Aspirin Synthesis
.docx
keyboard_arrow_up
School
University of South Florida *
*We aren’t endorsed by this school
Course
2211
Subject
Chemistry
Date
Apr 3, 2024
Type
docx
Pages
4
Uploaded by shannonscott
Aspirin Synthesis
Shannon Scott
Section 602
Shanelle Suepaul
10/31/2022
Introduction:
The purpose of this experiment is to synthesize aspirin from salicylic acid and acetate anhydride. We will also be determining whether the reaction has completed by using TLC. in order to synthesize aspirin we have to perform an esterification. An ester group is a very important functional group that can be synthesized in different ways. One type of synthesizing technique for an ester is called a fischer esterification. in this esterification A carboxylic acid and a alcohol react together when they’re in the presence of a catalyst. In order for this to be done The carboxylic acid and the alcohol has to be heated while being in the presence of a catalyst. in this experiment aspirin how is an ester functional group. Aspirin is a very versatile drug that is used in the world of medicine. It is also one of the oldest drugs to be used in medicine. Some abilities are aspirin has is painkilling, reducing fever, prevents blood clots and ask for anti-inflammatory. Aspirin has also been used and has been found very effective in treating arthritis.
Materials:
1 g of salicylic acid
2 mL of acetate anhydride
5 drops of concentrated sulfuric acid
50 mL Erlenmeyer flask
magnetic star bar
TLC plate 9ml hexane and 1ml ethyl acetate
water
vacuum filter heat source beaker
Procedures:
We are going to take 1 g of salicylic acid and mix 2.5 mL of acetate anhydride in it. then add in five drops of concentrated sulfuric acid. put all of that into a Erlenmeyer flask with a spin bar. then take the TLC of the mixture. While the TLC mixture is going heat the reaction mixture on a hot plate for 10 minutes. After 10 minutes take the TLC of the mixture again. Allow the mixture to room temperature and then put it into an ice bath for it to crystallize. Now add 20 mL of cold water to the flask and stare carefully. Do a vacuum filtration using the Büchner funnel to filter the crystals. Then rinse the crystals with ice cold water. Allow the solution to cool the room temp
and then place another ice bath to complete recrystallization. Now weigh the dry crystal and determine the melting point.
Data:
Product
Weight (g)
Aspirin
0.2282
Spot #
Distance traveled
Spot 1
6.5 cm
Spot 2
5.5 cm
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
- Access to all documents
- Unlimited textbook solutions
- 24/7 expert homework help
Related Questions
In a 0.73 mM aqueous solution of trimethylacetic acid (C₂H₂CO₂H), what is the percentage of trimethylacetic acid that is
dissociated? You can find some data that is useful for solving this problem in the ALEKS Data resource.
Round your answer to 2 significant digits.
1%
00
x10
X
$
arrow_forward
1. For alcohol protecting groups, there are many
options, including converting the alcohol to an
ester (we will see this in Chapter 20). In the
context of organometallic chemistry, why would
an ester be a poor choice? Use the following
reaction as an example and point out what could/
would happen.
Mg
OH
then
2. I did not quite get to it, but organometallic
reagents can react with other functional groups
beyond carbonyls. One significant example is
epoxides. Given that they are strong
nucleophiles, what do you think would be the
product of the following reaction.
i
3. And then synthesis. Outline how you could
covert the given ester to the given tertiary
alcohol. Note that you may have to look at
chapter 17 for a review of some older reactions if
you do not remember them.
from
arrow_forward
Please fill in the charts for the ester lab (chemistry)
arrow_forward
On synthesis of esters via nucleophilic acyl substitution:
How is excess alcohol eliminated from the crude product?
Write the chemical equation involved in the reaction between the excess acid and NaHCO3. Given this, briefly explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid.
arrow_forward
In this lab you are performing your first organic synthesis and safety information on all the materials you are using must be obtained.
Companies are required to provide material safety data sheets (MSDS) for chemical compounds they sell.
Please examine the MSDS for acetic anhydride, available here. You will find GHS pictograms within the sheet that summarize the
main hazards of this compound. The pictograms are essentially the same as the symbols on WHMIS labels, available here for
reference.
Based on the pictograms, whatare the main hazards for acetic anhydride? Select as many answers as appropriate
Select one or more:
Carcinogen
Gas under pressure
Acute oral or inhalation toxicity
Corrosive
Flammable material
Oxidizing material
Self-reactive substance
arrow_forward
On synthesis of esters via nucleophilic acyl substitution:
Write the chemical equation involved in the reaction between the excess acid and NaHCO3. Given this, briefly explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid. Also, explain how excess alcohol was eliminated from the crude product.
arrow_forward
Find the structural formulas for salicylic acid, acetic anhydride, and aspirin. Use these structural formulas to construct a reaction equation describing the synthesis of aspirin.
(CH3CO)2O
+
HOC6H4COOH
→
CH3CO2C6H4CO2H
+
CH3COOH
acetic anhydride
salicylic acid
acetylsalicylic acid
acetic acid
Part I Synthesis of Aspirin
Mass of salicylic acid used (g)
2.029g
Volume of acetic anhydride used (mL)
5ml
Mass of acetic anhydride used (vol. × 1.08 g/mL)
5.4g
Mass of aspirin synthesized (g)
3.256g
Part II Melting Temperature Data
Melting temperature (°C)
133°C
Part III Salicylic Acid Standard Stock Solution
Initial mass of salicylic acid (g)
0.210g
Moles of salicylic acid (mol)
0.0147 mol
Initial molarity of salicylic acid (M)
0.724 M
Part III Beer’s Law Data for Salicylic Acid Standard Solutions
Trial
Concentration (M)
Absorbance
Water (mL)
1
10
0.301
0…
arrow_forward
Please help me with these chemistry worksheets
arrow_forward
Figure 3 shows a substitution reaction between triphenylmethyl chloride and an excess of the base methanamine. What is the minimum mass of this amine required to produce 5.000 grams of the organic product N-methyltriphenylmethanamine? Molar masses are given in Figure 3. [Round the answer to three decimal places. Do not type in the unit. Use a decimal point.] *
Do you need to add imidazole to the reaction mixture used in this question to absorb the hydrogen chloride gas produced during the reaction?
arrow_forward
Write TRUE if the underlined word/phrase makes the statement correct. Otherwise, write the correct WORD/PHRASE that will make the statement true.
a. 2-phenylacetaldehyde is soluble with concentrated sulfuric acid due to acid-base neutralization.
b. 2-phenylacetic acid has a solubility classification of A2, which means it is soluble in 5.O%NaOH and insoluble in 5.O% NaHCO3.
c. Scratching the inner sides of the beaker to begin recrystallization is advised for unsaturated solutions.
d. Washing with hot solvent eliminates adhered mother liquor and avoids crystal dissolution.
e. To extract a nonpolar organic compound using solvent extraction, the extracting solvent must be nonpolar, and the washing solvent must be also nonpolar.
f. Addition of 6.0 M NaCl extracts saponins by converting them to their salt form.
g. The stationary phase in the paper chromatography experiment is the filter paper.
h. When the spots have low concentration, they will not be observed as visible spots in the…
arrow_forward
4. You are given a mixture of sodium benzoate and cyclohexylammonium chloride (structures
below) that are dissolved in water at pH 7.0. You enter the lab and quickly find a separatory
funnel, an organic solvent, sodium hydroxide, concentrated hydrochloric acid, and water. Devise
a way to separate these two molecules using a simple organic extraction method. Clearly
indicate which molecule is in the organic layer and which molecule is in the aqueous layer.
Justify your method by describing what is happening at the molecular level.
NH3*
Cl-
Na+
pka = 4.2
pka = 11.2
%3D
arrow_forward
Why does the dehydration of an alcohol more often use concentrated sulfuric acid,
H2SO4H2SO4, as the acid catalyst rather than dilute hydrochloric acid,
HCl?
Select one or more:
Hydrochloric acid is too small to effectively react with the alcohol in the reaction.
The additional water solvent from a dilute solution could reverse the dehydration reaction.
Only acids with more than one proton can complete the dehydration reaction.
The presence of the chloride ion could result in a competing substitution reaction.
arrow_forward
Which solvent(s) would be suitable for substitution reactions using NaCN?
Acetonitrile
Benzene
Diethyl ether
Methanol (MeOH)
Dimethylformamide (DMF)
Acetone.
Isopropanol
arrow_forward
In a small laboratory, the following organic synthesis was under performance. However, the sample had caught fire and ignited. What type of extinguishing method should be taken? If a fire extinguisher is used what type of it should be used? Explain the reasoning behind your choices
arrow_forward
Organic Functional Groups
Predicting the reactants or products of ester hydrolysis
Predict the products of this organic reaction:
0
CH—C—0—CH,
H
C-CH3
+ H₂O
Specifically, in the drawing area below draw the condensed structure of the product, or prod
in any arrangement you like, so long as they aren't touching.)
If there aren't any products because this reaction won't happen, check the No reaction box un
arrow_forward
Consider a ternary (three-component) system of amphiphile, hydrocarbon, and water. What structure do you expect to form if small amounts of the first two components are mixed with a large amount of water?
arrow_forward
Predict the most likely product of this biochemical reaction:
CH₂=
OH O
+ Pi
X + H₂O
That is, in the drawing area below, draw the chemical structure of the product molecule X.
Note for advanced students: you can assume any necessary small-molecule reactants, like water, are available.
Predicting reactants or products of
phosphorylation
Click and drag to start drawing a
structure.
X
Ś
(
arrow_forward
You are employed as a coop student at the Drug and Alcohol Testing Association of Canada (DATAC) developing analytical tests for sports doping agents. You are asked to prepare a procedure for the extraction of methylphenidate, the active compound in Ritalin, from urine samples (consider them as simple aqueous layers, you do not need to consider other components!). The goal of the procedure is to extract the methylphenidate into an organic layer which will then be evaporated, and the residue will be tested for the drug.You find that methylphenidate is highly soluble in 2-methyltetrahydrofuran, a bio-renewable solvent. Draw the structure of 2-methyltetrahydrofuran and give two reasons why it is a good solvent choice for liquid-liquid extraction.
arrow_forward
Restate the paragraph.
The main objective of the laboratory activity was to make aspirin also known as acetylsalicylic acid in its scientific name. It was successfully done as aspirin was synthesized using the combination of salicylic acid and acetic anhydride. In this reaction, salicylic acid's hydroxyl group on the benzene ring interacted with acetic anhydride to generate an ester functional group. This is an esterification reaction that produces acetylsalicylic acid. Sulfuric acid was utilized as a catalyst to start the esterification reaction. Some unreacted acetic anhydride and salicylic acid, as well as sulfuric acid, aspirin, and acetic acid, remained in the solution after the reaction was completed. The process of crystallization was used to obtain pure crystals of a substance from an impure mixture. Upon completion of the lab, analysis, and calculations, , it is evident that the synthesis of aspirin is possible using these methods but that the yield will be relatively low
arrow_forward
4. Using structures for all species, write the complete esterification reaction begun below:
HSO,
methanol (CH3OH) + salicylic acid
arrow_forward
You want to determine the molar mass of the polymer shown below by end
group analysis using acid-base titration. 15 grams of this polymer dissolved in
water consumed 6 mL of 0.1 M NaOH. What is the number average degree of
polymerization (disregarding end groups)?
но
OH
1136
462
398
236
568
arrow_forward
SYNTHESIS OF ESTERS VIA NUCLEOPHILIC ACYL SUBSTITUTION
Write the chemical equation involved in the reaction between the excess acid and NaHCO3.
Explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid.
How was excess alcohol eliminated from the crude product.
arrow_forward
only the questions pls disregard the experiment results thank you
arrow_forward
What functional group is present in the reactants (isobutanol, sulfuric acid, Dichloromethane, sodium carbonate) but not in the ester? What wave number range in the IR spectrum does the peak appear and what does it look like?
arrow_forward
Estrogens are female sex hormones, the most potent of which is B-estradiol.
OH
AYA
Но
B-Estradiol
In recent years, chemists have focused on designing and synthesizing molecules that
bind to estrogen receptors. One target of this research has been nonsteroidal estrogen
antagonists, compounds that interact with estrogen receptors and block the effects of
both endogenous and exogenous estrogens. A feature common to one type of nonste-
roidal estrogen antagonist is the presence of a 1,2-diphenylethylene with one of the
benzene rings bearing a dialkylaminoethoxyl substituent. The first nonsteroidal estrogen
antagonist of this type to achieve clinical importance was tamoxifen, now an important
drug in the treatment of breast cancer. Tamoxifen has the Z configuration shown here.
NMeg
A
B
NMeg ?
ОН
Tamoxifen
Propose reagents for the conversion of A to tamoxifen. Note: The final step in this
synthesis gives a mixture of E and Z isomers.
arrow_forward
Hi! I am working on some Organic Chemistry homework and one of the questions asked what would happen if Butanol was used as a solvent instead of water when mixed with methanol,ethanol, and hexan-1-ol
arrow_forward
Why are alcoholic solutions (alcoholic NH2OHꞏHCl, alcoholic KOH, alcoholic HCl) used in the hydroxamic acid test for esters? Please don't answer if you've answered this already.
arrow_forward
Provide both a model and structural formula for each question.
arrow_forward
4. A student prepared a compound. The melting point of the crude product was 42 to 48°C.
After purifying the solid for the first time, the melting point was 47 to 51°C. After another
purification, the melting point was 50 to 53°C. At this stage, can the student confidently
say the product has been completely purified? Justify your answer.
ied
arrow_forward
SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Related Questions
- In a 0.73 mM aqueous solution of trimethylacetic acid (C₂H₂CO₂H), what is the percentage of trimethylacetic acid that is dissociated? You can find some data that is useful for solving this problem in the ALEKS Data resource. Round your answer to 2 significant digits. 1% 00 x10 X $arrow_forward1. For alcohol protecting groups, there are many options, including converting the alcohol to an ester (we will see this in Chapter 20). In the context of organometallic chemistry, why would an ester be a poor choice? Use the following reaction as an example and point out what could/ would happen. Mg OH then 2. I did not quite get to it, but organometallic reagents can react with other functional groups beyond carbonyls. One significant example is epoxides. Given that they are strong nucleophiles, what do you think would be the product of the following reaction. i 3. And then synthesis. Outline how you could covert the given ester to the given tertiary alcohol. Note that you may have to look at chapter 17 for a review of some older reactions if you do not remember them. fromarrow_forwardPlease fill in the charts for the ester lab (chemistry)arrow_forward
- On synthesis of esters via nucleophilic acyl substitution: How is excess alcohol eliminated from the crude product? Write the chemical equation involved in the reaction between the excess acid and NaHCO3. Given this, briefly explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid.arrow_forwardIn this lab you are performing your first organic synthesis and safety information on all the materials you are using must be obtained. Companies are required to provide material safety data sheets (MSDS) for chemical compounds they sell. Please examine the MSDS for acetic anhydride, available here. You will find GHS pictograms within the sheet that summarize the main hazards of this compound. The pictograms are essentially the same as the symbols on WHMIS labels, available here for reference. Based on the pictograms, whatare the main hazards for acetic anhydride? Select as many answers as appropriate Select one or more: Carcinogen Gas under pressure Acute oral or inhalation toxicity Corrosive Flammable material Oxidizing material Self-reactive substancearrow_forwardOn synthesis of esters via nucleophilic acyl substitution: Write the chemical equation involved in the reaction between the excess acid and NaHCO3. Given this, briefly explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid. Also, explain how excess alcohol was eliminated from the crude product.arrow_forward
- Find the structural formulas for salicylic acid, acetic anhydride, and aspirin. Use these structural formulas to construct a reaction equation describing the synthesis of aspirin. (CH3CO)2O + HOC6H4COOH → CH3CO2C6H4CO2H + CH3COOH acetic anhydride salicylic acid acetylsalicylic acid acetic acid Part I Synthesis of Aspirin Mass of salicylic acid used (g) 2.029g Volume of acetic anhydride used (mL) 5ml Mass of acetic anhydride used (vol. × 1.08 g/mL) 5.4g Mass of aspirin synthesized (g) 3.256g Part II Melting Temperature Data Melting temperature (°C) 133°C Part III Salicylic Acid Standard Stock Solution Initial mass of salicylic acid (g) 0.210g Moles of salicylic acid (mol) 0.0147 mol Initial molarity of salicylic acid (M) 0.724 M Part III Beer’s Law Data for Salicylic Acid Standard Solutions Trial Concentration (M) Absorbance Water (mL) 1 10 0.301 0…arrow_forwardPlease help me with these chemistry worksheetsarrow_forwardFigure 3 shows a substitution reaction between triphenylmethyl chloride and an excess of the base methanamine. What is the minimum mass of this amine required to produce 5.000 grams of the organic product N-methyltriphenylmethanamine? Molar masses are given in Figure 3. [Round the answer to three decimal places. Do not type in the unit. Use a decimal point.] * Do you need to add imidazole to the reaction mixture used in this question to absorb the hydrogen chloride gas produced during the reaction?arrow_forward
- Write TRUE if the underlined word/phrase makes the statement correct. Otherwise, write the correct WORD/PHRASE that will make the statement true. a. 2-phenylacetaldehyde is soluble with concentrated sulfuric acid due to acid-base neutralization. b. 2-phenylacetic acid has a solubility classification of A2, which means it is soluble in 5.O%NaOH and insoluble in 5.O% NaHCO3. c. Scratching the inner sides of the beaker to begin recrystallization is advised for unsaturated solutions. d. Washing with hot solvent eliminates adhered mother liquor and avoids crystal dissolution. e. To extract a nonpolar organic compound using solvent extraction, the extracting solvent must be nonpolar, and the washing solvent must be also nonpolar. f. Addition of 6.0 M NaCl extracts saponins by converting them to their salt form. g. The stationary phase in the paper chromatography experiment is the filter paper. h. When the spots have low concentration, they will not be observed as visible spots in the…arrow_forward4. You are given a mixture of sodium benzoate and cyclohexylammonium chloride (structures below) that are dissolved in water at pH 7.0. You enter the lab and quickly find a separatory funnel, an organic solvent, sodium hydroxide, concentrated hydrochloric acid, and water. Devise a way to separate these two molecules using a simple organic extraction method. Clearly indicate which molecule is in the organic layer and which molecule is in the aqueous layer. Justify your method by describing what is happening at the molecular level. NH3* Cl- Na+ pka = 4.2 pka = 11.2 %3Darrow_forwardWhy does the dehydration of an alcohol more often use concentrated sulfuric acid, H2SO4H2SO4, as the acid catalyst rather than dilute hydrochloric acid, HCl? Select one or more: Hydrochloric acid is too small to effectively react with the alcohol in the reaction. The additional water solvent from a dilute solution could reverse the dehydration reaction. Only acids with more than one proton can complete the dehydration reaction. The presence of the chloride ion could result in a competing substitution reaction.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning