Experiment 1. Synthesis of Aspirin

Organic synthesis or synthetic organic chemistry

art and science of constructing organic molecules, whose primary element is carbon, such as those found in living creatures and some synthetic materials

carbon framework or skeleton

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

1 = ?

introducing, removing or transforming

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

2 = ?

short and efficient

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

3 = ?

selective stereo-control

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

4 = ?

better

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

4.a. = ?

multiplied

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

4.b. = ?

synthesis

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

5 = ?

unwanted reaction

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

6 = ?

economic considerations

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

7 = ?

synthesis

PRINCIPLES of ORGANIC SYNTHESIS:

1. Constructing the __________________________ of the desired molecule.   

2. __________________ functional groups in a fashion that achieves the functionality of the desired compound.

3. Exercising _______________ at all stages in which centers of stereoisomerism are created or influenced.

4. Since a successful synthesis must produce the desired product in reasonable amount, it should be as __________________ as possible.

a. A two or three-step sequence is usually ____ than a six or seven step procedure, even if the individual step yields are better in the longer route.

b. Most reactions do not proceed in 100% yield, and the losses are ________ with each additional step. Furthermore, a long multi-step synthesis requires many hours of effort by the chemists conducting the reactions.

5. The format of a ___________ is important.

6. If numerous functional groups are present at intermediate stages, some of these may require protection from ________________.

7. The starting compounds and reagents for a synthesis must be purchased, so __________________ are often significant.

8. For a given target molecule, several different reaction sequences may serve to accomplish its ______________.

8 = ?

Drug Discovery

IMPORTANCE OF ORGANIC SYNTHESIS:

a. Vital for pharmaceuticals to develop new medicines.

b. Used in the creation of advanced materials.

c. Plays a role in developing new crop protection production.

a = ?

Materials Science

IMPORTANCE OF ORGANIC SYNTHESIS:

a. Vital for pharmaceuticals to develop new medicines.

b. Used in the creation of advanced materials.

c. Plays a role in developing new crop protection production.

b = ?

Agriculture

IMPORTANCE OF ORGANIC SYNTHESIS:

a. Vital for pharmaceuticals to develop new medicines.

b. Used in the creation of advanced materials.

c. Plays a role in developing new crop protection production.

c = ?

Selectivity

CHALLENGES IN ORGANIC SYNTHESIS

a. Ensuring reactions produce the desired product.

b. Maximizing the amount of product obtained.

c. EfficiencyMinimizing resource and time consumption.

a = ?

Yield

CHALLENGES IN ORGANIC SYNTHESIS

a. Ensuring reactions produce the desired product.

b. Maximizing the amount of product obtained.

c. EfficiencyMinimizing resource and time consumption.

b = ?

Efficiency

CHALLENGES IN ORGANIC SYNTHESIS

a. Ensuring reactions produce the desired product.

b. Maximizing the amount of product obtained.

c. EfficiencyMinimizing resource and time consumption.

c = ?

C9H8O4

molecular formula of Aspirin

2-acetoxybenzoic acid

IUPAC name of Aspirin

Acetylsalicyclic acid (ASA)

trivial name of aspirin

180.16 g/mol

molecular weight of aspirin

Aspirin

• odorless, white crystalline powder

• weak acid that is only slightly soluble in water, and slightly bitter taste

• known analgesic, antipyretic, anti-inflammatory drug

ester

Aspirin is an aromatic compound with carboxylic acid and _________ functional group

0.25g/100 mL @ 15 C

solubility of aspirin in water

1.40 g/cm³

density of aspirin

irritant

chemical safety of aspirin

hydrolyzes into salicylic acid and acetic acid

stability of aspirin: gradually _________________ upon exposure to moisture in air

benzene with an attached carboxyl group and ester group on ortho position

structure of aspirin:

cyclooxygenase (COX)

Mechanism of Action of Aspirin:

1. It works by inhibiting the enzyme ____________________, which is involved in the biosynthesis of prostaglandins compounds that mediate inflammation, pain, and fever.

2. By inhibiting it, aspirin reduces the production of ____________, thereby alleviating symptoms.

3. At low-doses, it has been found to have ____________ (prevent the formation of blood clots), making it valuable in the prevention of cardiovascular events such as heart attacks and strokes.

1 = ?

prostaglandins

Mechanism of Action of Aspirin:

1. It works by inhibiting the enzyme ____________________, which is involved in the biosynthesis of prostaglandins compounds that mediate inflammation, pain, and fever.

2. By inhibiting it, aspirin reduces the production of ____________, thereby alleviating symptoms.

3. At low-doses, it has been found to have ____________ (prevent the formation of blood clots), making it valuable in the prevention of cardiovascular events such as heart attacks and strokes.

2 = ?

antiplatelet effects

Mechanism of Action of Aspirin:

1. It works by inhibiting the enzyme ____________________, which is involved in the biosynthesis of prostaglandins compounds that mediate inflammation, pain, and fever.

2. By inhibiting it, aspirin reduces the production of ____________, thereby alleviating symptoms.

3. At low-doses, it has been found to have ____________ (prevent the formation of blood clots), making it valuable in the prevention of cardiovascular events such as heart attacks and strokes.

3 = ?

Acetylation (Esterification)

Type of reaction involved in production of:

• ______________ of salicylic acid with acetic anhydride

Felix Hoffmann (1897)

who synthesized aspirin in a German Pharmaceutical Company, Bayer?

30 minutes to 2 hours

Absorption: Aspirin is rapidly absorbed from the gastrointestinal tract, with peak plasma concentrations typically occurring within _____________ post-administration

plasma proteins

Distribution: Aspirin and its primary metabolite, salicylic acid, are widely distributed throughout the body. Salicylic acid is extensively bound to ___________, which can affect its pharmacokinetics and interactions with other drugs.

liver

Metabolism: After absorption, aspirin is hydrolyzed to salicylic acid in the a.______. Salicylic acid undergoes further metabolism through conjugation with b._________.

a = ?

glycine or glucuronic acid

Metabolism: After absorption, aspirin is hydrolyzed to salicylic acid in the a.______. Salicylic acid undergoes further metabolism through conjugation with b._________.

b = ?

kidneys

Excretion: The metabolites of aspirin are excreted primarily via the a._________. The elimination half-life of salicylic acid is b.__________, ranging from 2 to 19 hours, depending on the administered dose and individual metabolic variations.

a = ?

dose-dependent

Excretion: The metabolites of aspirin are excreted primarily via the a._________. The elimination half-life of salicylic acid is b.__________, ranging from 2 to 19 hours, depending on the administered dose and individual metabolic variations.

b = ?

Aspirin Toxicity (Salicylate poisoning)

Toxicology:

a. can occur with acute overdose or chronic high-dose administration. Symptoms include nausea, vomiting, tinnitus, hyperventilation, metabolic acidosis, and in severe cases, CNS effects like confusion and seizures.

b. occurs with chronic use

c. in specific populations such as children and adolescents with viral infections which can cause liver and brain damage

a = ?

Gastrointestinal ulcers and bleeding

Toxicology:

a. can occur with acute overdose or chronic high-dose administration. Symptoms include nausea, vomiting, tinnitus, hyperventilation, metabolic acidosis, and in severe cases, CNS effects like confusion and seizures.

b. occurs with chronic use

c. in specific populations such as children and adolescents with viral infections which can cause liver and brain damage

b = ?

Reye’s Syndrome

Toxicology:

a. can occur with acute overdose or chronic high-dose administration. Symptoms include nausea, vomiting, tinnitus, hyperventilation, metabolic acidosis, and in severe cases, CNS effects like confusion and seizures.

b. occurs with chronic use

c. in specific populations such as children and adolescents with viral infections which can cause liver and brain damage

c = ?

3.0 grams of salicylic acid

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

1 = ?

6 mL acetic anhydride

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

2 = ?

Gently stir

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

3 = ?

1 mL of concentrated phosphoric acid

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

4 = ?

15 mins

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

5 = ?

10-20 drops of ice-cold water

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

6 = ?

room temperature

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

7 = ?

less than 10-mL ice-cold distilled water

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

8 = ?

Buchner funnel

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

9 = ?

FeCl3

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

9.a. = ?

positive (blue-violet)

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

9.b. = ?

percentage yield

Procedure of Aspirin Synthesis:

1. Add ________________ in a 25 mL Erlenmeyer flask.

2. With constant stirring, add ______________________ (IRRITANT)

3. _______________ the mixture until all the salicylic acid dissolves.

4. Add carefully, __________________________________ (CORROSIVE). Take note of the rise in temperature of the reaction mixture.

5. Heat the reaction mixture in a boiling water bath for _________.

6. After heating, add ______________________________and observe precipitation of the crude ASA.

7. Let the mixture cool to ____________________.

8. Add __________________________________ to the cooled mixture.

9. Separate the crystals formed using a _______________ and wash with ice-cold distilled water.

a. Using the collected filtrate, test for the presence of unreacted salicylic acid by adding a few drops of ____________.

If the sample test ______________, perform recrystallization using benzene or ethyl acetate

10. Air-dry the product and weigh. Calculate the ___________________________.

10 = ?

acetic acid

by-product of Aspirin Synthesis

carbonyl oxygen of acetic anhydride

The esterification of salicylic acid and acid anhydride is catalyzed by a strong acid in order to protonate the _________________________, making it more electrophilic.

65:30:5 mixture of hexane, ethyl acetate and acetic acid

Mobile Phase of TLC for Aspirin

TLC

Stationary Phase of Aspirin Characterization

Short and Long Wave UV Light

visualization of aspirin in TLC

135 degrees C

Melting Point of Aspirin

Salicylic acid (limiting material) + Acetic Anhydride

reagents for the synthesis of aspirin

ester

functional group of aspirin