Assume that each of the following mixtures was added to a flask or a separatory funnel that contained diethyl ether (as an organic solvent) and mixed well. In which layer (diethyl ether or water) would the organic compound predominate in each case, and in what form would it exist (in its neutral form or as its conjugate base)?

Assume that each of the following mixtures was added to a flask or a s

1.	Assume that each of the following mixtures was added to a flask or a separatory funnel that contained diethyl ether (as an organic solvent) and mixed well. In which layer (diethyl ether or water) would the organic compound predominate in each case, and in what form would it exist (in its neutral form or as its conjugate base)?
Answer» Solution :Sodium bicarbonate will remove a proton from a carboxylic acid to FORM a water-soluble carboxylate salt, but sodium bicarbonate will not remove a proton from a typical phenol, Sodium hydroxide will remove a proton from both a carboxylic acid and a phenol to form salts in each case. Thus, in (a) benzoic acid will be found in the water layer as its sodium salt, whereas in (b) 4-methylphenol will remain in its NEUTRAL form and be found PREDOMINANTLY in the ether layer. In (C) and (d) both benzoic acid and 4-methylphenol will be found in the AQUEOUS layer as their corresponding salts.