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Outline an acceptable step by step mechanism for the Nucleophilic aromatic substitution of ortho-fluoronitrobenzene with methylamine. Do not forget to include the formal charges of all non-hydrogen atoms that do not have a neutral charge. F CH,NH, NO2 (excess)

Outline an acceptable step by step mechanism for the Nucleophilic aromatic substitution of ortho-fluoronitrobenzene with methylamine. Do not forget to include the formal charges of all non-hydrogen atoms that do not have a neutral charge. F CH,NH, NO2 (excess)

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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
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3) Outline an acceptable step by step mechanism for the Nucleophilic aromatic substitution of ortho-fluoronitrobenzene with methylamine.  Do not forget to include the formal charges of all non-hydrogen atoms that do not have a neutral charge. 

**Nucleophilic Aromatic Substitution Mechanism of Ortho-fluoronitrobenzene with Methylamine** **Problem Statement:** Outline an acceptable step-by-step mechanism for the nucleophilic aromatic substitution of ortho-fluoronitrobenzene with methylamine. Do not forget to include the formal charges of all non-hydrogen atoms that do not have a neutral charge. **Reaction Scheme:** Reactants: - Ortho-fluoronitrobenzene (benzene ring with a fluorine atom and nitro group attached at the ortho positions) - CH₃NH₂ (methylamine) in excess **Detailed Explanation:** 1. **Nucleophilic Attack:** - Methylamine (CH₃NH₂) acts as a nucleophile and attacks the carbon atom bonded to the fluorine atom (C-F bond) in ortho-fluoronitrobenzene. - The presence of the nitro group (NO₂) as an electron-withdrawing group stabilizes the intermediate by delocalizing the negative charge. 2. **Formation of Meisenheimer Complex:** - A Meisenheimer complex (a negatively charged intermediate) is formed where the fluorine atom is still attached. - This complex has an intermediate structure where the negative charge is delocalized over the ortho and para positions relative to the nitro group. 3. **Departure of Leaving Group:** - The fluorine atom (F^-) leaves as a fluoride ion, restoring the aromaticity of the benzene ring. - This step results in the substitution of the fluorine atom by the methylamine group. 4. **Restoration of Aromaticity:** - The final product is a benzene ring with the methylamine group (NHCH₃) positioned ortho to the nitro group (NO₂). **Formal Charges:** - The methylamine nitrogen (NH₃) does not have a formal charge in the final product. - The nitro group (NO₂) has a resonance structure where one oxygen carries a negative charge, and the nitrogen carries a positive charge. **Diagram Explanation:** - There is an illustration with a benzene ring showing a fluorine atom (F) and a nitro group (NO₂) attached to it. - An arrow points towards CH₃NH₂ (methylamine) indicating
Transcribed Image Text:**Nucleophilic Aromatic Substitution Mechanism of Ortho-fluoronitrobenzene with Methylamine** **Problem Statement:** Outline an acceptable step-by-step mechanism for the nucleophilic aromatic substitution of ortho-fluoronitrobenzene with methylamine. Do not forget to include the formal charges of all non-hydrogen atoms that do not have a neutral charge. **Reaction Scheme:** Reactants: - Ortho-fluoronitrobenzene (benzene ring with a fluorine atom and nitro group attached at the ortho positions) - CH₃NH₂ (methylamine) in excess **Detailed Explanation:** 1. **Nucleophilic Attack:** - Methylamine (CH₃NH₂) acts as a nucleophile and attacks the carbon atom bonded to the fluorine atom (C-F bond) in ortho-fluoronitrobenzene. - The presence of the nitro group (NO₂) as an electron-withdrawing group stabilizes the intermediate by delocalizing the negative charge. 2. **Formation of Meisenheimer Complex:** - A Meisenheimer complex (a negatively charged intermediate) is formed where the fluorine atom is still attached. - This complex has an intermediate structure where the negative charge is delocalized over the ortho and para positions relative to the nitro group. 3. **Departure of Leaving Group:** - The fluorine atom (F^-) leaves as a fluoride ion, restoring the aromaticity of the benzene ring. - This step results in the substitution of the fluorine atom by the methylamine group. 4. **Restoration of Aromaticity:** - The final product is a benzene ring with the methylamine group (NHCH₃) positioned ortho to the nitro group (NO₂). **Formal Charges:** - The methylamine nitrogen (NH₃) does not have a formal charge in the final product. - The nitro group (NO₂) has a resonance structure where one oxygen carries a negative charge, and the nitrogen carries a positive charge. **Diagram Explanation:** - There is an illustration with a benzene ring showing a fluorine atom (F) and a nitro group (NO₂) attached to it. - An arrow points towards CH₃NH₂ (methylamine) indicating
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