4) You have to separate 4-toluic acid (a strong acid, pKa 4.36 - look up structure) from 4-bromoaniline (a base - look up structure). Assume the two substances don't react with each other. The mixture of 4-toluic acid and 4-bromoaniline is dissolved in ether. You MAY 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) Why would using either sodium bicarbonate or sodium hydroxide be able to extract 4-toluic acid into the aqueous layer? (Give reasons for both)

b) What would the name of the species in the aqueous layer be when the mixture mentioned above is extracted with either sodium hydroxide or sodium bicarbonate?

c) If you react the mixture above with aqueous HCl first, why would it only extract the 4-bromoaniline into the aqueous layer?