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Md4-nitrobenzoic accthyl-4-nitrobenzoateExlnction of 4-nitrobenzoic acidand ethyl 4-nitrobcnzoate Dissolve gof a~50.50 mixture of 4-nitrobenzoic acid and ethyl-4-ni...

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Md4-nitrobenzoic accthyl-4-nitrobenzoateExlnction of 4-nitrobenzoic acidand ethyl 4-nitrobcnzoate Dissolve gof a~50.50 mixture of 4-nitrobenzoic acid and ethyl-4-nitrobcnzoate mL of ethyl acetate Shake the omganic solution with 15 mL of 0.1 MNaOH in separatory funnel and then separate the two layers into two different; labeled beakers Retumn the organic layer the separatory funnel and repcat this extraction procedure tWo more times; Combine the #qucouS extracts and re-acidify this solution using

md 4-nitrobenzoic ac cthyl-4-nitrobenzoate Exlnction of 4-nitrobenzoic acidand ethyl 4-nitrobcnzoate Dissolve gof a~50.50 mixture of 4-nitrobenzoic acid and ethyl-4-nitrobcnzoate mL of ethyl acetate Shake the omganic solution with 15 mL of 0.1 MNaOH in separatory funnel and then separate the two layers into two different; labeled beakers Retumn the organic layer the separatory funnel and repcat this extraction procedure tWo more times; Combine the #qucouS extracts and re-acidify this solution using dilute HCI precipitale the 4-nitrobenzoic acid: Isolate the carboxylic acid (organic acid) by vacuum filtration. Dry the organic solution 4aro anhydrous MgSO and remove the solvent under reduced pressure - obtain the organk ester (neutral organic) which should be trunsfemed watch glass and allowed crystallize: Record the mnasses the isolated compounds and compare the mass the mxtun originally ablained, Report percent Tecoven} your report and fully discuss your results_ Salety: Always wear approved eyewear when - the laboralony - recottueuded that you wcar appropriale gloves (nitrile or latex) when working the lahoratory . Hydrochlorie acid and edt hydroxide Cause cncmica bums theskin . Ii physieal contact made with any cheticals, flush the affected arca with water for . least _ mS Always vent the scpartory tuinna away from other people and into the fume hood Icaroerdotocemq745 40 command option command anton



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SULFONATION OF BENZENE Benzene reacts with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is sulfuric acid that contains added sulfur trioxide $\left(\mathrm{SO}_{3}\right)$ Sulfonation also takes place in concentrated sulfuric acid alone, but more slowly. Under either condition, the electrophile appears to be sulfur trioxide. (FIGURE CANNOT COPY) $\mathrm{SO}_{3}$ is protonated to form $\mathrm{SO}_{3} \mathrm{H}^{+}$ (FIGURE CANNOT COPY) SO $_{3} \mathrm{H}^{*}$ reacts as an electrophile with the benzene ring to form an arenium ion. (FIGURE CANNOT COPY) Loss of a proton from the arenium ion restores aromaticity to the ring and regenerates the acid catalyst. In concentrated sulfuric acid, sulfur trioxide is produced in an equilibrium in which $\mathrm{H}_{2} \mathrm{SO}_{4}$ acts as both an acid and a base (see step 1 of the above mechanism). All of the steps in sulfonation are equilibria, which means that the overall reaction is reversible. The position of the equilibrium can be influenced by the conditions we employ. (FIGURE CANNOT COPY) If we want to sulfonate the ring (install a sulfonic acid group), we use concentrated sulfuric acid or- -better yet- -fuming sulfuric acid. Under these conditions the position of equilibrium lies appreciably to the right, and we obtain benzenesulfonic acid in good yield. If we want to desulfonate the ring (remove a sulfuric acid group), we employ dilute sulfuric acid and usually pass steam through the mixture. Under these conditions with a high concentration of water the equilibrium lies appreciably to the left and desulfonation occurs. We sometimes install a sulfonate group as a protecting group, to temporarily block its position from electrophilic aromatic substitution, or as a directing group, to influence the position of another substitution relative to it (Section $15.12 \mathrm{B}) .$ When it is no longer needed we remove the sulfonate group.

Okay, so we'll start with our first Lewis structure. Carbon is a central atom and it forms four bonds. We're told one chlorine is on each carbon with the other before hydrogen will be attached in this way. So there is your first lewiS structure and the second one we've got carbon and carbon and a corinne And two more hydrogen. And since carbon wants four bonds, this is going to be a double bond here. Okay, so those are your LewiS structures. This has a carbon carbon bond order of one, it's a single bond and this has a carbon carbon bond order of two, which means it's a double bond. So we're gonna try to use the bond energies to find the heats of reaction. So it's easiest to sketch out each structure here. So you can keep track of the bonds that you are breaking and making. So in this case are heat of reaction is the bond energy. Oh, all the reactant bonds minus all the product. Bones. So this is going to be there's four carbon hydrogen bonds because the carbon carbon double bond, Kloza, chlorine, chlorine single bond. And then we'll subtract over here on the right for carbon hydrogen bonds And we'll subtract two carbon chlorine bonds and a carbon carbon bond. You can see that these will cancel out and then we'll just look up our bond energies And see what we get. So 6 14 Close to 42 for the chlorine chlorine bond -2 times are carbon chlorine bond, which is 348. So that will give us negative 1 48 killer jewels for that reaction to the second reaction. Now we're going to take this is now a reactant. Again, it's worth it to take the minute to sketch out what you're doing here to make sure you don't miss anything. But this is an equilibrium with this year. This is your C two H four and your hcl. So our heat of reaction is going to be four carbon hydrogen bonds plus a carbon carbon bond of course to carbon chlorine bonds. And then we're gonna subtract for carbon hydrogen bonds. We'll subtract the carbon carbon double bond and we'll subtract and each cl bond you got the elder. So if we plug in all those numbers here again, these two are going to cancel out. So 3 48 for the carbon carbon supposed to Times 3 28 for the carbon chlorine. And then we'll subtract 6 14 for the carbon carbon double bond And we'll subtract 4:31 for the last one. So this will give us negative 389 Killer Jewels. So those are your entropy changes for those two processes estimates because we use bond energies. Okay, so we're going to talk about how the yield first of all of this is affected by temperature and by volume. Well, this is an exotic thermic reaction. So our heat is over here. So we want to think of ways where we can increase the yield of our product obviously. So we're gonna want to decrease the temperature. If we decrease the temperature, the reaction will shift to the right and we'll produce more products. Mhm. For volume, we want to look at the reaction is going to shift to whichever side. If I increase the volume more moles of gas. So this side has two moles of gas And this side has one ball of gas. So I want to do something to cause it to shift to the side with one mall because that's our product. So we're gonna want to decrease the volume. This will cause it to shift to the side with fewer moles of of gas, which in this side is to the right, so those two changes would cause you to form more of your product. Similarly with the second one, it's also eggs a thermic. We just found the heat. So we're going to for the same reason, want to decrease the temperature. You're going to increase the amount of the product which you're trying to make and with the volume we're going from one mall now, 2 2 moles of gas. So we want to find some way of shifting this to the right where there's more moles of gas. So in this case, in this case we're gonna want to increase the volume and that will shift it right and increase the amount of our product again. So we've been asked to look up the boiling points. So for the dick laurel ethane Are boiling point is 8347°C, which makes it a liquid at room temperature. And for a vinyl chloride, it's -134, which makes it a gas at liquid temperature. So if you look at that figure and try to replicate what's happening, we want to remove our vinyl chloride as it forms by liquefying it. Mm. So as it removed is removed, that second equilibrium is shifted to the right, which means we're using up its reactant, which means that the previous equilibrium, it's going to want to produce more product. So this causes both reactions to shift to the right and for more of your vinyl chloride. So you're going to want to remove that vinyl chloride as it forms by liquefying it.

So I am. Exchange chromatography is executed by making the reversible exchange of irons between irons present and solution on iron exchange resin. So we tend to use this to separate similar irons. And so in the first part where it's calculating the total amount of solution fed into the column 36 7.2 liters. So in part B, the expression of a volumetric flow rate for solution a be a T think was not point for liters per minute. The VA 33.6 minutes multiplied by t was able to not point not 11 90 so we can apply the mass balance in solution A M put a is equal to accumulation at a and we are able thio. The salmon that has Time T varies from not to 33.6 minutes and V A varies from zero to V a bracket. L The volume of Solution A becomes 6.72 liters on. We can calculate the amount of sodium chloride there's an A. C. L is equal to 392.72 grams and a c l. And so we can give an expression for environment for a lower rate of solution be that is tu minus no point no. 11 19 that is equal to be be dark t. So the total volume of solution a 60.48 liters total volume solution by solution be not at all number of moles of tres fad. Three points. There are two full mall on some possible potentials for error. So pumped be might have failed, causing a flow of one mole of sodium chloride to the column during the illusion period. Programs method chosen to execute in the chromatography could be incorrect. Perhaps the column was packed with the wrong reason, maybe arising. That has reduced affinity compared to the correct resin.


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