Identification of a Unknown Acid Introduction Every chemical, in its purest form, has been created or formed naturally has

a set of properties that define them. The purpose of this lab was to find out the identity of an unknown acid by using these properties. I was give the acid with the identification number of 6680021-FF11. The acids that we were given were con taminated with some kind of impurity and we had to first purify it by the method of recrystallization, because the impurity can alter the properties of the acid if not removed. Then we determined the melting point by using the Bibby-Sterlin device. After that, we used titration methods to find out the equivalent weight of the recrystallized acid. Then we did a computer search with the information that we found to narrow the possible identity of the acid down to at least 3 to 5 acids. Based on these results we had to find the pKa of the acid by doing pKa titrations and finally if we had to perform sodium fusion. Results Melting Point Determination Procedure: 1.) Fill from 2 to 4 mm of crude acid in capillary tube. 2.) Place the capillary tube in one end of the Bibby-Sterilin device 3.) When it reaches 95 degrees, press start again. 4.) Watch the acid to see if it starts melting. 5.) Record the range of the temperature (when it first started melting to co mpletely melted). 6.) Repeat steps 1-6 with the recrystallized acid and the standard that fits the range of your recrystallized acid. Data: While watching my crude acid melt, I had to keep increasing my plateau tem perature ( the temperature that you input before you press start) because the te mperature was not high enough for it to start melting. My recrystallized acid st arted melting at 167 and didn t finish until 178 degrees. My crude did not even melt until 200 degrees. NaOH Standardization Purpose: The purpose of doing the NaOH standardization is for its data to be used in the titration of the weight of the unknown acid, using phenophatlien as an indicator . By using the concentration this NaOH solution, the weight of the unknown acid that was titrated, and the volume of NaOH that was used to titrate it, we can de termine the weight of the unknown acid. Procedure: 1.) Weigh 0.3 to 0.4 of KHP using the analytical balance. Record the weight of the sample up to 4 decimal places. 2.) Transfer the sample to a clean Erlenmeyer flask. Make sure you rinse the weigh boat with the water bottle filled with deionized water and the mouth and sides of the flask to get all of your sample. 3.) Add 50 mL of deionized water to completely dissolve the KHP crystals, if needed, heat up on hot plate. 4.) After dissolving the crystals, cool to room temperature, add one drop of phenolphatlein indicator to the flask and titrate with NaOH solution until the contents of the flask turns pink. 5.) Record initial and final reading of the buret. Make sure to use two deci mal places. 6.) Repeat steps 1-5 two more times. Data: Amount of KHP (g) Volume Before Titration (mL) Total Volume Titrated (m L) 0.4069 g 50 20.7 0.46 g 50 28.7 0.3252 g 50 34.5 Equivalent Weight Titration Procedure:

1.) Weigh 0.3 to 0.4 of unknown using the analytical balance. Record the wei ght of the sample up to 4 decimal places. 2.) Transfer the sample to a clean Erlenmeyer flask. Make sure you rinse the weigh boat with the water bottle filled with deionized water and the mouth and sides of the flask to get all of your sample. 3.) Add 50 mL of your recrystallization solution to completely dissolve the unknown crystals, if needed, heat up on hot plate. 4.) After dissolving the crystals, cool to room temperature, add one drop of phenolphatlein indicator to the flask and titrate with NaOH solution until the contents of the flask turns pink. 5.) Record initial and final reading of the buret. Make sure to use two deci mal places. 6.) Repeat steps 1-5 3 more times. *Data: (*Due to contamination ) Weight of Unknown Acid L) 0.321 g 0.3093 g of NaOH, I had to make another solution and titrate twice (g) 50 50 Initial Volume (mL) 18.5 18.4 Total Volume Titrated (m

pKa Titration Procedure: 1.) Using a analytical balance, weigh out 0.2 of the recrystallized unknown acid directly into a clean, dried 250 mL beaker 2.) Place the spinning bar in the beaker 3.) Dissolve the acid by using your appropriate solvent ( one used for recry stallization). 4.) For the first determination, add 50 mL of ethanol to the beaker by a bur et until it is completely dissolved. 5.) Heat up on a hot plate until it is dissolved, then add 50 mL of water. 6.) Cool to room temperature. 7.) Rinse the buret with 5 mL portions of NaOH solution. 8.) Fill buret up to the 0.0 mark. 9.) Ask for a pH meter and ask your TA to help you calibrate it. 10.) Record the initial pH of the unknown solution and keep the electrode ins ide of the solution throughout the whole experiment. 11.) Begin adding NaOH to the solution one mL at a time, stopping to measure pH of the solution of each addition. 12.) When the end point is below 1mL of the expected end point, add no more t han 0.2 mL of NaOH at a time for a total of 2 mL until the pH has stabilized. Data: Volume Titrated (mL) pH 0 3.1 1 3.69 2 4.05 3 4.16 4 4.25 5 4.34 6 4.35 6.2 4.37 6.4 4.39 6.8 4.4 7 4.44 7.2 4.46 7.4 4.47 7.6 4.48 7.8 4.49

8 9 10 11 12 13 14 15

4.54 4.7 5.06 5.7 12.07 12.5 12.68 12.7

Sodium Fusion* *Due to the computer search, one of the acids that could possibly be my unknown contained Chlorine, a halogen Halogen Test Procedure: 1.) Acidify (test pH with litmus paper) 2mL of the filrate that was made by either your instructor or TA s with dilute nitric acid. 2.) Add a few drops of silver nitrate to the filtrate. 3.) Observe the solution to see if it forms a white or pale yellow precipita te then rapidly darkens when exposed to light which states the presence of a hal ogen. Data: As I observed the test tube, I saw the milkfish yellow precipitate and on the bottom of the tube I saw the black precipitate that it formed. Conclusion Based on all of the experiments that I have completed, I have come to the conclu sion that my acid is 5-chloro 2-hydroxybenzoic acid or ClC6H3(OH)COOH. The melti ng point of the recrystallized acid came up to be in the range of 167- 175,this helped me narrow the identity to two acids, the one I mentioned above and 4-tert -butylbenzoic acid. This acid s melting point is in the range of 167-168 degrees, wh ile the other is in the range of 171-172.What helped me to eliminate the 4-tertbutylbenzoic acid was the equivalent weight determination. The equivalent weight s of these two acids were different, but the halogen test proved that this unkno wn contained a halogen and the halogen that 5-chloro 2-hydroxybenzoic acid conta ins is chlorine.