Toluic acid, naphthalene and sodium chloride are present in a solid mixture. Pro

Question

Toluic acid, naphthalene and sodium chloride are present in a solid mixture. Propose a detail separation scheme to isolate these three compounds as solids. Below is a list of reagents available in lab. You may use any of these given reagents (e.g., acids, bases) as needed in your separation scheme and you also have access to a solvent evaporator if a solvent must be evaporated, and a filtration apparatus to filter. Be specific in each reagent name and technique used in your separation scheme. The most efficient separation scheme will receive the most credit.

Explanation / Answer

5. Separation of toluic acid, naphthalene and sodium chloride

1) Add water + diethylether to the mixture

(a) sodium chloride dissolves in water and can be separated from the other two. Evaporation of water would give NaCl back.

2) The ether layer is treated with 5% aqueous NaHCO3 solution.

(a) Toluic acid reacts and forms sodium salt which is water soluble and is separated out from ether layer.

(b) Add ether to the aqueous layer and acidify with 6 M HCl to isolate toluic acid from solution.

(c) Separate ether layer and add anhydrous MgSO4 and filter the solution, discard the residue.

(d) evaporate ether to isolate toluic acid.

3) Ether layer now has naphthalene.

(a) Add anhydrous MgSO4 to ether layer, filter

(b) discard residue, evaporate ether to get naphthalene back.

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