Ashogbon, Habib

Title Purification and identification of an unknown organic acid (111011-AS12)

As a chemistry student learning about everything that makes us what we are from our existence to our tiny bit of atom, understanding how to purify and identify an unknown organic compound is a favorable place to begin the acquisition of necessary knowledge to achieving success. There are so many unknown organic acids in existence today, but the similar properties my acid share with other acids would help me narrow my choices down to identifying my unknown acid (111001-AS12). My goal is to study what happens when I re-crystallize my acid, check the melting point, and find the equivalent weight. My findings would be used to narrow down a potential compound name for my acid which would be found through a computer search (see appendix) based on my data.

Purification and recrystallization of the acid The purification of an acid is the first basic step to determining its true properties because an impurity would alter my unknown acids chemical properties. My recrystallization required me to dissolve 10.0010g of my unknown in a water and ethanol solution. I ended up using only 200mL of water as my solvent. After recrystallizing my acid, I ended up with 4.7180g of recrystallized substance, and my percent recovery (see appendix) is estimated to be 47.18%. The loss in yield is made up by the high gain in purity. The purity of the material can be determined due to the sharpness and veracity of the melting point data derived.

Melting Point Melting point plays a big role in identifying any unknown organic acid. If the recrystallized acid is left with impurities there would be error associated with the data acquired which would mean a lower melting point and large range. I did 4 different melting point range

crude solid, standard, recrystallized substance, and 2nd recrystallized substance (recrystallizing the recrystallized substance), and my data were 138-148, 151-153,130-133, and 130-133 respectively. The reason for the 2nd recrystallization is to verify the purity of the substance. My melting point shows some impurities have been be removed because the melting point of my crude solid is different from the melting point of my recrystallized. The melting point of my recrystallized subsatnce matches a possible melting point of one of my compound name found in my computer search (see appendix).

Equivalent weight In finding the equivalent weight of my unknown organic acid, I used the titration method with a standard sodium hydroxide solution (NaOH), and phenolphthalein as an indicator. I prepared the NaOH solution with 800ml of H2O and 4.00ml of concentrated NaOH, and then I began titrating. First, I had to calculate the molarity (see appendix) of NaOH with the data collected when titrating with potassium hydrogen phthalate (KHP). I got my average molarity of NaOH to be 0.094166 with a percent deviation of 0.2029%. Secondly, I looked for the molarity of HCl solution by titrating it with my NaOH solution. I calculated the average molarity of the HCl solution to be 0.2098 with percent deviation of 0.1483% based off the data retrieved from my experiment. I added 2-3 drops of phenolphthalein to play the role of an indicator. Finding the equivalent weight required the molarity of NaOH which I already calculated, volume of NaOH, and .3---g of my recrystallized substance. My average equivalent calculated was 179.5g with percent deviation of .67%. I compared this calculated equivalent weight with

the equivalent weight (see appendix) I derived from the pH vs. VNaOH graph I plotted to find the pKa, it was pretty close at 178.2g. I somewhat believe my equivalent weight should be close to 178-+5. The next step in finding my unknown acid is to search the computer for possible compound name for my acid based on my melting point and equivalent weight only because I havent derived my pKa yet. Computer Search My data produced 4 different compound names that were pretty close in respect to my data. Two of those acids had chlorine and one had nitrogen while the last didnt have any element that would require me conducting sodium fusion. The pKa were within 3.5-+0.5 expect the compound that has nitrogen. Sodium fusion was the only way to determine if my compound has nitrogen or halogens (chlorine), and I also I had to find the pKa in order to verify the pKas given by the computer search. Sodium Fusion I conducted this experiment to check if nitrogen or halogens are present in my substance. The sodium fusion test for nitrogen didnt turn blue which indicates the absence of nitrogen. It made sense because the pKa for the compound with nitrogen was 2.55 compared to my derived pKa of 3.5. My halogen test couldnt be determined because I failed to make my solution acidic by adding diluted nitric acid HNO3. My acid would be based on the assumption if halogens were present. I had to find the pKa. to narrow my search in finding if the compounds had what it took to be my unknown acid.

Titration curve and pKa The pKa was determined by titrating .3grams of my substance with NaOH. I gathered data as the pH increases till it jumped from 6.87 10.90 (see appendix). I plotted it on a graph (see appendix) and mapped out my pKa from there which turned out to be 3.5; the exact pKa the computer search gave for 2-acetoxybenzoic acid and 3-chloro-3-pehenyl-2-propenoic acid. I also used the data collected from the graph to verify my equivalent weight of 179.5, and I got 178.2 which seem pretty close.

Conclusion I couldnt determine the presence of halogen due to slight failure in my experiment, but I strongly believe my substance contained halogens because 3-chloro-3-pehenyl-2-propenoic acids melting point is in the same range as the melting I got for my substance, while 2 acetoxybenzoic acids melting point is significantly large (see appendix). If my substance wasnt pure then my melting point should have a large range, but 2-acetoxybenzoic acid didnt. Both pKa were 3.55 and 3.57 respectively (see appendix). The equivalent weight for 2-acetoxybenzoic acid is 180 which makes it close to my calculated with 179.5 or 178.2 as calculated with the data from the pH vs. VNaOH graph. My equivalent weight for 3-chloro-3-pehenyl-2-propenoic acid is 183 compared to my calculated of 179.5 or 178.2 as calculated with the data from the pH vs. VNaOH graph. This equivalent weight is a little off with a difference of 3-4g. Id say the difference could be error in my calculations. Im positive my unknown organic acid is 3-chloro-3-pehenyl2-propenoic acid with the set of data I have. 2-cholo-3-phenyl-2-propenoic acid was excluded because its melting point significantly large too.

Appendix Melting point Crude Solid Standard Recrystallized substance 2nd Recrystallized substance 138-148 151-153 130-133 130-133

Titration of KHP (204.24g/mol KHP) Mass NaOH (L) Molarity of KHP Deviation average 0.3562 0.3509 0.3565 0.01850 0.01830 0.01850 0.09427 0.09388 0.09435 0.094166 (avg) +,- 0.0001034 +,- 0.0002866 +,- 0.0001834 +,(avg) 0.0001911 from

% deviation= (avg deviation from average/average molarity) * 100 = (0.0001911/0.094166) * 100 = 0.2029%

Titration of HCl MHCl VHCl = MNaOH VNaOH M (NaOH) Volume (NaOH) Volume (HCl) M (HCl) Deviation from avg 0.094166 0.094166 0.094166 22.30 ml 22.30ml 22.23ml 10.00ml 10.00ml 10.00ml 0.2100 0.2100 0.2093 +,- 0.0002333 +,- 0.0002333 +,- 0.0004667

Average M (HCl) = 0.2098 Average deviation from average = +, - 0.0003111 % deviation= (avg deviation from average/average molarity) * 100 = (0.0003111/0.2098) * 100 = 0.1483%

Equivalent Weight Mass/ (MNaOH * VNaOH) Mass 0.3677g 0.3653g M (NaOH) 0.094166 0.094166 V(NaOH) 0.02153 0.02182 Eq. Wt. 181.4 177.8

0.3633g

0.094166

0.02150

179.4

Average Eq. Wt. = 179.5 Deviation from Average = 1.9, 1.7, and 0.10 with an average of 1.2 % deviation = 0.67% Computer Search Results of your search for organic acids with: Melting Point: Equivalent Weight: 133 8 oC 179 12 g/eq Melting Point (oC) Equivalent Weight (g/eq) Amide Melting Point (oC) 144 - 145 Diamide Melting Point (oC) -

Chemical Name Trivial Name Formula 2-acetoxybenzoic acid acetylsalicylic acid CH3COOC6H4COOH (E)-3-chloro-3-phenyl-2propenoic acid -chloro-cis-cinnamic acid C6H5CCl=CHCOOH 5-methyl-2-nitrobenzoic acid 6-nitro-m-toluic acid CH3C6H3(NO2)COOH (Z)-2-chloro-3-phenyl-2propenoic acid -chloro-trans-cinnamic acid C6H5CH=CClCOOH

pka1 pka2

138 - 140

180

3.55

132 - 133

183

76 - 76

3.57

132 - 134

181

176 - 177

2.55

138 - 139

183

121 - 122

Titration curve and pKa

Recorded mL NaOH pH 0 2.48 1.00 2.60 2.00 2.66 3.00 2.78 4.00 2.89 5.00 2.99 6.00 3.08 7.00 3.17 8.00 3.25 9.00 3.34 10.00 3.44 11.00 3.53 12.00 3.63 13.00 3.73 14.00 3.83 15.00 3.97 16.00 4.11 17.00 4.29 18.00 4.56 19.00 5.03 20.00 6.87 21.00 10.90 21.50 11.39 22.00 11.60 22.50 11.74 23.00 11.83 23.50 11.90 24.00 11.97 24.50 12.01 25.00 12.06