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4z5oo(2) 5.027 12 00 9Wnalanha pemcentdntocen n NH;? Atj04 1074 alom? (1) 24 30 96 0J eWnaliy- aterao 24.30 aMu Eibrinns L In U? Khal / munt of one mole al tne 0411...

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4z5oo(2) 5.027 12 00 9Wnalanha pemcentdntocen n NH;? Atj04 1074 alom? (1) 24 30 96 0J eWnaliy- aterao 24.30 aMu Eibrinns L In U? Khal / munt of one mole al tne 0411 pd Io h4mo2s subslarce weighs 02.5 4312.28 40" 0mol (212.17 ol qlmc Jior (1) 4. 38 707'0 mc (210.183 0.CA14 Diicnon 4110.0457 mol Cakulai man A mdas ol xoncn 117.82 (3) 118.14 Jimal 114.11 9imd (21,220.22 gimcl Molr mus{ (NHAhSO Calculaly (4) 132. Ymoi moge (21 9.12 moles INhhL? (114.5 How many mDes of H etoms are i 4 56 mc

4z5oo (2) 5.027 12 00 9 Wnalanha pemcent dntocen n NH;? Atj04 1074 alom? (1) 24 30 9 6 0J e Wnaliy- aterao 24.30 aMu Eibrinns L In U? Khal / munt of one mole al tne 0411 pd Io h4mo2s subslarce weighs 02.5 4312.28 40" 0mol (212.17 ol qlmc Jior (1) 4. 38 707'0 mc (210.183 0.CA14 Diicnon 4110.0457 mol Cakulai man A mdas ol xoncn 117.82 (3) 118.14 Jimal 114.11 9imd (21,220.22 gimcl Molr mus{ (NHAhSO Calculaly (4) 132. Ymoi moge (21 9.12 moles INhhL? (114.5 How many mDes of H etoms are i 4 56 mclos 18,39 males (4) 18.24 moles Vat is mdecular Muxt 0l37r cmol Homo C,nlln compound with cmoinca CikeBl CAHADI t 4iCHebl C H-gte Wmr s0 (21M"" = lommula? Hcs04 specles presenl in Tan aquaqus sdnbc Idanily te tor inG (4va"" and 04 (3) Mg" fom nirc orde aalci Vaoc reacts wth Orygen (NA, (o Ammoniz 64,0 aicuss reagenn? 4NHL elwed Teacl whch is Ic mol NH) and 5.0 mol Tanem CilcocHE (acetc acid) (Jco Mo (ultlo 02 suang eleclrer o? Lompundt Knch the lolloxting Koh eolutcn m Euled ChCH07 lethanoi FNO sonlion when 70.0 93740 HNO; 71126 M 70175 Ihe ne * malanl 1500 mL? Wha: Vater lotal volume ih pury mued? Mirj at ZnSOdag) end Meohen) Euba eDrcuto 179 occur when solutions h form; Mae"and S08"= Noansnei cotec: the following wl plucipiate 4ZnCl Which = pestto wll form ard Cr wWl be (2) HCIO: Drecntele of MgSO- wll form seale? (1) HCO precipiiate oudaten chlonne oltne (ollowing Anich 2NaBr(5), ' 21. For_ (4ACiIO ZNals) = Br 91 (31 HOO: {edcton rnttened number clectrons CoChed) (41ZnCatal - cug) (31 3 Znls) - (21 2 repheaneni retchon ZnCllaa) following single Coclad) " lodbel Encun) Predict the productuof the {(2) Cots) (best Gercroed ercbon reaction occun ZH,O() is E Cacenpoenen (1) No K50 {a1 ASO4aal (dbnlacemtnt rucion ZKOHlaq) - hydrogen reaction = 24. The reaction #sO (4) Cr ncutalization = reacton oridation-rcducton _ (T)H" all acid solutons consbluent in [ common E 25. The 0 237



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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?

Using it isn't serious and b r plus, as an example on a profile. Explain why the hydroxy group in Funeral is actuator and Fourth of Prayer. Oxygen in the first group restroom won't compare, and they can be donated to Vedrine by the residents donated effect, which in creatures that been seen in with electoral and make it more susceptible toe therapeutic substitution. They and it over foreign affairs off oxygen because off its electro negativity that's inducted, defect cannot contract the stronger residence defect. And this The net effect is even stronger in the Sigma products, which is intermediate in the traffic automatic substitution. So it's an activator. No, let's write free Christmas tortures over its cinema complex when benzene with B R plus. So there was the charge is Jellicle ized Dream two orphan and one pair position. With respect to Borman. No, let's place for H in the fourth position and see if it's a good or the director or which group is next through the crab. With the price of charge, there's a excellent opportunity to forced organization by the business donating effect. So which group is an official order for director? No, let's please the ritual in the middle position. Now you can see that in my the reason structures or each group is attached to the carbon with a partial positive charge. So the actuated defect or for age, so the middle position is much weaker. A little still activation. But it's Rica than actuacion through the or the position. No, let's drive a planner or hate your job. The pair of age group. Now it's again attached carbon with a partial positive charge. So documentation is begin very official, because off the residence, the nation off the long compare on oxygen so the age group is also in a better direction.

Predict products or the fallen reactions. Dorian L. Sulfuric. That's Ah. So finish which goes toe the pair in the positions because 63 group is a hearted contributed a dollar dessert. Is it liberation? The car parks. A group is a resonance except her. Yeah, the try substitution goes to the net position Bremen nation off matter benzene. The letter group is an inductive, except er and business, except er so substitution goes to the net position insulation or for isopropyl Benzia I support group. That's ah Harper conjugated donor. So substitution goes toe the parrot in Ortho position. However you to the stereo hinderance imposed by the I support group. The author I, Samir is almost not existent. Just traces its most repaired. I, Samir.

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

Predict results for the two foreign reaction. One finger prep. In with its shell, it's you will return it while a figure prepping and bread use a more stable Ben Zizek crocodile ritual. Capture CR minus on Give the world the alternative. Kavika Tile at this carbon would be less stable because of the leg off education with it benzene for hundreds inoculation. The reaction proceeds through Make uranium on the press. The charge will be distributed between America and roaster gerbils, and this carbon will have more positive charge because it will be better. Gillick allies back in education with the benzene. So this position, well being attacked with water with the bunt with maker comes off on America is a benched through the other carbon and then deport the nation and removal, or for America by reducing agent Junior it in Alcohol River Bridge Group in the bin Zigic position


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