5. You are given a mixture A in dichloromethane (DCM) as solvent, containing equal proportions of naphthalene, benzoic acid, aniline and 2-naphthol. The structures and some physical properties of the compounds are given as table. Compound pKa mp (C) bp (C) Naphthalene 80-82 218 From this mixture aniline and benzoic acid were separated. You are required to separate the remained two components of this mixture. Benzoic acid 4.2 122-125 249 2-Naphthol 9.5 120-122 Benzaldehyde 285-286 a) Draw a flow chart for the separation. Indicate organic, water phases location as 178.1 upper or bottom layers. (10 p) -26 b) What would you do if there is benzaldehyde in your starting mixture at the very beginning of the process. (5 p)