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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?

Predict the falling borders off penetration. Hey, for each group is Ah, Ortho PETA director, and she is free group that's met the director. So it's a case off consistent orientation. So that letter group enters with this Brothers Bay like trial is that met the director and this will free H is a metal director. Let's again consistent orientation in the latter group interests this position. See him in the struggle. Is it met the director. It directs into this position and horses figure is the offer. Period Director directs the order positions and the prayer position. The donor Rene's over except when it comes to orientation. Substitution to the Ortho position. Prevent Letter Group is not favorable because over stone edit from accepting activity or from in a group, so the product would contain the latter group into this position. They can be really a very minor impurities within matter. Group entering the close positions

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

So the first thing we're taking a look at it is not in technology here, so sensors were able to detect even the very small amount of chemical vapors. A few different equations that we'll need up on the screen while we take B is equal to pi the cube over six. We substitute in the Valley for volume in Equation one, you get equals density pie. Three. There's a six he had absorbed. That is Q. Is, um bracket that? And we are integrating within the limits. TMP I'm 25 degrees Celsius Have C p of the solid T d t at the doctor h hot bad the integral T v P T M p cp Liquid T t T at Delta H B. What we find is that we got an expression cube. There's 1.827 times 10 to minus 17 D A nanometers. Cute jewels. In the second part, we're rearranging the second equation that is up on the screen, this one just like this one now, using the next one. Where was solving for 40 nanometers? The minimum? Probably a on peace 1.552 times 10 to the four jewels per meter squared 23.9 watts, respectively. And then we we have 80 nanometers. Fn p. Minimum values are not playing 4783 times 10 to the four jobs per meter squared on 7.37 What's doing the exact same thing for 1 20 nanometers? Don't put 1/4 too One times tense. The four jewels for meat squared on 2.19 watts. So we use the laser power that is intermediate between those needed to pay a price. 40 and 1 20 nanometer particles such as the listed for 80 nanometer particles, so the large particles that have a greater diameter them on 29 m will remain in solution.

Explain why neither of those benefits just emphasize border from this starting material will not work, and so just something that will work. So the proposed calculation will place the Ethyl group in tow. Benzedrine, and it's on Ortho pair director. So the Clear Nation which followers will not go to the middle position when you see additional steps are out and first introduced cloying in clothing is still orthopedic director. So on the step off population, the group will not enter the. Does that mean that the position but they don't work, know what real work? So their strategy is for introduce a meta director into oblivion. First, that could be a later converted to the group out when you to perform escalation first. Is it a group? Is it meant to director? It's a business except no conduct coordination and now according intravenous position, and finally were reduced. The actual group toe every group using either Clemmensen reduction or business wolf reduction


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