Question

A mixture containing anisole (A), benzyl alcohol (B) and aniline (C) was dissolved in chloroform. Next two extractions were performed first using HCl then with NaOH. Which of the compounds could not be separated in this procedure. Explain and show the pertinent reaction equation/s. (6 pts). How do I figure this out using structure of the compounds?

Answer 1

After dissolving the mixture in chloroform, when first extraction was done using HCl, only aniline goes into HCl because it forms anilinium hydrochloride salt which is readily soluble in water (dilute HCl solution).

When the second extraction was done using NaOH both anisole and benzylic alcohol stay in chloroform because they won't react with NaOH and thus won't dissolve in aqueous NaOH solution.