4. You may know salicylic acid as an ingredient in anti-acne medication, or as a precursor to aspirin. Salicylic acid is also synthesized by the following reaction: ONa OH you 1. CO₂, heat 2. H₂O* a. Draw a reasonable arrow-pushing mechanism for the formation of the product. b. The challenge: Reach back to 2311 or general chemistry to propose why the ortho position is favored over para for this product.

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Chapter1: Chemical Foundations
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**4.** You may know salicylic acid as an ingredient in anti-acne medication, or as a precursor to aspirin.

**Salicylic acid is also synthesized by the following reaction:**

A diagram is shown depicting a chemical reaction. The reactant is sodium phenoxide (a benzene ring with an attached sodium group as O⁻Na⁺). Above the reaction arrow, two conditions are given: 

1. CO₂, heat
2. H₃O⁺

The product is salicylic acid (a benzene ring with an attached hydroxyl group (OH) and a carboxylic acid group (COOH) ortho to each other).

**a.** Draw a reasonable arrow-pushing mechanism for the formation of the product.

**b.** The challenge: Reach back to 2311 or general chemistry to propose why the *ortho* position is favored over *para* for this product.

---

**Explanation of Diagram:**

The chemical diagram illustrates a synthetic route for producing salicylic acid through the process of Kolbe-Schmitt reaction. In the first step, sodium phenoxide reacts with carbon dioxide under heat, likely forming a carboxylation intermediate. The second step involves acidification with H₃O⁺ to form salicylic acid. The specific positions of substituents on the benzene ring are outlined, emphasizing the ortho relationship in the final product.

These types of reactions are important in organic synthesis, especially for pharmaceuticals and materials science.

---
Transcribed Image Text:Certainly! Here's the transcription and explanation suitable for an educational website: --- **4.** You may know salicylic acid as an ingredient in anti-acne medication, or as a precursor to aspirin. **Salicylic acid is also synthesized by the following reaction:** A diagram is shown depicting a chemical reaction. The reactant is sodium phenoxide (a benzene ring with an attached sodium group as O⁻Na⁺). Above the reaction arrow, two conditions are given: 1. CO₂, heat 2. H₃O⁺ The product is salicylic acid (a benzene ring with an attached hydroxyl group (OH) and a carboxylic acid group (COOH) ortho to each other). **a.** Draw a reasonable arrow-pushing mechanism for the formation of the product. **b.** The challenge: Reach back to 2311 or general chemistry to propose why the *ortho* position is favored over *para* for this product. --- **Explanation of Diagram:** The chemical diagram illustrates a synthetic route for producing salicylic acid through the process of Kolbe-Schmitt reaction. In the first step, sodium phenoxide reacts with carbon dioxide under heat, likely forming a carboxylation intermediate. The second step involves acidification with H₃O⁺ to form salicylic acid. The specific positions of substituents on the benzene ring are outlined, emphasizing the ortho relationship in the final product. These types of reactions are important in organic synthesis, especially for pharmaceuticals and materials science. ---
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