Description 1) Ibuprofen has a carboxylic acid functionality and has a pKa of 4.43. Aspirin has a c ...

---

Description 1) Ibuprofen has a carboxylic acid functionality and has a pKa of 4.43. Aspirin has a carboxylic acid functionality and has a pKa of 3.50. Acetaminophen has a phenol functionality and has a pKa of 9.51. You will need the following information: The pKa of HCl is –7; pKa of carbonic acid is 6.52 and the pKa of water is 15.  a) You have a mixture of ibuprofen and aspirin that you wish to separate by extraction. The mixture is dissolved in methylene chloride. Would reacting the mixture with an aqueous solution of NaOH separate one substance from the other? Why or why not?  b) You have a mixture of ibuprofen and acetaminophen that you wish to separate by extraction. The mixture is dissolved in methylene chloride.  i) Which among HCl, sodium bicarbonate and sodium hydroxide solutions would you use to separate the two substances?  ii) Why can you not use the other two options from above to effect the separation (explain what would happen if you did).