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Solubility and Extraction Techniques

This document discusses extraction problems involving benzoic acid, toluene, aniline, and aspirin/salicylic acid. It provides solubility data and asks the reader to: 1) Calculate the Ka for benzoic acid and the partition coefficient for extracting it from a water-CCL4 mixture. 2) Design an extraction process to separate a mixture of benzoic acid and toluene dissolved in CCL4. 3) Calculate the Kb for aniline using its solubility and pH data, and explain how to separate a mixture of toluene and aniline using ether extraction. 4) Calculate the partition constants for aspirin and salicylic

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93 views1 page

Solubility and Extraction Techniques

This document discusses extraction problems involving benzoic acid, toluene, aniline, and aspirin/salicylic acid. It provides solubility data and asks the reader to: 1) Calculate the Ka for benzoic acid and the partition coefficient for extracting it from a water-CCL4 mixture. 2) Design an extraction process to separate a mixture of benzoic acid and toluene dissolved in CCL4. 3) Calculate the Kb for aniline using its solubility and pH data, and explain how to separate a mixture of toluene and aniline using ether extraction. 4) Calculate the partition constants for aspirin and salicylic

Uploaded by

diRkdARyL
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as DOC, PDF, TXT or read online on Scribd

Chemistry 14CL Extraction Problems

Winter 2009

1. The solubility of benzoic acid in water is 3.4 g/L; in carbon tetrachloride it is 33.3 g/L. The pH of a saturated solution of benzoic acid in water is 2.8. (a) Calculate the Ka for benzoic acid. (b) Calculate the partition coefficient for benzoic acid in a water-CCL4 solvent pair. (c) What weight of benzoic acid would be transferred to an aqueous phase if 1 g of benzoic acid were dissolved in 100 mL of carbon tetrachloride and the solution were extracted with 100 mL of water? (d) The solubility of benzoic acid in a 0.1-M solution of NaOH is 12.2 g/L. Explain why this is so much larger than the solubility in water. (e) Toluene has a solubility in water of 0.67g/L; it is miscible with carbon tetrachloride. Draw a flow chart to show how you could use extraction to separate a mixture of 0.3 g each of benzoic acid and toluene in 100 mL of carbon tetrachloride. Calculate the amount of each compound remaining in the carbon tetrachloride after one extraction based on your design. 2. The solubility of aniline in water is 35.0 g/L; it is miscible in both ether and carbon tetrachloride. (a) The pH of a saturated solution of aniline in water is 9.3. Calculate the Kb for aniline. (b) Explain how you could separate an equimolar mixture of toluene and aniline from ether. 3. The partition coefficient for an organic solute A distributed between ether and water is 5.0. That is, K (ether/water) = 5.0 (a) If 10.0 g of A were dissolved in 100 mL of water, what weight of A would be removed by a single extraction with 100 mL of ether? (b) What weight of A would be extracted by two sequential extractions of the water with 50 ml of ether for each extraction? 4. The Merck Index gives the following data for the solubility for 1 g of aspirin or salicylic acid. Aspirin (acetylsalicylic acid) 300 mL of H2O 17 mL of chloroform 12 mL of ethyl ether Salicylic acid 460 mL of H2O 42 mL of chloroform 3 mL of ethyl ether

(a) Calculate the partition constants, K(chloroform/H2O) and K(ether/H2O), for aspirin and for salicylic acid. (Hint: First convert from (volume solvent)/g compound to (g compound)/100 mL solvent .) (b) If you had a mixture of equal weights of aspirin and salicylic acid in an aqueous phase, which solvent pair (ether-water) or (chloroform-water) would give the best separation of the compounds. Why?

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