1 CHEM 1211 L Principles of Chemistry Lab 16 February 2004 Lab Report 1 Introduction The purpose of this project is to identify

an unknown organic acid (X) by conducting various experiments to determine the acids unique properties. By determining selected constant properties of the unknown and then comparing these properties to the constant properties of known substances, it is possible to identify an unknown substance. The properties used to identify the unknown must be intensive, or independent of amount. Both chemical properties and physical properties are intensive properties used in determining the identity of an unknown (Maserton, p. 15). Because even small amounts of impurities systematically affect observed chemical reactions, the first step to determine the identity of an unknown is to purify the substance. One technique often used to purify solids is recrystallization from a selected solvent. Because of the variable solubility of different compounds in various solvents and at various temperatures, it is possible to remove impurities by dissolving the unknown and then immediately cooling the solvent. The unknown recrystallizes, but the impurities remain dissolved in the solvent. It is then a relatively simple matter to filter the pure crystals out of the impure solvent (Lab Manual, p. 32). Once the unknown has been purified, it is possible to begin determining its constant properties. One specific physical property that is helpful in identifying an unknown is the substances melting point (Lab Manual, p. 36). Equivalent weight, the weight in grams of the acid that contains exactly one mole acidic hydrogens, is also useful when identifying an unknown

2 acid. Equivalent weight is determined by the pairing the unknowns acidic hydrogens (H+) with known quantities of hydroxyl ions (OH-) through the process of titration. Before beginning a titration of the unknown acid, several practice titrations of HCl (hydrochloric acid) with a known concentration of NaOH (sodium hydroxide) were completed to gain expertise in this experimental technique (Lab Manual, p. 37).

MISSING FROM THIS INTRODUCTION IS THE DESCRITPTION OF THE UNKNOWNS

Procedure A sample of unknown acid (#XXX) with a mass of 0.1 g was placed in a clean test tube, and 1 ml of deionized H2O was added. This mixture was heated and stirred. The unknown did not dissolve, so 1 ml deionized H2O was again added to the mixture, and the heating and stirring was continued. The unknown had not dissolved after 3 ml deionized H2O had been added, so 1 ml ethanol (25%) was added to the mixture. Heating and stirring were continued. The unknown did not dissolve at 25%, 40%, or 50% ethanol. Another sample of unknown with a mass of 0.1 g was weighed out and 1 ml 100% ethanol was added. This mixture was heated and stirred. The unknown did not dissolve, so 1 ml ethanol was again added to the mixture. A sample of the unknown with a mass of 0.1 g dissolved in 2 ml pure ethanol. A proportion was set up and solved to determine that 160 ml of ethanol would dissolve 8.0 g of the unknown. 0.1 g X ___________ 2 ml ethanol = 0.1 r = 16 8.0 g X ____________ r ml ethanol

3 r = 160 ml A sample of unknown weighing 8.000 g was placed in a beaker, and 160 ml ethanol was added. This mixture was heated and stirred until the unknown was completely dissolved. The container of dissolved unknown was placed into an ice bath and allowed to recrystallize. After the unknown was completely recrystallized, the crystals were vacuum filtered out of the solvent. The crystals were placed in a beaker with a mass of 107.359 g and covered with a watch glass. The beaker was set aside to allow the crystals to air dry completely. Some of the purified crystals remained in the solvent, so the solvent was poured into a flask and set aside to continue recrystallizing. The vacuum filtration was later repeated and more crystals were recovered. These crystals were added to the beaker and again set aside to dry. After all of the crystals were completely dry, they were weighed. The beaker containing the crystals had a mass of 112.524 g. The weight of the beaker (107.359 g) was subtracted from the weight of the same beaker containing the pure crystals (112.524 g). The actual yield was 5.165 g pure crystals. The actual yield was divided by the theoretical yield (8.000 g) and the quotient was multiplied by 100 to get a percent recovery of 64.56%. 112.524 g 107.359 g = 5.165 g pure crystals 5.165 g = 0.6456 x 100 = 64.56% 8.000 g To determine the melting point, approximately 3 mm layer X in its impure form was placed in one capillary tube. The melting point apparatus was set up. The capillary tube was placed in the apparatus and the temperature was steadily increased. As the

4 temperature neared the melting point, the rate of heating was slowed to approximately 1OC per minute. The first droplet of liquid was observed at XXXOC. All solid had disappeared at XXXOC. The melting range for the impure unknown was determined to be XXXOC XXXOC. This procedure was repeated with approximately 3 mm layer of the purified unknown. The melting range of the purified unknown was determined to be XXXOC XXXOC. For the practice titrations of HCl, 2.000 g NaOH solid was weighed out, and 500 ml deionized H2O was added to produce a NaOH solution. The reaction between the HCl and the NaOH is as follows: NaOH + HCl NaCl + H2O. A clean buret was filled with HCl solution and a second clean buret was filled with NaOH solution. The initial volume of HCl was recorded at 13.01 ml. The final volume was recorded at 20.62 ml and the initial volume was subtracted from the final volume to determine the exact volume of HCl at 7.61 ml. Exactly two drops of phenolphthalein indicator solution was added to the HCl. The initial volume of NaOH was recorded at 24.11 ml and titrated. As the solution neared the end point, the titration of NaOH was slowed to one drop at a time. The flask was shaken vigorously for as long as two minutes or until the solution became colorless. When the solution remained light pink for two minutes, the final volume NaOH was recorded at 32.61 ml. The initial volume NaOH was subtracted from the final volume NaOH to determine the exact volume NaOH at 8.50 ml. The exact volume HCl (7.61 ml) was divided by the exact volume NaOH (8.50 ml) and the quotient was multiplied by 100 to get the HCl/NaOH ratio of 0.8953. _7.61 ml HCl_ = 8.50 ml NaOH 0.8953 HCl/NaOH ratio

The table below shows three of the best of the trial titrations and their respective ratios. Trial X Volume HCl Volume NaOH Ratio HCl/NaOH 7.61 ml 8.50 ml 0.8953 Trial X 8.99 ml 10.10 ml 0.8901 Trial X 7.20ml 8.09 ml 0.8900

The percent error was found by subtracting the lowest HCl/NaOH ratio from the highest ratio. The answer was then divided by the average ratio and this answer was multiplied by 100. The calculated percent error was 0.594%. 0.8953 0.8900 0.8918 Discussion The percent recovery for the recrystallization procedure probably would have been greater if the vacuum filtration had not been done twice, because some crystals were lost each time this procedure was carried out. If the solid had been allowed to recrystallize for a longer period of time before it was filtered perhaps more crystals could have been gathered. The purified sample that was used to determine the melting point actually had an insoluable impurity in it that was not filtered out. This impurity probably lowered the melting point of the purified substance. Another melting point should have been taken for the pure unknown using another sample that did not contain impurities. MISSING FROM THE DISCUSSION IS THE BALANCED CHEMICAL EQUATION. x 100 = 0.594% error

6 The titrations of HCl and NaOH were carried out on two different days, and the ratios for one set of titrations were approximately half of the ratios from the day before. This difference may have been because a different container of HCl was used the second day. If the concentration HCl was different, it could have caused this difference in ratios. The percent error could have been caused by settling of the NaOH, by a buret that was not perfectly clean, or possibly by misreading of the meniscus. There may have been other unknown factors that caused the percent error to be too large. Conclusion In this set of experiments, the unknown acid has been purified by process of recrystallization with a 64.56% yield. The melting range has been determined for the unknown in its impure form (238OC 241OC) and in its pure form (240 OC 241OC). Several practice titrations of HCl with NaOH have been conducted with a 0.594% error. The information gathered through the process of these experiments will be used to help identify the unknown acid.

Works Cited Maserton, William L. and Cecile N. Hurley. Chemistry: Principles and Reactions, 5th ed. Thomson Learning, Inc., Toronto, 2004.

7 The Identification of an Organic Acid, 3rd ed. Georgia State University, Atlanta, 1992.