Pigure 28: 7-hydroxy-4-methylcoumarin Synthesis from Resorcinol & Ethyl Acetoacetate Amberlyst-15 HO HO, OEt toluene HO

Chemistry
10th Edition
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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1. Draw the mechanism for this reaction

**Figure 28: 7-hydroxy-4-methylcoumarin Synthesis from Resorcinol & Ethyl Acetoacetate**

The image shows a chemical reaction for synthesizing 7-hydroxy-4-methylcoumarin. The reaction involves the following components:

- **Reactants:**
  - Resorcinol (Chemical structure: a benzene ring with two hydroxyl groups at positions 1 and 3)
  - Ethyl acetoacetate (Chemical structure: a ketone group adjacent to an ester group)

- **Conditions:**
  - **Amberlyst-15**: A catalyst used in the reaction
  - **Toluene**: Used as the solvent

- **Product:**
  - 7-hydroxy-4-methylcoumarin (Chemical structure: a benzene ring fused with a pyrone ring, hydroxyl group at position 7)

**Pre-Lab Questions:**

- Draw the mechanism for this reaction.

**Explanation:**

This reaction is typically a Pechmann condensation, an organic reaction to synthesize coumarins. The page instructs students to draw the detailed mechanism, illustrating the electron movement and intermediate structures involved during the synthesis process.
Transcribed Image Text:**Figure 28: 7-hydroxy-4-methylcoumarin Synthesis from Resorcinol & Ethyl Acetoacetate** The image shows a chemical reaction for synthesizing 7-hydroxy-4-methylcoumarin. The reaction involves the following components: - **Reactants:** - Resorcinol (Chemical structure: a benzene ring with two hydroxyl groups at positions 1 and 3) - Ethyl acetoacetate (Chemical structure: a ketone group adjacent to an ester group) - **Conditions:** - **Amberlyst-15**: A catalyst used in the reaction - **Toluene**: Used as the solvent - **Product:** - 7-hydroxy-4-methylcoumarin (Chemical structure: a benzene ring fused with a pyrone ring, hydroxyl group at position 7) **Pre-Lab Questions:** - Draw the mechanism for this reaction. **Explanation:** This reaction is typically a Pechmann condensation, an organic reaction to synthesize coumarins. The page instructs students to draw the detailed mechanism, illustrating the electron movement and intermediate structures involved during the synthesis process.
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