Mechanism. Provide the complete mechanism for the reaction below. You must include appropriate arrows, intermediates, and formal charges. OH of ll of OH NH NH₂ 2. Heat

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**Mechanism Explanation:**

The reaction involves the transformation of a carboxylic acid derivative of an aromatic compound into an amide. The starting material is a benzoic acid derivative containing an amino group (–NH₂) ortho to the carboxylic acid group.

**Reaction Components:**

1. **Reactants:**
   - The starting compound is 2-aminobenzoic acid.
   - Acetic anhydride (represented by two carbonyl groups connected by an oxygen atom) is used as a reagent.

2. **Reaction Conditions:**
   - Heat is applied to facilitate the reaction.

**Mechanistic Steps:**

1. **Nucleophilic Attack:**
   - The amino group (–NH₂) on the benzoic acid acts as a nucleophile and attacks the carbonyl carbon of acetic anhydride. This step involves the formation of a tetrahedral intermediate.

2. **Formation of Amide Bond:**
   - The tetrahedral intermediate collapses, expelling a leaving group (acetate ion, CH₃COO⁻) from acetic anhydride, leading to the formation of an amide linkage (–NH–C(=O)CH₃).

3. **Cyclization:**
   - Heat facilitates cyclization, where the newly formed amide bond allows the aromatic system to regain aromaticity by eliminating water (H₂O), forming a stable cyclic amide.

**Final Product:**

- The product is an amide where the former amino group is now attached to the carbonyl of acetic anhydride, forming a cyclic compound. The hydroxyl group (–OH) on the aromatic ring remains unchanged.

This mechanism illustrates the common acylation transformation utilizing acetic anhydride, resulting in a cyclic amide product from an ortho-amino benzoic acid derivative.
Transcribed Image Text:**Mechanism Explanation:** The reaction involves the transformation of a carboxylic acid derivative of an aromatic compound into an amide. The starting material is a benzoic acid derivative containing an amino group (–NH₂) ortho to the carboxylic acid group. **Reaction Components:** 1. **Reactants:** - The starting compound is 2-aminobenzoic acid. - Acetic anhydride (represented by two carbonyl groups connected by an oxygen atom) is used as a reagent. 2. **Reaction Conditions:** - Heat is applied to facilitate the reaction. **Mechanistic Steps:** 1. **Nucleophilic Attack:** - The amino group (–NH₂) on the benzoic acid acts as a nucleophile and attacks the carbonyl carbon of acetic anhydride. This step involves the formation of a tetrahedral intermediate. 2. **Formation of Amide Bond:** - The tetrahedral intermediate collapses, expelling a leaving group (acetate ion, CH₃COO⁻) from acetic anhydride, leading to the formation of an amide linkage (–NH–C(=O)CH₃). 3. **Cyclization:** - Heat facilitates cyclization, where the newly formed amide bond allows the aromatic system to regain aromaticity by eliminating water (H₂O), forming a stable cyclic amide. **Final Product:** - The product is an amide where the former amino group is now attached to the carbonyl of acetic anhydride, forming a cyclic compound. The hydroxyl group (–OH) on the aromatic ring remains unchanged. This mechanism illustrates the common acylation transformation utilizing acetic anhydride, resulting in a cyclic amide product from an ortho-amino benzoic acid derivative.
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