Maria Ioakimidis Section: 021 TA: Samer Saber

Date performed: 09/12/13 Due Date: 09/19/13

Experiment 4C: Solvent Extraction II: Acid-Base Extraction Using A Two-Component Mixture of an Acid and a Neutral Substance Objective: This activity examines how solvent extraction techniques can be applied effectively to problems that require separation of mixtures of organic acids, bases, and neutral compounds. Experimental Procedure: Experiment 4C was followed as described in Mayo, pages 148-150, with the modifications listed in the Blackboard document Modifications: Instead of mixing 9-fluorenone, benzoic acid and 4- aminobenzoate all at once, only two were used. In this case, 9-fluorenone and benzoic acid was used. Instead of using 50 mg of each of the three compounds Dr. Lawlor modified it to 75mg The only melting point that was supposed to be recorded was for the 9- fluorenone and neutral compound. Reaction Scheme:

The reason 9-fluorenone (neutral compound) is not included into the equation is because during the separation step, we used only the bottom aqueous layers that contained benzoic acid and 3M NaOH that was added; the top organic layer that consisted of the neutral compound and diethyl ether was not touched in the separation process. Data and Results: 9Fluoreneone initial (mg) amount lit. mp (C) exp. mp (C) 75 NA NA Benzoic acid initial (mg) 73 Diethy l ether (mL) 4.0 3M NaOH (mL) 4.0 6M HCl (mL) NA 9Benzoic Fluoreneone acid from from aqueous organic (mg) (mg) 109 61 84 79-86 122

Observations: Both 9-Fluorenone and Benzoic acid were solids, one was yellow and the other one was white respectively. After mixing the two organic components with diethyl ether and 3 M NaOH, two phases were present. In the mixture of the organic components and the diethyl layer, the top layer was yellow, and the bottom layer was colorless. Throughout the experiment, the diethyl ether layer remained yellow. Due to time constraint, the % recover of 9-fluorenone is very high because the purified compound still contained some water or solvent. Calculations: 1) Yield of 9-fluorenone recovered from diethyl ether layer (Test tube+ Boiling stones + residue of 9-fluorenone) (Test tube + boiling stones)= (13.238-13.129)=0.109g * 1000mg/1g =109mg 2) % Recovery of 9-fluorenone Collected mass / initial mass *100% = % recovery 109/75 * 100% = 145% 3) Yield of benzoic acid recovered from aqueous layer (3 M NaOH) 0.012g * 1000mg/1g = 12mg (Benzoic acid initial benzoic acid recovered from aqueous) 73mg 12 mg = 61 4) % Recovery of Benzoic acid Collected mass/ initial mass *100% =% recovery 61/73 * 100% = 84% recovery Questions: 1. a. The organic reactant is soluble in both diethyl ether phase, and the product is more soluble in the aqueous phase. b. Benzoic acid is soluble in both because of hydrogen bonding and dipol-dipole intermolecular forces due to its compostion of carboxylic acid functional group. Diethyl ether is considered a "non-polar" solvent, and so is benzoic acid because of its benzene ring structure, so therefore it is soluble because like dissolves like. Solubility changes when Benzoic acid and NaOH were combined, it formed sodium benzoate which is soluble in water because the dipoles of water molecule attracts the sodium benzoate ions. 2. The steps omitted are similar to the ones I used in this experiment. The difference is, instead of using 3M NaOH and 6M HCL, I would of used 3M HCL and 6M NaOH. After separation, aqueous

solution would be acidic so an addition of 6M NaOH would make the solution basic and will form the precipitate. 3. Waters density is 1.00 g/ml, the top layer will consist of solvent that is less dense and the bottom layer will consist of solvent that is more dense than water. To obtain each solvents density, refer to citation #3 a) Methylene chloride will be the lower layer because its density (1.33 g/ml) is higher than water. b) Pentane will be the top layer because its density (0.626 g/ml) is smaller than water. c) Toluene will be the top layer because its density (0.87 g/ml) is smaller than water. d) Diethyl ether will be the top layer because its density (0.7184 g/ml) is smaller than water Works Cited: 1. Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep and Multiscale Syntheses, 5th ed.; John Wiley & Sons, Inc., 2011; pp 147-150. 2. Modifications for Expt 4C: Solvent Extraction II, Blackboard document. 3. Wikipedia. http://www.wikipedia.org/ (accessed 09/16/13).