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ОН О CH3 H,SO4 cat. HO. + HO. + ОН salicylic acid m.w. 138.12 acetic anhydride m.w. 102.09 density 1.08 g/mL acetylsalicylic acid (aspirin) m.w. 180.15 acetic acid

ОН О CH3 H,SO4 cat. HO. + HO. + ОН salicylic acid m.w. 138.12 acetic anhydride m.w. 102.09 density 1.08 g/mL acetylsalicylic acid (aspirin) m.w. 180.15 acetic acid

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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The following reaction is an equilibrium; it’s reversible under the conditions to be used. Why will the product side be favored? What principle is at work? Explain.
### Esterification of Salicylic Acid to Produce Acetylsalicylic Acid (Aspirin) The reaction depicted above represents the synthesis of acetylsalicylic acid, commonly known as aspirin, through the esterification of salicylic acid with acetic anhydride. The process is catalyzed by sulfuric acid (\( \text{H}_2\text{SO}_4 \)). #### Reactants: 1. **Salicylic Acid** - Chemical Structure: Contains a benzene ring with a hydroxyl (\(-OH\)) group and a carboxylic acid group (\(-COOH\)). - Molecular Weight (m.w.): 138.12 g/mol 2. **Acetic Anhydride** - Chemical Structure: Two acetyl groups bonded to an oxygen atom. - Molecular Weight (m.w.): 102.09 g/mol - Density: 1.08 g/mL #### Catalyst: - **Sulfuric Acid (\( \text{H}_2\text{SO}_4 \))** #### Products: 1. **Acetylsalicylic Acid (Aspirin)** - Chemical Structure: Features an ester linkage formed between salicylic acid and acetic anhydride. - Molecular Weight (m.w.): 180.15 g/mol 2. **Acetic Acid** - Chemical Structure: Composed of a methyl group linked to a carboxyl group. ### Reaction Explanation: The reaction proceeds as salicylic acid reacts with acetic anhydride in the presence of a catalytic amount of sulfuric acid. This forms acetylsalicylic acid and acetic acid. The esterification involves the conversion of the hydroxyl group of salicylic acid into an ester group by the acetic anhydride, with acetic acid as a byproduct. This synthesis is a classic example of an acetylation reaction and is widely used in the pharmaceutical industry for the production of aspirin.
Transcribed Image Text:### Esterification of Salicylic Acid to Produce Acetylsalicylic Acid (Aspirin) The reaction depicted above represents the synthesis of acetylsalicylic acid, commonly known as aspirin, through the esterification of salicylic acid with acetic anhydride. The process is catalyzed by sulfuric acid (\( \text{H}_2\text{SO}_4 \)). #### Reactants: 1. **Salicylic Acid** - Chemical Structure: Contains a benzene ring with a hydroxyl (\(-OH\)) group and a carboxylic acid group (\(-COOH\)). - Molecular Weight (m.w.): 138.12 g/mol 2. **Acetic Anhydride** - Chemical Structure: Two acetyl groups bonded to an oxygen atom. - Molecular Weight (m.w.): 102.09 g/mol - Density: 1.08 g/mL #### Catalyst: - **Sulfuric Acid (\( \text{H}_2\text{SO}_4 \))** #### Products: 1. **Acetylsalicylic Acid (Aspirin)** - Chemical Structure: Features an ester linkage formed between salicylic acid and acetic anhydride. - Molecular Weight (m.w.): 180.15 g/mol 2. **Acetic Acid** - Chemical Structure: Composed of a methyl group linked to a carboxyl group. ### Reaction Explanation: The reaction proceeds as salicylic acid reacts with acetic anhydride in the presence of a catalytic amount of sulfuric acid. This forms acetylsalicylic acid and acetic acid. The esterification involves the conversion of the hydroxyl group of salicylic acid into an ester group by the acetic anhydride, with acetic acid as a byproduct. This synthesis is a classic example of an acetylation reaction and is widely used in the pharmaceutical industry for the production of aspirin.
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