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Lab Report 1

by: Mallory Ivy

Lab Report 1 CH 237

Mallory Ivy
GPA 3.82

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This studysoup study guide contains your first organic lab quiz and an example of lab report (Separation of the Components of Panacetin).
Organic Chemistry Lab 1
Dr. Shaughnessey
Study Guide
organic lab 1, separation of panacetin, lab report, lab quiz
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This 6 page Study Guide was uploaded by Mallory Ivy on Tuesday February 23, 2016. The Study Guide belongs to CH 237 at University of Alabama - Tuscaloosa taught by Dr. Shaughnessey in Spring 2016. Since its upload, it has received 71 views. For similar materials see Organic Chemistry Lab 1 in Chemistry at University of Alabama - Tuscaloosa.

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Date Created: 02/23/16
Ivy 1 Mallory Ivy Shaughnessy CH 237­011 15 February 2016 Separation of the Components of “Panacetin” (Sample 2) Results 1. Theoretical Yield and Actual Yields Theoretical Yield= 3.00g Theoretical amount of sucrose= 0.3 g Theoretical amount of aspirin= 1.2 g Theoretical amount of unknown= 1.5 g Actual amount of sucrose recovered= 0.6710g Actual amount of aspirin recovered= 0.3672g Actual amount of recrystallized unknown recovered= 1.079g Starting mass of Panacetin= 2.9376g Actual mass recovered= 2.1172g  2 .     Composition of Panacetin with Their Respective Percentages of Recovery sucrose= (0.6710g /2.1172g) = 31.7% sucrose aspirin= (0.3672g /2.1172g)= 17.3% aspirin unknown= (1.079g / 2.1172g)= 51.0% unknown  3 .     Percent Recovery Compared to Starting Panacetin % sucrose = (0.6710g /2.9376g)= 22.8% sucrose % aspirin = (0.3672g /2.9367g)= 12.5% aspirin % unknown = (1.079g /2.9367g)= 36.7% unknown  4 .     Averages of melting ranges Starting melting point for unknown= 110 ℃ Fully melted point for unknown= 125.5 ℃ Ivy 2 Starting melting point for unknown + phenacetin= 111.5 ℃ Fully melted point for unknown + phenacetin= 12℃.5 Starting melting point for unknown + acetanilid℃= 82 Fully melted point for unknown + acetanilide= ℃6.5 5. The unknown component is phenacetin. Discussion Panacetin claims to be a mixture of sucrose, aspirin, and acetaminophen. It is  suspected, however, that this drug contains an unknown component related to  acetaminophen but illegal in the United States, either phenacetin or acetanilide. The  purpose of this experiment was to determine the percentages of each component in  Panacetin as well as identify the unknown component. Extracting the individual  components based on solubility and then observing the melting points of the unknown  component helped us determine the identity of the unknown. First, sucrose was separated  from Panacetin through its insolubility in dichloromethane and filtered out through  gravity filtration. Aspirin and the unknown were left in the dichloromethane solution,  which was transferred to a separatory funnel. Adding sodium bicarbonate separated the  two components into an aqueous layer and organic layer based on their solubilities.  Aspirin was more soluble in the aqueous layer which formed the top layer in the funnel  while the unknown remained in the dichloromethane (organic) layer. These two layers  were extracted into separate beakers. To collect the aspirin, the aqueous solution was  filtered under vacuum. A Rota Vap was then used to evaporate all of the organic solvents. The unknown solvent was then recrystallized and collected via vacuum filtration. Once  Ivy 3 the recrystallized unknown was dry, we used the Mel­Temp to test the melting point and  determine the identity of the unknown. The label of Panacetin states that it contains a mixture of sucrose, aspirin, and an  unknown component. According to the label, there should be 10% sucrose, 40% aspirin,  and 50% of the unknown component. The expected values of sucrose, aspirin and  unknown considered suffice were between 8%­12%, 35%­45%, and 45%­55%  respectively. By using the total amount recovered and dividing it by the total amount  started with, the experimental composition of the Panacetin was 31.7% sucrose, 17.3%  aspirin, and 51.0% unknown. The experimental results indicate that the unknown is  within the sufficient range. However, the percentages derived for the sucrose is  significantly greater than the acceptable range and the aspirin is significantly lower.  Although two of the three components fell within unacceptable ranges, the discrepancy  between the label and experimental values could be due to experimental error as the  percent recovery from the original mass of Panacetin was only 72%. This loss of mass  could have arisen from not completely isolating the organic layer from the aqueous layer  after the acid­base reaction and loss of substance as it dried within our lab drawers. For  these reasons, it is concluded that there is a possibility for the labeled percentages to be  accurate. Further testing would be required to affirm or deny.   Conclusion The unknown component of the Panacetin was phenacetin. This conclusion was  derived based on the melting points of the pure unknown and the unknown mixtures. The  unknown melted at an average of 110°C and continued melting until it reached about  Ivy 4 125.5°C. For the unknown and phenacetin mixture the melting range was 111.5°C­ 127.5°C. This led to the deduction that the unknown was phenacetin because the two  ranges were similar and the known melting point of phenacetin is 135°C. This was  further confirmed after testing the melting point of the unknown with acetanilide because  the sample began to melt at 82°C and completely melted at 96.5°C. Acetanilide has a  melting point of 114°C which confirms that the unknown and the acetanilide form a  mixture rather than a pure compound because the melting range is lower and much  broader. Therefore, based on these observations, the unknown compound is phenacetin.  Although there is significant confidence in this conclusion, the fully melted temperature  of my unknown is almost 10°C lower than the known melting point of phenacetin. The  unkown was not pure. This could have arisen from not completely extracting the aqueous and organic layer from the separatory funnel or not allowing the sodium bicarbonate to  fully react with the dichloromethane solution before extracting. Another possible error  could have occurred in heating the substances too quickly in the Mel­Temp. All in all, the results are significant and valid. The melting point range of the unknown and the  unknown with phenacetin are much closer to the melting point of phenacetin than the  melting point of the unknown mixed with acetanilide to the melting point of acetanilide.  It is not 100% certain due to the erroneous percent recovery values but the melting points  are validation that the unknown component of Sample 2 of Panacetin is phenacetin.  Exercises from the book  Experiment 2, Exercise 2: a) The percentage of sucrose would be higher because  there was not a significant amount of stirring to allow the aspirin and unknown  Ivy 5 components to dissolve in the dichloromethane. b) The percentage of unknown  (impure unknown) would be higher due to the inadequate dissolving of the aspirin in the aqueous layer. c) Adding the HCl to the dichloromethane solution would  inhibit the deprotonation of aspirin inhibiting its extraction. It would be very hard  to isolate the aspirin from the unknown/dichloromethane layer. d) It wouldn’t  protonate so it would remain in the water solution, unable to be collected.  If the  dichloromethane is neutral, then the two layers would not separate and you could  not extract the aspirin.  Experiment 2, Exercise 3: Both aspirin and the unknown (acetaminophen) would  be deprotonated with NaOH and be found in the aqueous layer. You would still be left at square one trying to isolate the two from one another. Both will form water  soluble salts.   Experiment 3, Exercise 2: X is the compound phenyl succinate. An impure  substance typically has a lower and broader melting point range than of its known  component. X + benzoic acid exhibited a melting point with a 32°C decrease. X  with m­aminophenol resulted in a 20°C decline. When X is mixed with phenyl  succinate, the melting point errs by a single degree. For this reason, we can be  confident that compound X is in fact phenyl succinate based on the known  melting point of phenyl succinate. 


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