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Separating acids post lab, Papers of Organic Chemistry

University of Houston (UH)Organic Chemistry

separating lab acids post lab orgo 1

Typology: Papers

2022/2023

Uploaded on 02/21/2024

avery-perez
avery-perez 🇺🇸

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Separating Acids and Neutral Compounds by Solvent
Extraction
Post-Lab 10/02/23
VII. Calculations:
1. Calculate the percent recovery of each of the compounds recovered from
the original mixture.
a) P-toluic acid: my filter paper weighed 0.462g. The weight of my recrystallized
p-toluic acid with the filter paper was 0.625g. So, 0.625g-0.462g
= 0.163g
%recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%)
=(0.163g/1.307g) x 100
= 12.5%
b) P-tert-butylphenol: my filter paper weighed 0.470g. the weight of my
recrystallized p-tert-butylphenol with the filter paper was 1.006g.
So, 1.006g-0.470g
= 0.536g
%recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%)
=(0.536g/1.307g) x 100
= 41.0%
c) Acetanilide: my round bottom flask weighed 62.216g. The weight of my
recrystallized acetanilide with the RBF was 62.971g. So, 62.971g- 62.416g
=0.555g
%recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%)
=(0.555g/1.307g) x 100
= 42.5%
VIII. Results and Discussions:
The results of the experiment showed that the melting point of each compound are closely
similar to the actual ranges of the melting points for each compound. This shows that comparing
them to the literature values the compounds are pure. The results I got for my %recovery is very
high and show great results! For the TLC plates my Rf values show that the toluic acid was the
faster moving compound meaning its less polar than the other compounds. The tert-butyl was the
middleman and was right behind the toluic acid and lastly the acetanilide was the most polar and
moved the slowest. I think that since my toluic TLC plate couldn’t fully develop I got wrong
results because the tert-butyl should’ve been the least polar out of all the compounds.
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Separating Acids and Neutral Compounds by Solvent

Extraction

Post-Lab 10/02/

VII. Calculations:

1. Calculate the percent recovery of each of the compounds recovered from the original mixture. a) P-toluic acid: my filter paper weighed 0.462g. The weight of my recrystallized p-toluic acid with the filter paper was 0.625g. So, 0.625g-0.462g = 0.163g %recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%) =(0.163g/1.3 0 7g) x 100 = 12. 5 % b) P-tert-butylphenol: my filter paper weighed 0.470g. the weight of my recrystallized p-tert-butylphenol with the filter paper was 1.006g. So, 1.006g-0.470g = 0.536g %recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%) =(0.536g/1.3 0 7g) x 100 = 41.0% c) Acetanilide: my round bottom flask weighed 62.216g. The weight of my recrystallized acetanilide with the RBF was 62.971g. So, 62.971g- 62. 416 g =0.555g %recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%) =(0. 555 g/1.3 0 7g) x 100 = 42.5%

VIII. Results and Discussions:

The results of the experiment showed that the melting point of each compound are closely similar to the actual ranges of the melting points for each compound. This shows that comparing them to the literature values the compounds are pure. The results I got for my %recovery is very high and show great results! For the TLC plates my Rf values show that the toluic acid was the faster moving compound meaning its less polar than the other compounds. The tert-butyl was the middleman and was right behind the toluic acid and lastly the acetanilide was the most polar and moved the slowest. I think that since my toluic TLC plate couldn’t fully develop I got wrong results because the tert-butyl should’ve been the least polar out of all the compounds.

IX. Conclusion: I learned that if the experiment is done somewhat correctly, you’ll get the correct outcome of the experiment. Each melting point lined up with the actual melting points that were given. Also, I learned that I feel like if we had more time for the week after to take time and do the TLC and the melting point, we wouldn’t be so rushed. I felt rushed and everywhere all at once since we needed to do another experiment that was a lot more work. Overall, a very fun experiment! X. Post-Lab Questions:

2. Calculate the percent recovery of each of the compounds recovered from the original mixture. d) P-toluic acid: my filter paper weighed 0.462g. The weight of my recrystallized p-toluic acid with the filter paper was 0.625g. So, 0.625g-0.462g = 0.163g %recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%) =(0.163g/1.3 0 7g) x 100 = 12. 5 % e) P-tert-butylphenol: my filter paper weighed 0.470g. the weight of my recrystallized p-tert-butylphenol with the filter paper was 1.006g. So, 1.006g-0.470g = 0.536g %recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%) =(0.536g/1.3 0 7g) x 100 = 41.0% f) Acetanilide: my round bottom flask weighed 62.216g. The weight of my recrystallized acetanilide with the RBF was 62.971g. So, 62.971g- 62. 416 g =0.555g %recovery= (mass of recrystallized compound, g/ mass of crude compound, g) (100%) =(0. 555 g/1.3 0 7g) x 100 **= 42.5%

  1. If you mistakenly extracted the ether solution first with NaOH solution and then with NaHCO 3 solution, no crystals would be produced upon acidification of the NaHCO 3 layer. Briefly explain.** NaHCO 3 can neutralize both acids and bases, and compared to a NaOH is a strong base. If NaOH is used in the beginning on the ether solution, the NaOH can overpower the compound. This can lead to the is leaving now compound for the NaHCO 3 to interact accurately. 4. What product would you obtain if you evaporated the water from the NaOH layer prior to acidifying the layer?