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25. Complete the following reaction with the major organic product(s) and provide a detailed mechanism for the following reaction. Include contributing resonance structures and the resonance hybrid for the arenium ion intermediates. (CH3)½CHCH,CH2CI AICI3 NO2

25. Complete the following reaction with the major organic product(s) and provide a detailed mechanism for the following reaction. Include contributing resonance structures and the resonance hybrid for the arenium ion intermediates. (CH3)½CHCH,CH2CI AICI3 NO2

Chemistry
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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### Reaction Mechanism Explanation for an Educational Website **Problem Statement:** Complete the following reaction with the major organic product(s) and provide a detailed mechanism for the following reaction. Include contributing resonance structures and the resonance hybrid for the arenium ion intermediates. **Reaction Details:** The reaction involves an aromatic compound with a nitro group (NO₂) substituent undergoing an electrophilic substitution reaction. The reagents used are (CH₃)₂CHCH₂CH₂Cl and AlCl₃. **Mechanism Overview:** 1. **Formation of the Electrophile:** - The alkyl chloride, (CH₃)₂CHCH₂CH₂Cl, reacts with aluminum chloride (AlCl₃) to form a highly reactive carbocation. The chlorine atom donates its electron pair to AlCl₃, resulting in the generation of a secondary carbocation, (CH₃)₂CHCH₂CH₂⁺. 2. **Formation of the Arenium Ion:** - The generated carbocation acts as an electrophile and attacks the electron-rich aromatic ring. This leads to the formation of an arenium ion (also known as a sigma complex). The positive charge can be delocalized over the ortho and para positions relative to the nitro group, resulting in several resonance structures. 3. **Resonance Structures:** - The arenium ion intermediate can be represented by different resonance structures, where the positive charge shifts to different carbon atoms around the ring. This delocalization stabilizes the intermediate. 4. **Deprotonation and Restoration of Aromaticity:** - A hydrogen atom is removed from the carbon atom bearing the new substituent, allowing the reformation of the π bond and restoring the aromaticity of the benzene ring. This step is typically facilitated by a base such as Cl⁻, which abstracts the proton. 5. **Formation of the Major Product:** - Depending on directing effects and sterics, the alkylation usually occurs at a position that stabilizes the arenium ion best, often ortho or para to existing substituents. **Conclusion:** This Friedel–Crafts alkylation process results in the substitution of the alkyl group onto the aromatic ring, forming the major organic product with potential regioisomers. Resonance structures showcase the electron delocalization that stabilizes intermediates during the reaction.
Transcribed Image Text:### Reaction Mechanism Explanation for an Educational Website **Problem Statement:** Complete the following reaction with the major organic product(s) and provide a detailed mechanism for the following reaction. Include contributing resonance structures and the resonance hybrid for the arenium ion intermediates. **Reaction Details:** The reaction involves an aromatic compound with a nitro group (NO₂) substituent undergoing an electrophilic substitution reaction. The reagents used are (CH₃)₂CHCH₂CH₂Cl and AlCl₃. **Mechanism Overview:** 1. **Formation of the Electrophile:** - The alkyl chloride, (CH₃)₂CHCH₂CH₂Cl, reacts with aluminum chloride (AlCl₃) to form a highly reactive carbocation. The chlorine atom donates its electron pair to AlCl₃, resulting in the generation of a secondary carbocation, (CH₃)₂CHCH₂CH₂⁺. 2. **Formation of the Arenium Ion:** - The generated carbocation acts as an electrophile and attacks the electron-rich aromatic ring. This leads to the formation of an arenium ion (also known as a sigma complex). The positive charge can be delocalized over the ortho and para positions relative to the nitro group, resulting in several resonance structures. 3. **Resonance Structures:** - The arenium ion intermediate can be represented by different resonance structures, where the positive charge shifts to different carbon atoms around the ring. This delocalization stabilizes the intermediate. 4. **Deprotonation and Restoration of Aromaticity:** - A hydrogen atom is removed from the carbon atom bearing the new substituent, allowing the reformation of the π bond and restoring the aromaticity of the benzene ring. This step is typically facilitated by a base such as Cl⁻, which abstracts the proton. 5. **Formation of the Major Product:** - Depending on directing effects and sterics, the alkylation usually occurs at a position that stabilizes the arenium ion best, often ortho or para to existing substituents. **Conclusion:** This Friedel–Crafts alkylation process results in the substitution of the alkyl group onto the aromatic ring, forming the major organic product with potential regioisomers. Resonance structures showcase the electron delocalization that stabilizes intermediates during the reaction.
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