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The extraction method can be done easily when particular solute will form an equilibrium distribution between two immiscible phases at least one of which is usually a liquid. Immiscible is a term that indicates two phases which do not dissolve in each other. Two different layers can be seen clearly in solution. By using the extraction, the organic compound can be removed from a solution. Besides that, the same process of extraction can be used to wash solution of an organic solute in an organic solvent without the present of organic impurities. Extraction is accomplished by shaking a solution in a separatory funnel with a solvent that is immiscible with the solvent. From that, the desired substance is already dissolved because the desired substance is more soluble. Two liquid layers are formed which can be separated from each other by draining the lower layer through the stopcock of the separatory funnel. For example, a reaction is carried out in an aqueous solution and the desired product is an organic compound. This reaction mixture is then shaken with a small amount of an organic solvent such as ether where the organic solute is more soluble in the organic solvent than in water. After this, the undesired aqueous layer is drawn off and discarded. The remaining organic solution is shaken with a small amount of distilled water to wash the organic solution in order to remove inorganic impurities such as salts. The new aqueous layer that is formed then contains the inorganic impurities. This aqueous solution is then also drawn off and discarded. Th e organic solution that remains which should contain the bulk of the organic solute is now ready for further treatment to isolate the wanted product. Some of the organic solvents that are commonly used for extracting aqueous solutions include diethyl ether, dichloromethane (methylene chloride), trichloromethane (chloroform), tetrachloro -methane (carbon tetrachloride), pentane, hexane, cyclohexane, heptane, octane, benzene, toluene, petroleum ether and ligroin. While the other liquids are pure substances, petroleum ether and ligroin are mixtures of hydrocarbons. In summary, in order to choose a solvent to extract a non polar solute from water, the solvent: a) should be immiscible with water b) should be a better solvent for the substance that are desired to extract than water c) should be volatile enough that it can easily be removed from the desired
substance d) should be nontoxic or has relatively low toxicity e) should not react with the substance being e xtracted .
The mixture was let stand to allow the layers to separate. 6M HCl was added into each Erlenmeyer flasks while stirring until the solution was acidic. 4. Another 5mL of 1M NaOH solution was added to the ether layer in the funnel and step 1 to 3 were repeated for the second extraction step. The pressure was vented by tilting the funnel and opening of the stop cork. The solution was transferred to the separatory funnel and 5mL of 1M NaOH was added. Then they were placed in a test tube. 0. The aqueous layer solution was drained to another Erlenmeyer flask and it was labelled as second extraction NaOH.12g benzoic acid were weighed. 10mL of ether was added to the mixture and the test tube was shaken to dissolve the mixture. 2. The aqueous layer was drained into an Erlenmeyer flask and it was labelled as first extraction NaOH.24g of unknown sample and 0. Extraction and washing 1. The flasks and some water were cooled in an ice bath for 15 minutes. This was done in the fume hood. 2. 3.The reactions that occur in the extraction are as following: Experimental procedures Neutralization and acidification 1. . The funnel was capped tightly and the layers were mixed by swirling and shaking gently for 30 seconds. Vacuum filtration / separation 1.
Drying / use of drying agent for organic solution / evaporating 1.1264 0. The dried ether layer was transferred to the beaker by using a clean Pasteur filter pipette. 2. The funnel was capped. mixed.0950 -\ Unknown sample 0. The Erlenmeyer flask was washed with the chilled water and the suction was allowed for 5 minutes to get the solid dry. The aqueous layer was discarded. 5mL of saturated solution of NaCl was added to the ether layer in the separatory funnel. The solid benzoic acid was weighed and its melting point was obtained. 3. 3. Result and Observation Description Actual weight (grams) Weight that is recovered (grams) Observed melting point ( C) Benzoic acid 0. 2. The percent recovery was calculated and the sample was turn ed in. 4.2. The unknown neutral compound was determined by comparing it with the two chemicals given. Small amount of the solid was scraped out and its melting point was obtained. . It was gently scraped into a watch glass and the drying process was completed in the oven. Melting point determination 1. vented and the layers were let to separate. It was reweighed to determine the yield of th e unknown sample.2353 163. White precipitate of unknown sample is formed. The sample was turn ed in. it was swirled and let stand for 10 minutes.2464 0. The ether layer was transferred into an Erlenmeyer flask and 1g of anhydrous Na2SO4 was added into the flask. 3. The solid benzoic acid was collected by using a Buchner funnel and filter flask. The percent recovery was calculated. The beaker containing solid ether was cooled at room temperature and it was dried.0 White precipitate of benzoic acid is formed. The ether was evaporated carefully in the steam bath in the fume hood. The flask was corked. A small beaker was weighed.
For benzoic acid. the unknown sample is triphenylmethanol since it has same melting point. the mass of benzoic acid and unknown sample are 0. After the procedure was ended. For the unknown solution. The pressu re inside the funnel is quite low so that the solid is not dry enough even the suction was allowed to continue for about 5 minutes.50 % Discussion In the experiment. the heat ma y influence the reading of analytical balance.2464 g = 95. the solid benzoic acid may not scrape out completely. Besides that. However. the pressure inside the funnel is released out by opening the stopcock for few seconds. the melting point between the unknown sample and the given compound is compared.1264 g = 75. some steps are taken in order to get good result of experiment.2464 g respectively.50 % respectively.Calculations Percent recovery for benzoic acid: = 0. Thus. When the separatory funnel was shaken. some errors may occur so that 100% of substances is not achieved. It is important because it is needed to calculate the percent recovery later. From the calculation.16 % Percent recovery for unknown sample: = 0. the weight of both benzoic acid and the unknown is measured. the beaker containing the unknown sample was heated in the hot water bath or steam bath.1264 g and 0. the mel ting point of the unknown sample is determined. the solid was f iltered by the vacuum filtration. Next. it may not cool down enough. This will affect the reading of final mass of benzoic acid. As for both sample. Then. when the aqueous layer is discarded from the . the mass of benzoic acid and unknown sample were reweighed. When the beaker was reweighed. the percent recovery for benzoic acid and unknown sample are 75. At the beginning of the experiment. Hence.0950 g X 100% 0.2353 g X 100% 0. It seems like both sample has high percentage even though the pure products are not formed. There is maybe some solid benzoic left on the filter pap er. Thus. The temperature is 163.0 C.16 % and 95. the mixture in the funnel is ensured to be mixed well so that the complete separation is occurring and the products are not contaminated. From that. Apart from that. the mixture of benzoic acid and an unknown sample were extracted in order to determine the identity of that unknown sample.
Conclusion The mixture can be separated by using separatory funnel. .ppt http://www. 3. Percent recovery for benzoic acid is 75. Prentice -Hall. The melting point of an unknown is 163 .doc Paula Yurkanis Bruice.edu/~jgiles/138 Labs/138 Lab 10. Inc. List four water-immiscible liquids other than ether that could be used to extract organic compounds from aqueous solution.16 % while for the unknown sample. it is ensured that the stopcock is comp letely closed at the boundary of the immiscible solution. References http://faculty.pdf http://www. Organic Chemistry (3 rd edition).maricopa.umass. percent recovery is 95. 2001.Tetrachloromethane .chem.Chloroform . Thus. Thus. the moisture from the air may trap in the bottle.0 C..swosu. Draw the structure of the product when benzoic acid reacts with sodium hydroxide. If we open the bottle.Dichloromethane . the ether layer will not flow into the aqueous solution. the unknown sample is triphenylmethanol. Why is the product of this reaction easily extracted into H 2O while the original benzoic acid is not so easily extracted into H 2O? . Why is it wrong to leave a bottle of anhydrous sodium sulphate or calcium chloride open? It is because of the air containing water vapour.50 %.edu/~samal/269/extract.kelly/extract_pl.Hexane 2.mc.separatory funnel. Questions 1.edu/william.
it cannot be extracted into water. However. Thus. 4.Sodium benzoate is a water soluble compound. the pure benzoic acid can be produced. Develop a procedure for isolating a neutral compound from mixture containing a basic impurity by drawing a flow chart as on page 20. . the pure benzoic acid is not soluble in the water. Why does benzoic acid precipitate out when the aqueous layer is acidified with HCl? When sodium benzoate was reacted with hydrochloric acid. Benzoic acid will form in solid state. It can be extracted into water. Benzoic acid is non soluble in water. 5.
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