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The chemical name for aspirin is acetylsalicylic acid. It is believed that the analgesic and other desirable properties of aspirin are due not to the aspirin itself but rather to the simpler compound salicylic acid, $\mathrm{C}_{6} \mathrm{H}_{4}(\mathrm{OH}) \mathrm{CO}_{2} \mathrm{H}$ that results from the breakdown of aspirin in the stomach. (FIGURE CANNOT COPY)
(a) Give approximate values for the following bond angles in the acid: (i) $\mathrm{C}-\mathrm{C}-\mathrm{C}$ in the ring; (ii) $\mathrm{O}-\mathrm{C}=\mathrm{O} ;$ (iii) either of the $\mathrm{C}-\mathrm{O}-\mathrm{H}$ angles; and (iv) $\mathbf{C}-\mathbf{C}-\mathbf{H}.$ (b) What is the hybridization of the C atoms of the ring? Of the Catom in the $-\mathrm{CO}_{2} \mathrm{H}$ group? (c) Experiment shows that $1.00 \mathrm{g}$ of the acid will dissolve in 460 mL of water. If the $\mathrm{pH}$ of this solution is 2.4 what is $K_{\mathrm{a}}$ for the acid? (d) If you have salicylic acid in your stomach, and if the pH of gastric juice is $2.0,$ calculate the percentage of salicylic acid that will be present in the stomach in the form of the salicylate ion, $\mathrm{C}_{6} \mathrm{H}_{4}(\mathrm{OH}) \mathrm{CO}_{2}^{-}$ (e) Assume you have $25.0 \mathrm{mL}$ of a $0.014 \mathrm{M}$ solution of salicylic acid and titrate it with $0.010 \mathrm{M} \mathrm{NaOH}$. What is the pH at the halfway point of the titration? What is the $\mathrm{pH}$ at the equivalence point?

This problem is what we call a back titrate Asian problem, where we add excess amount of sodium hydroxide and then determine the amount of excess. And the difference will then be the sodium hydroxide that reacted with our compound were interested in the aspirin. So to answer this question, the first thing we need to do is figure out the total moles of sodium hydroxide that we added, which will be the volume of sodium hydroxide, 50 mL or point of five leaders multiplied by its mill arat E. Then we need to subtract off the moles that didn't react with aspirin. Those air the moles of sodium hydroxide in excess that we determined with the addition of 31.96 mL, or 0.3196 liters off hydrochloric acid at a concentration of 0.29 So this is the moles of H. C. L. That was required to neutralize the excess sodium hydroxide. And because the reaction is one toe one, this is also the excess moles of sodium hydroxide. So this difference then tells us the moles of sodium hydroxide that reacted with the aspirin. So the percent aspirin is going to be the moles of aspirin, which, if we look at the stoy geometry of the reaction given for every mole of sodium hydroxide. We need two moles of sorry for every mole of aspirin. We need two moles of sodium hydroxide so we can take the moles of sodium hydroxide. We calculated and converted two moles of aspirin with the 2 to 1 relationship and then convert the moles of aspirin into grams of aspirin using the molar mass of aspirin. Divide that by the mass of the sample and multiplied by 100 to get our percent, that is aspirin. If we look at the balanced chemical reaction, we see two products. We see the fallacy laid eye on, and we see the acetate eye on those air. Both conjugate acid. Both those were both conjugate. Base is too weak acids, so they themselves are weak bases because they are basic, then the indicator that we choose needs to have a basic transition range, probably something around a transition range of eight or so. In order to determine the end point of this tie, Trish in

In question 75, you were given information about salicylic acid in a set of salicylic acid. First you're asked to determine the ph associated with a solution that is saturated. In sala silic acid. Salicylic acid has two K values. We will make the assumption that only the first K value is significant when determining the ph of the solution. A saturated solution of salicylic acid is 8.1.8 g/l. We however need a polarity. So we're going to take the 1.8 g divided by the molar mass of salicylic acid to get molds of salicylic acid And then divide that by one mole. And we get a concentration of .013 moller. The hydro knee um concentration can be estimated by taking the square root of K. A. Multiplied by the concentration That we determine 2.013 moller. However, when we do that we get 3.6 times 10 to the negative three, Which is too large. This ends up being more than 5% of the original concentration And as hopefully you learned if the hydro knee um concentration is more than 5% of the original concentration of the weak acid. Then we can't use the approximations for this equation, meaning we can't use that equation. And what we have to do is solve for the hydro knee um concentration. Using a quadratic expression or the quadratic formula. The quadratic expression that we need to use is K. A. Is going to be equal to the hydro knee um concentration squared divided by the original concentration of salicylic acid minus the hydro knee um concentration. So there's quite a bit of math that's involved. If you want to carry this all the way through, get it in the quadratic Formula format. Then used the quadratic formula and solve for the two answers. The two answers that you obtain should have one answer very similar to what we calculated up here. So calculating this number was not a waste of time. It gives us a target value so that when we use the quadratic formula we know which answer to choose. I'm not going to do all the math needless to say when I do the math I get the hydro knee um concentration equal to 3.14 times 10 to the negative three. Instead of 3.6 times 10 to the negative three. This being a better estimate of the hydro knee um concentration. So ph will then be the negative log of this hydro knee um concentration or 2.50 part B. Then is in reference to acetyl salicylic acid which is aspirin which has a smart a slightly larger K. Value. And you're asked to determine the ph for this solution at the same concentration as we determined for salicylic acid. So we'll try it again. We'll take the hydro knee um concentration and set it equal to the square root of the new K. Value, multiplied by the same concentration that we had for salicylic acid. And we get 1.97 times 10 to the -3. And still this is significantly greater than 5% of this original concentration. So again we have to use the quadratic equation So we'll set it up as K. will be equal to the hydro knee um concentration divided by the original concentration of .13 moller minus the hydro knee um concentration. I'm not going to show you all the math but if we solve this we get a hydro knee um concentration that should be very close to our 1.97 times 10 to the negative three. Or I get 1.83 times 10 to the negative three. Now, to solve for ph will simply take the negative log of the 1.83 times 10 to the negative three, and we get 2.74 2.74 as our answer.

For the given caution. We have the balance chemical equation for the reaction off aspirin with any which represented over here. Firstly, we need to calculate the moles off aspirin on moored off anyway. It's on the morning off at Seal, which is used to react the excess off hydroxide remaining in the solution. Morning off aspirin molds off any witch and moons off, etc. L. Orla, calculated by the same base since the ex SEAL, react with the excess off hydroxide, the amount off any which was consumed. So the aspirin is follow over here from balancing the equation. We know that for every two moles off base, which negative only one mole off aspirin is consumed, we let the calculate the mold off aspirin needed two moles off which over here we have the calculation representation. We need to calculate the purity off aspirin using the formula, which is represented. The purity calculated is 99.7%. Finally, for this iteration, as indicators should be used, that changes color in the range off Piquet off aspirin is three point fight, So the broom off in all blue is the indicator which we can use


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