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Karina Cano Organic Chemistry Lab Report Solvent Extraction: Partition Coefficients Introduction:

The purpose of this experiment was to determine two partition coefficients of benzoic acid by separating a product from a solution mixture on a benzoic acid-dichloromethane-water mixture and benzoic aciddichloromethane-8% sodium bicarbonate mixture. The expectation of this experiment was that some compounds are more soluble in certain solvents than others. In general, likes dissolves likes, that is, polar molecules dissolve better in polar solvents and non-polar molecules in non-polar solvents. This expectation leads that the partition coefficient of benzoic acid calculated for the benzoic aciddichloromethane-water extraction would be a larger value than that of the partition coefficient of benzoic acid calculated for the benzoic acid-dichloromethane-8% sodium bicarbonate extraction. That can be attributed to preferential dissolving process of the benzoic acidwhen mixed with dichloromethane and water, benzoic acid prefers dichloromethane as a solvent. In contrast, when mixed with dichloromethane and the 8% sodium bicarbonate, benzoic acid prefers the 8% sodium bicarbonate (not dichloromethane) as a solvent. Further calculations proved these expectations of the case of the benzoic acid-dichloromethane-water extraction, and benzoic acid-dichloromethane-8% sodium bicarbonate extraction to be correct. Results: The detailed procedure on the solvent extraction is found in the Organic Chemistry Laboratory Experiments for Tulsa Community College. The result of the experiment is shown here: Part A: Benzoic acid-dichloromethane-Water Initial weight of benzoic acid (mg) Recovered benzoic acid (mg) Been in the aqueous layer (mg) 50mg 23mg 27 mg

Part B: Benzoic acid-dichloromethane-8% sodium bicarbonate Initial weight of benzoic acid (mg) Recovered benzoic acid (mg) Been in the aqueous layer (mg) 50 mg 21 mg 29 mg

Karina Cano Organic Chemistry Lab Report


Calculations Calculation of the Partition Coefficient Part A

K K
Part B

BenzoicAcid (CH 2 Cl 2 ) BenzoicAcid ( H 2 O) 27mg 1.1739 1.2 23mg

K K

BenzoicAcid (CH 2 Cl 2 ) BenzoicAcid ( Na HCO3 ) 21mg 0.7241 0.72 29mg

Discussion and Conclusions The purpose of this experiment was to calculate the partition coefficient of the given substance, benzoic acid, by placing it in a mixture of two solvents. This mixture was shaken to allow equilibrium to be established between the two phases. In this process, benzoic acid distributed itself in a way that matched its relative solubility to each of the solvents. In the case of the benzoic acid-dichloromethane-water extraction, expected to see a greater distribution of benzoic acid in the dichloromethane layer than in the water layer. This is due to the largely non-polar nature of benzoic acidwhile the carboxylic group does provide a degree of polarity. So, the water being a polar molecule does not easily dissolve benzoic acid, although expected a small amount of hydrogen bonding between the two. This hydrogen bonding allows full ionization to occurthe carboxylic group dissociates, and benzoic acid loses its acidic proton. The findings reinforced these expectations. It was calculated that 27mg, of the original 50mg, of benzoic acid dissolved in the dichloromethane layer, while only 23mg dissolved in the water layer, but there were errors in what was left of the supposed benzoic acid by the mishandle use of weighing the leftover product. Such as when not measuring the vial what was use first and had to dissolves in DCM and putting it in the sand bath again. The transferred to a vial to another vial, the benzoic acid was lost during that transferred. So, the partition coefficient was calculated to be 1.2a number that indicates benzoic acid will preferentially distribute itself in dichloromethane when added to an immiscible mixture of dichloromethane and water. The second extraction was similar to the first, except for one substitution: water was traded for 8% sodium bicarbonate. In this circumstance, we expected benzoic acid to mostly distribute itself in sodium bicarbonate. This can be explained by the fact that benzoic acid reacts readily with sodium bicarbonate

Karina Cano Organic Chemistry Lab Report


to form sodium benzoate, carbon dioxide, and water. This resultant sodium benzoate is highly ionic and thus, is insoluble in dichloromethane. The findings lead to approximately 21mg, of the original 50mg, of benzoic acid was found to have dissolved in the dichloromethane. This leads to conclude 29mg of benzoic acid dissolved in the sodium bicarbonate. Hence, in this extraction, our calculated partition coefficient of benzoic acid is 0.72. In conclusion, benzoic acid will more readily dissolve in dichloromethane than water, and will be readily dissolve in sodium bicarbonate than dichloromethane. The difference between the two different partition coefficients calculated for benzoic acid definitely point to this conclusion. References Briscoe, Bill; Miller, Toney. In Organic Chemistry Laboratory Experiments for Tulsa Community College Southeast Campus; Revised June 2010; pg.13-14. Brown, L. Theodaore; Lemay, Jr. Eugene H.; Bursten, E. Bruce; Murphy, J. Catherine. In Chemistry The Central Science; Patrick Woodward, 11th edition, 2009,534-545.