Discussion: Organic acids and bases can be separated from each other and from neutral compounds by extraction

using aqueous solution of different pH. Most organic acids are insoluble or slightly soluble in water, they are highly soluble in dilute aqueous NaOH because the organic acid will react with the base. Thus, the acid can be selectively removed from a mixture by dissolving the mixture in an organic solvent and then extracting the solution with dilute NaOH. The organic compound can be recovered from the aqueous solution by neutralization with concentrated HCl which causes precipitation and then followed by filtration to extract the precipitate. This acidbase extraction only works if the acids and bases have their large difference in solubility between their charged and their uncharged form and it cannot works if the acidic and basic functional groups in the same molecule are zwitterions, lower amines which are miscible or significantly soluble in water at most pH, very lipophilic acids and amine that do not easily dissolve in the aqueous phase in their charged form and hydrophilic acids. This experiment was carried out to determine the percentage recovery and melting point of benzoic acid and p-dichlorobenzene respectively. From the experiment, the percentage recovery of benzoic acid and p-dichlorobenzene is 90% and 61% respectively. The reason why we get the percentage recovery of p-dichlorobenzene crystals so low is because when the solution which is supposed to be heated gently was being boiled. Thus this causes some of the p-dichlorobenzene in the solution was evaporated together with water vapour and ether solution. The melting point of benzoic acid and p-dichlorobenzene is 118-122 oc and 62-67 oc respectively. Both the benzoic acid and p-dichlorobenzene are able to dissolve in the dichloromethane solution which organic compounds are soluble in organic solvent. Both solvent does not react with the dichloromethane solution, but they just dissolve in it. After that, sodium hydroxide, NaOH is added into the dichloromethane to react with benzoic acid to form sodium salt of benzoic acid and water.

Next, the sodium benzoate in aqueous layer collected in the conical flask is added with hydrochloric acid, HCl. The white precipitate is formed from the reaction.The neutralization is take place when sodium benzoate and HCl is reacted with each other to produce precipitate of benzoic acid as the main product.

The upper layer containing p-dichlorobenzene in ether is run off into a conical flask. Then, the conical flask is added with two or three boiling chips and is being heated on a hot plate to evaporate the dichloromethane. The white p-dichlorobenzene is formed in the crystal form after all the dichloromethane evaporates. The purpose of adding of calcium chloride is used to remove residual water in the organic solvent. The calcium chloride is known as drying agent in the organic solvent which are not dissolves in the solvent but drying the solvent. The purpose of adding boiling chips are, there are a lot of pores inside the boiling chips which provide cavities both to trap air and to provide spaces to allow bubbles of solvent can be form. When boiling chips are heated, it will release tiny bubbles which can prevent boiling over. Boiling over of solvent will cause loss of solution which may lead to inaccurate result to be

obtained. The boiling chips are always used when heating a solvent. The boiling chips are never added to a hot solution because it will cause immediately boiling over of solution. The precaution steps that had taken in the experiment were wearing goggle and gloves, the chemicals were handle in the fume hood and heated apparatus were handled carefully.