A solution contains 1.00 g of compound A (a monoprotic carboxylic acid, molar mass 122 g mol⁻¹) and 1.50 g of compound B (a completely non-polar hydrocarbon) dissolved in 50.0 mL of diethyl ether. The partition coefficient Kd for compound A between ether and water, when A is in its non-ionized (acidic) form, is 5.0 and is defined as [A]ether/[A]water. The partition coefficient for compound B is 12.0 under all conditions. A single extraction is performed with 40.0 mL of 0.200 M NaOH(aq), which quantitatively converts compound A to its sodium salt (assumed insoluble in ether) during vigorous mixing.
(a) Calculate the number of moles of NaOH present in the aqueous phase before mixing. Determine whether this amount is sufficient to deprotonate all of compound A and justify your answer with a numerical comparison.
(b) Assuming complete deprotonation, determine the mass of compound A that will be transferred to the aqueous layer after the extraction. State any additional assumptions you make.
(c) Using the provided partition coefficient, calculate the maximum mass of compound B that will be lost to the aqueous layer during this extraction.
(d) After phase separation, the aqueous layer is acidified to pH 1 and cooled in an ice bath. Describe how compound A can be isolated in pure solid form from this layer, and outline any purification step(s) required before obtaining a final dry mass.