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Aspirin Synthesis Formal Lab Report

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Dane Brown

on 16 April 2013

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Transcript of Aspirin Synthesis Formal Lab Report

Further Analysis
When was aspirin first synthesized, by whom, and for what purpose?
German chemist Felix Hoffmann synthesized what would become known as aspirin in 1899 while working for Bayer. He utilized the product to help his father who was suffering from arthritis. Though Hoffmann was the first to market the product, Charles Frederic Gerhardt had synthesized the same acid in 1853 however he made no attempt to market it ("History of Aspirin").
Describe the Kolbe synthesis for the production of salicylic acid. Show the reaction.
This is a process by which sodium phenoxide, is heated with carbon dioxide, as well as high pressure to create sodium salicylate. This compound is furthermore acidified producing salicylic acid, the precursor to aceytlsalicylic acid, aspirin.

What are the analgesics and how do they work? To which major class of analgesics does aspirin belong?
Analgesics are a group of pain relieving drugs designed to eliminate pain and inflammation by acting on the peripheral and central nervous systems. Aspirin belongs to class of analgesics called non-steroidal anti-inflammatory drugs (NSAIDs) ("Analgesic.").
Ibuprofen and acetaminophen are examples of other analgesics. Show their structures and molecular formulas. Under what brand name is each of them sold in the United States?
Ibuprofen: ("Ibuprofen")
Molecular formula: C13H18O2

Brand names: Advil, Brufen, Ibufen, and Motrin
Acetaminophen: ("Acetaminophen.") ("Paracetamol.")
Molecular formula: C8H9NO2

Brand names: Tylenol, Paracetamol, and Panadol Aspirin Lab D.A.D. Beginning with Lab 1, our lab group sought to produce an aspirin sample as well as crudely test this sample for purity. Following the previously listed procedure, we were able to accomplish both tasks. The results of our ferric chloride purity test demonstrated to us that our aspirin sample had a relatively low purity as shown by the light purple color in the test video. This could be attributed to the late addition of the catalyst during heating and the poor functionality of our thermometer. Moving into Lab 2, our lab group was tasked with producing and standardizing an approximately .100 M solution of NaOH. This was carried out through following our procedure which resulted in three separate concentrations from the three trials. The calculations for these trials produced values of .103 M, .103 M, and .102 M. Given the consistency of the calculations, significant error cannot be attributed to this particular lab. For Lab 3, our lab group was to prepare and standardize a solution of HCl. This was accomplished by preparing a 500mL bottle of approximately 0.1 M HCl through titrating it with acid, then using the base to distinguish a faint green color, indicating the ending point. These titrations were carried out three times. The molarity of the acid solution was calculated in each trial to be .0936M, .0919 M, and .0924 M. From these values, we arrived at an average concentration for our HCl solution of .0926 M. The difference in values can be attributed to varying levels of success when attempting to titrate the HCl to a faint green color. After the 3rd lab, we used our standardized NaOH and HCl solutions to quantitatively analyze our synthesized aspirin sample. By following our procedure, we found that our aspirin sample was 101 % pure (acetylsalicylic acid). This result does not match our qualitative observation of our sample in lab 1 when the ferric chloride test distinguished the impurity of our solution. This can only be explained by the concept of error carried forward. We are very confident that we properly carried out each procedure, but are not confident in the calculated molarity of our HCl solution due to the varying results of the titrations in lab 3. If the molarity of the HCl solution was different than our calculated value, it would lead to incorrect calculations of moles of acid used in the titration and hydrolysis of our aspirin sample, therefore leading to an incorrect calculation of percent purity. If we knew the correct molarity of our HCl solution, we could more accurately calculate the percent purity of our aspirin sample. Calculations Step 1: Prepare 500mL of 0.1 Molar HCl
-Dilute 17mL of 3M HCl to 500mL in reagent bottle. Lab 1: The Synthesis of Aspirin Lab 4: Lab 3: Objective:
To synthesize aspirin
Conduct a simple purity test on the aspirin sample Materials Chemical Reagents Equipment Objective: to prepare and Standardize a solution of HCl. Step 2: Titrate
-Wash each burette with respective solution twice.
- Drain 20mL of acid from acid burette into 100mL flask. Add 3 drops of bromthymol blue indicator.
-Titrate with base to faint green end point. Washed Burets Bromthymol Blue Titration
Video Mixing Solution Collecting 17mL
of 3M HCl Step 3:
-Do 3 Titrations (Steps 1 & 2 x3)
-Calculate volume of acid and base used for each trial Table: Lab 2: 1. Prepare 0.1M NaOH solution:
Weigh out 4g of NaOH into 1L bottle.
Fill bottle with Distilled water.
Shake the bottle until the solid NaOH dissolves. 2. Prepare burette:
Rinse it twice with NaOH solution.
Fill the burette, including the tip, with the solution. 3. a) Weigh out 3 samples for KHP (b/w 0.4g-0.6g). Transfer one sample at a time into a 125mL Erlenmeyer flask. Trial 1 Trial 2 Trial 3 b) Pipette 50.00mL of distilled water into flask. c) Swirl to dissolve KHP. d) Add 2 drops of phenolphthalein. 4. a) Record the starting volume on the burette. b) Titrate the KHP solution to the first appearance of a faint pink color that persists for at least 20 seconds. c) Record the final
volume on the burette. d) Rinse flask with distilled water and dry it. Trial 1 5. Do the titration 3 times: once for each measured sample of KHP. DATA 2. Place 2.0 g of salicylic acid in a 125-mL Erlenmeyer flask 1. Place approximately 200 mL of water into a 400 mL beaker and allow to warm to 70°C on a hot plate 3. Add 4.0 mL of acetic anhydride and 7 drops of 85% phosphoric acid. 4. Swirl the flask thoroughly to mix all reagents. 5. Place the flask into the 70°C water bath and heat for 10 minutes 6. Remove the flask from the water bath and add 2 mL of ice-cold distilled water while swirling. 7. Add 10 g of ice to the Erlenmeyer flask and place it in an ice bath. Allow flask to cool for approximately 10 minutes 8. Prepare Buchner funnel with filter paper. Then, set up a vacuum filtration apparatus. (Filter flask, flask adapter, rubber tubing and Buchner funnel. 9. Collect product in the Buchner funnel via vacuum filtration. 10. Wash the crystals several times during filtration with ethanol. 11. Keep the aspirator on for about 10 minutes. 12. Sample collected from the apparatus Ferric Chloride Test 1. Fill 3 test tubes with 4 mL of distilled water and place them in a test tube rack. 2. Dissolve an equal amount of product into both the first and second test tubes. The third test tube remains only filled with distilled water. 3. Add 6 drops of 1% ferric chloride solution to all 3 test tubes. (This serves as the data for our lab1) The Synthesis of Aspirin Trial 2 Step 1: Weigh 0.521 g of our synthesized aspirin. Step 2: Prepare an acid buret with our HCL solution and a basic buret with our NaOH solution, recording initial readings. step 3: combine aspirin sample with 25 mL of cooled ethyl alcohol in a flask and swirl to dissolve. Step 4: Add 2 drops of phenolphthalein then titrate the sample in the flask to a faint pink using the NaOH. Step 5: Add approx 43.51 mL of NaOH for Hydrolysis. Step 6: Heat Mixture for 15 minutes in a boiling water bath, then remove the flask and cool to room temperature in an ice water bath. Step 7: Back-titrate using the HCl solution until the pink color disappears (or is barely there). Record initial and final volumes. Table of Collected (And some Calculated) Data Objective: To determine the purity of the synthesized aspirin. Quantitative Analysis of Aspirin Conclusion Chemical Reagents: 0.0926 M HCl (Hydrochloric Acid)
0.103 M NaOH (Sodium Hydroxide)
Synthesized Aspirin Sample (exact formula unknown)
95% Ethanol (C2H60) Advance slide show to see reaction Advance again to return to Further Analysis Advance slide show to view molecule Advance again to return to Further Analysis
What are some of the supposed benefits of taking aspirin aside from pain relief?
Aspirin is said to additionally reduce risk of heart attack, stroke, cancer of the colon, esophagus, stomach, rectum, and prostate as well as protection against Alzheimer's disease ("Men's Health").
What is Reye's syndrome? What is its connection to aspirin?
Reye's Syndrome is an illness occurring following a viral infection and results in damage to the organs, especially the liver and brain. It can strike quickly and lead to death. Reye's Syndrome is seen to typically develop after a person consumes aspirin while dealing with a viral infection such as influenza, cold or the chicken pox ("What is Reye's Syndrome?"). Advance slide show to view molecule Advance again to return to Further Analysis Works Cited

"Acetaminophen." Acetaminophen. N.p., n.d. Web. 11 Apr. 2013.

"Analgesic." Wikipedia. Wikimedia Foundation, 04 Nov. 2013. Web. 11 Apr. 2013.

"Aspirin." - Molecule of the Month. N.p., n.d. Web. 11 Apr. 2013.

"History of Aspirin." History of Aspirin. N.p., n.d. Web. 11 Apr. 2013.

"Ibuprofen." Water Treatability Database. N.p., n.d. Web. 11 Apr. 2013.

"Men's Health." An Aspirin a Day ... or Not? N.p., n.d. Web. 11 Apr. 2013.

"Paracetamol." Wikipedia. Wikimedia Foundation, 04 Nov. 2013. Web. 11 Apr. 2013.

"What Is Reye's Syndrome - National Reye's Syndrome Foundation." What Is Reye's Syndrome - National Reye's Syndrome Foundation. N.p., n.d. Web. 11 Apr. 2013. Objective: to prepare and standardize approx. .100 M NaOH solution Equipment: Chemical Reagants: Calculations Equipment: Chemical Reagants: Step 4:
-Calculate the molarity of the acid solution in each trial
-Determine the average concentration of HCl Calculations Equipment: Milligram Balance
Erlenmeyer Flask
2 Burettes with acid-base titration set up
Phenolphthalein indicator
Beaker with ice
Hot plate with boiling water bath Preparation and Standardization of HCl Preparation and Standardization of Sodium Hydroxide Solution Questions Trial 1 Trial 2 Trial 3 Equations 1. We used the volume of NaOH in the titration to determine the number of moles of NaOH added for hydrolysis, through stoichiometry.

2. We used the volume of HCL used in the back titration to determine the number of moles of HCl used through stoichiometry. 3. We equated the moles of HCl used in the back titration with the moles of NaOH still present in the solution.

4. We then calculated the moles of NaOH used in hydrolysis by subtracting the moles of NaOH still present in the solution from the total number of moles added for hydrolysis. 5. We equated the moles of NaOH used in the hydrolysis to the number of moles of acetylsalicylic acid present.

6. We found the mass of acetylsalicylic acid present by multiplying the number of moles by the molar mass of the substance. 7. We demonstrated our total sample mass from the data obtained in the procedure.

8. By comparing our calculated mass of acetylsalicylic acid to the actual weight of our sample and multiplying by 100, we determined the purity of our aspirin sample. Equation: Dane Brown
Alexa Megaludis
Dan Mrachko
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