a. Propose an electron pushing mechanism for the conversion of o-phenylene diamine plus formic acid to the first amide intermediate (catalyzed by acid). Indicate all resonance stabilized carbocations with the letters "RSCC"

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### Organic Chemistry Exercise: Mechanisms and Yield Calculation

#### a. Electron Pushing Mechanism for Conversion

- **Task**: Propose an electron pushing mechanism for the conversion of o-phenylenediamine plus formic acid to the first amide intermediate, catalyzed by acid.
- **Instructions**: Indicate all resonance-stabilized carbocations with the letters "RSCC".

#### b. Cyclization to Benzimidazole

- **Task**: Propose an electron pushing mechanism for the cyclization of the amide intermediate to benzimidazole.
- **Instructions**: Indicate all resonance-stabilized carbocations with the letters "RSCC".

#### c. Calculate Mmol and Yield

- **Task**: Determine the mmol of both starting materials. Consider that formic acid is not pure but is 88% weight/volume, or 88g/100ml. Show your work.
- **Instructions**: Determine the limiting reagent in this synthesis. Lastly, calculate the theoretical yield of benzimidazole that you could expect to form.
Transcribed Image Text:### Organic Chemistry Exercise: Mechanisms and Yield Calculation #### a. Electron Pushing Mechanism for Conversion - **Task**: Propose an electron pushing mechanism for the conversion of o-phenylenediamine plus formic acid to the first amide intermediate, catalyzed by acid. - **Instructions**: Indicate all resonance-stabilized carbocations with the letters "RSCC". #### b. Cyclization to Benzimidazole - **Task**: Propose an electron pushing mechanism for the cyclization of the amide intermediate to benzimidazole. - **Instructions**: Indicate all resonance-stabilized carbocations with the letters "RSCC". #### c. Calculate Mmol and Yield - **Task**: Determine the mmol of both starting materials. Consider that formic acid is not pure but is 88% weight/volume, or 88g/100ml. Show your work. - **Instructions**: Determine the limiting reagent in this synthesis. Lastly, calculate the theoretical yield of benzimidazole that you could expect to form.
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