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TITLE OF EXPERIMENT: EXTRACTION WITH ACID AND ALKALINE
OBJECTIVES:
1) Performed on acid-alkaline extraction 2) Learned to recovered benzoic acid and p-dichlorobenzene from its mixture using acid-alkaline extraction method 3) Determine the percent recovery of benzoic acid and p-dichlorobenzene 4) Determine the melting point of recovered benzoic acid and p-dichlorobenzene
INTRODUCTION:
Extraction involves dissolving a compound or compounds either from a solid into a liqiud or from a solution into another liquid. An acid-alkaline extraction is also known as a form of liquid-liquid extraction. Extraction is a procedure to separate compounds based on their relative solubility in two different immiscible solutions. Two layers are formed when the mixture are separated. The upper layer contains a low dense solvent. Basically in most of the extraction, one of the solvent used would be water as an aqueous solution and the other would be an organic solvent that is insoluble in water. The choice of organic solvent must be volatile so it can easily by removed by evaporation when forming crystals.
The cleanest separations of organic compounds can be performed by using acid or alkaline solutions which can convert the compound to be extracted to a water-soluble and ether insoluble salt. Phenolic compounds undergo similar salt formation with sodium hydroxide solution. Hence, sodium hydroxide solution can be used to extract a carboxylic acid or phenolic compound from its solution in an organic solvent. To remove the organic impurities from a carboxylic acid or phenol, dissolved in aqueous sodium hydroxide, organic solvents can be used. Aqueous solutions of sodium bicarbonate can convert carboxylic acids to their sodium salts but are not sufficiently alkaline to form salts of phenolic compounds. That’s why this method can be used for the separation of a carboxylic acid and a phenolic compound. Firstly, remove the acid from solution in an organic solvent by using extraction with sodium bicarbonate and then removed the phenol with sodium hydroxide solution. Inorganic acids are regularly removed from organic solvents by extraction with sodium carbonate, sodium hydroxide, or sodium carbonate solutions. Dilute hydrochloric acid is used to extract basic substances from mixtures or to remove the basic impurities. The dilute acid converts the base such as ammonia or an organic amine (R3N) into the water-soluble chloride salt (R3NH+, C־ ) Organic impurities can be removed from amine by using the dilute acid solution with organic solvent to extract it.
Sodium salts of carboxylic acids and phenolic compounds are readily reconverted to the parent compounds by treatment with sulphuric or phosphoric acid. The chlorides of amines revert to the original amine upon addition of sodium hydroxide solution.

CHEMICAL/REAGENT: (i) Benzoic acid (ii) P-dichlorobenzene mixture (2g) (iii) Ether solution 40ml (iv) 5ml portion of cold distilled water (v) Anhydrous CaCI2 (3 or 4 granules) (vi) Water 30ml (vii) Concentrated HCI
EQUIPMENTS:
(i) Separotory funnel (250ml) (ii) Stopper (iii) Conical flask (iv) Hot plate (v) Tarred watch glass (vi) Buchner funnel (vii) Filter paper (viii) Litmus paper

PROCEDURE: 1) 1 g of benzoic acid and 1 g of p-dichlorobenzene are prepared in 40 ml of ether in a beaker. 2) The ether solution is poured into a small separatory funnel followed by 20 ml of 10% NaOH solution. 3) The funnel is stoppered and is shaked well by inverting occationally and releasing any surplus pressure through the tap and it is allowed to stand. 4) The stopper is removed and the lower aqueous layer into a conical flask. 5) The residue is shaked in the with another portion of 10ml 10% NaOH and the lower layer is run off into the same beaker. 6) The solution in beaker is added with conc. HCl until the solution become acidic. 7) The ether solution is washed with 30ml of water and run off the lower layer to be discarded. 8) The ether solution is added with three anhydrous CaCl2 and the mixture is shaked occasionally until no turbidity remain. 9) The ether soution is decanted into clean dry small conical and two boiling chips are added. 10) Then beaker is heated until approximately 10ml of ether remains. 11) The ether solution is left it at fume hood to evaporate. Meanwhile, the precipitated benzoic acid is filtered by using Buchner funnel and flask. 12) The benzoic acid is washed with 5ml of cold distiled water and ensures the crystals are completely dry by pressing in a folded paper. 13) The weight and melting point of recovered benzoic acid and p-dichlorobenzene is determined.

RESULTS:
Weight of benzoic acid= 1g
Weight of p-dichlorobenzene= 1g
Weight of filter paper of benzoic acid=0.5363g
Weight of filter paper of p-dichlorobenzene= 0.3326g
Weight of two filter paper + weight of benzoic acid recovered = 1.4982g
Weight of two filter paper + weight of p-dichlorobenzene recovered = 1.2950g
Weight of benzoic acid recovered = 0.9619g
Weight of p-dichlorobenzene = 0.9624g
Melting point of benzoic acid = 122 C
Melting point of p-dichlorobenzene = 52 C
CALCULATIONS:
a) Percent recovery of benzoic acid:
=weight of benzoic acid recovered ÷ weight of benzoic acid started with × 100%
=0.9619g ÷ 1g
=96.19%
b) Relative melting point of benzoic acid:
= melting point of compound recovered ÷ melting of pure compound × 100%
=122.0 C ÷1222.4 C ×100%
=99.67%

c) Percent recovery of p-dichlorobenzene:
=weight of benzoic acid recovered ÷ weight of benzoic acid started with × 100%
=0.9624g ÷ 1g
=96.24%

d) Relative melting point of p-dichlorobenzene:
= melting point of compound recovered ÷ melting of pure compound × 100%
=52.0 C ÷ 53.0 C ×100%
=98.11%

DISCUSSION:
The important aspects when choosing a solvent system for extraction is to pick out two immiscible solvents. Some common liquid/liquid extraction solvent pairs are water-dichloromethane, water-ether and water-hexane. In this experiment, the benzoic acid (1g) and p-dichlorobenzene (1g) is used to dissolve in ether, (C2H5)2O. Most extraction includes water because it is highly polar and immiscible with most organic solvents. In addition, the compound that is attempted to be extracted must be soluble in organic solvent but not soluble in water. The volatility of the solvent is very important. This is because solvent have low boiling point like ether which can used to dry the isolated material very fast since the boiling point of ether is very low.
The benzoic acid and p-dichlorobenzene are able to dissolve in ether solution. Both solvents doesn’t show any reaction with the ether solution, but will dissolve in it. After that, freshly prepared sodium hydroxide, 10ml NaOH is added into the ether to react with benzoic acid to form sodium salt of benzoic acid and water.

The funnel is closed with a stopper and then shaken well, occasionally inverted and releasing any surplus pressure through the tap. The reaction between benzoic acid and sodium hydroxide produces a lot of vapor after a few times of shaking so that’s why there is surplus pressure produced from the reaction have to be released through the tap of the separator funnel several times to reduce the pressure inside it. After that two layers of solution are formed; the upper layer is organic solvent while the lower layer is aqueous layer. It is allowed to stand for a while and then the stopper of the separating funnel is removed. The sodium salt of benzoic acid which is dissolved in the aqueous layer are runs off into a beaker. The addition of NaOH for a second time into the solvent is used to make sure that all the benzoic acid are reacted completely with sodium hydroxide. This reaction causes the similar two layers. The aqueous layer is transferred into the same beaker by using the same procedure. CaCl2(s) + H2O(l) à CaCl2. H2O(s) |
30ml of Water is added into the separatory funnel to wash the ether solution. Then, the granular calcium chloride is added into the organic solvent after run off and the aqueous layer is discarded. The purpose of adding of calcium chloride (CaCI2) is to remove residual water in the organic solvent. The CaCI2 in the granular form will be preferable. The CaCI2 is known as drying agent in the organic solvent which does not dissolves in the solvent but only dry the solvent. The CaCI2 clump together with the water droplets as it solidifies. In simple words, the calcium chloride (CaCI2) reacts with water to form hydrates which is their preferred form when water is available. The chemical reaction between granular calcium chloride and water is;

When a bigger size of hydrate is formed in the solvent, the heavier hydrate sinks to the bottom of the funnel and so it can be easily removed. An excess drying agent should be used to ensure that all the water in the solvent is removed. If the water remains in the materials collected, it could interfere with the analysis.
The organic layer containing p-dichlorobenzene in ether, which is run off into a beaker. Then, the beaker is added with two or three boiling chips and is heated on a hot plate to evaporate the ether. The boiling chips are small, insoluble, and porous stones made of calcium carbonate or silicon carbide. There are a lot of pores inside the boiling chips which provide cavities both to trap air and to provide spaces to allow bubbles to form. When boiling chips are heated, it will release tiny bubbles which can prevent boiling over. Boiling over of solvent will cause lost of solution which may lead to inaccurate result to be determined. The boiling chips are always used when heating a solvent. The boiling chips should never be added to a hot solution because it will cause immediate boiling over of the solution. If the ether in the beaker is left 20ml, the solution is left aside in the fume hood. The ether is not continuously to be heated because the crystal of p-dichlorobenzene will melt and hence the crystal cannot be recovered. The white p-dichlorobenzene is formed after all the ether evaporates. The weight of recovered p-dichlorobenzene is about 0.9624g with melting point of 52 C . In addition, the percent recovery and relative accuracy of melting point for p-dichlorobenzene are 96.24% and 98.11%. The percent recovery of p-dichlorobenzene is not 100% which may be due to the lost of product in the experiment. Furthermore, the relative accuracy of melting point is less than 100%.
In the next method, Sodium benzoate in aqueous layer which is collected in the beaker is added with hydrochloric acid, HCl. The white precipitate is formed from the reaction. Litmus paper turns from blue to red colour when excess HCl is added. The neutralization takes place when sodium benzoate and HCl react with each other to produce precipitate of benzoic acid as the main product (sodium chloride salt and water are the side product).

The neutralization process between sodium benzoate and HCl:

The white precipitate is washed with 5ml portion of cold distilled water during filtration to minimize the solubility of benzoic acid in the water. After the filtration the white precipitate is dried by pressing with a folded filter paper and finally the benzoic acid crystal is obtained. The weight of benzoic acid recovered and its melting point are 0.9619g and 122 C. The percent recovery of benzoic acid is 96.19% while the relative accuracy of melting point of benzoic acid is 99.67%. Similarly, there is a percent loss of the product during conducting the experiment. Most probably some the products are dissolved in the cold distilled water during the filtration.
During the experiment make sure to avoid getting near the flame during the separation because ether is highly flammable and we should wear gloves when handling the concentrated HCl. More prefer to use heat resistance gloves when handling with the heated solution. Please make sure that evaporation process must be performed in the fume hood.

CONCLUSION:
From the experiment conducted, we are able to extract 96.19% of the benzoic acid and 96.24% of p-dichlorobenzene. The melting point of benzoic acid and p-dichlorobenzene that we got from the experiment are 122 ºC and 52 ºC respectively. These two melting points show some degree of deviation from the theoretical value. This is because the extracted crystals are not 100% pure. The relative accuracy of melting point of benzoic acid and p-dichlorobenzene obtained from this experiment are 99.67% and 98.11% respectively.
REFERENCE:
1) Koh, S. (2012). Introduction to Extraction of Acid and Alkaline.
Available: http://www.scribd.com/doc/97554752/Experiment-11.
Last accessed 18th March 2013.

2) Goh, K. (2011). Discussion about the Extraction of Acid and Alkaline.
Available:http://1chemistry.blogspot.com/2011/09/extraction-with-acid-and-alkaline.html. Last accessed 18th March 2013.

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...Cp8, Coordination Compound, Synthesis & Product Yield Observation, Description & Questions 1. Compound 1 was initially a light blue color. After adding the oxalic acid and heating it changed to a yellow color. Once the saturated potassium oxalate solution was added it changed to a red color. Once most of the hydrogen peroxide was added it changed colors again to murky brown. Finally it changed to a green color after the solution was brought to a boil and more oxalic acid was added. Compound 3 were crystals that of the same green color. 2. We started with: 10.000 g Fe(NH4)2(SO4)2 • 6 H2O / 392.14 g/mol = .02550 mol. We ended with 6.557 g K3Fe(C2O4)3 • 3 H2O / 491.24 g/mol = .01335 mol. .01335 mol / .02550 mol * 100% = 52.35% yield. 3. If the yield had been greater than 100% percent the likely reason would be that some liquid from the washing process hadn’t been allowed enough time to dry and caused the final weight measurement to be off. 4. Since the yield of the final solid crystals was about half of the starting amount it is likely because the solution didn’t have enough time to completely form into the solid compound. Also, in there may have been a limiting reagent that wasn’t taken into consideration. 5. Charge on iron in reagent I (Fe(NH4)2(SO4)2 • 6 H2O) = 2+ 6. Charge on iron in product III (K3Fe(C2O4)3 • 3 H2O) = 3+ 7. K3Fe(C2O4)3 • 3 H2O = potassium trioxalatoferrate(III)...

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...eChat Reflection Sheet Name: Brittany Date: October 5th eChat Activity #: 1.3.1 Answer the following questions and submit your summary after attending the eChat: 1.What topics were discussed during this eChat? We began this eChat with a quick look at the calender and important dates that are fast approaching, such as the test. This test will be written on Wednesday, October 21st. We have approximately two weeks to catch up on work and prepare ourselves for the test date. You will be emailing us to confirm we set up a time with our contact teacher for the 21st to write the test. The test is a paper copy and you will be providing us with a formula sheet, periodic table and the polyatomic ion sheet. We are not permitted to bring any materials with us to the written test as everything will be provided. I appreciate the fact that you will be emailing us to let us know which formulas we must study and ensuring that we memorize the prefixes for the covalent compound naming. We reviewed a few examples for balancing equations practice and discussed using the lowest coefficient possible as well as following proper convention for symbols. We moved on to reviewing an example for writing word equations as well as percent composition. During the percent composition you ensured we understand each step must be included for full point in case of an error during our procedure. We finished the eChat reviewing empirical formulas as well molecular formulas and discussing stoichiometry...

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