposited after drawers. Therefore, the thickness can we calculated as the Mueller Mass off silicon dioxide is 60 k g in 60 multiplied Veteran anniversary. As you 600.1, the specific gravity is given 2.25 and the density of water is Thank you. KC 1 may help you. Once we do this calculation, we will get 1.1 multiple waitin universe 5 m that's converted toe and strong on 1.11 to put right into the bar. Fine, I am strong. Is the thickness off the silicon dioxide there and this thickness of the ticker? The thickness would be taken towards the entrance off director because the partial pressure off disease and then I just oxide would be higher, something in a higher value of the deposition rate. That's right it down, resulting in a hang a lot of deposition red.


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