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Reaction Scheme: y NO ON-OH oso3H -ÕH₂ HSO4 8 O=NO Betu H- HSO4 OCH3 O₂N nitronium OCH3 OCH3

Reaction Scheme: y NO ON-OH oso3H -ÕH₂ HSO4 8 O=NO Betu H- HSO4 OCH3 O₂N nitronium OCH3 OCH3

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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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Nitrating methyl benzoate. 1.Describe the mechanism of EAS clearly and in detail 2. What is the effect of subtituent of the outcome of EAS；include 3 classes of subtituents
### Reaction Scheme: This image illustrates a multi-step chemical reaction involving the formation of a nitronium ion and its subsequent reaction with an aromatic compound. 1. **Formation of Nitronium Ion:** - The reaction begins with nitric acid (HNO₃) interacting with sulfuric acid (H₂SO₄). - A proton (H⁺) is transferred to nitric acid, resulting in the formation of a positively charged intermediate (H₂ONO₂⁺). - This intermediate undergoes rearrangement to form the nitronium ion (NO₂⁺), a key electrophile in this reaction. - The by-product of this step is bisulfate anion (HSO₄⁻). 2. **Nitration of an Aromatic Compound:** - The nitronium ion (NO₂⁺) then reacts with the aromatic compound methyl benzoate. - This involves the electrophilic attack of NO₂⁺ on the benzene ring, forming a sigma complex (arenium ion). - A proton (H⁺) is subsequently lost, facilitated by HSO₄⁻, to restore aromaticity. 3. **Final Product:** - The final product of this reaction is a nitrated aromatic compound, specifically, nitro methyl benzoate. This reaction scheme is a classic example of electrophilic aromatic nitration, commonly used in organic chemistry to introduce nitro groups into aromatic rings.
Transcribed Image Text:### Reaction Scheme: This image illustrates a multi-step chemical reaction involving the formation of a nitronium ion and its subsequent reaction with an aromatic compound. 1. **Formation of Nitronium Ion:** - The reaction begins with nitric acid (HNO₃) interacting with sulfuric acid (H₂SO₄). - A proton (H⁺) is transferred to nitric acid, resulting in the formation of a positively charged intermediate (H₂ONO₂⁺). - This intermediate undergoes rearrangement to form the nitronium ion (NO₂⁺), a key electrophile in this reaction. - The by-product of this step is bisulfate anion (HSO₄⁻). 2. **Nitration of an Aromatic Compound:** - The nitronium ion (NO₂⁺) then reacts with the aromatic compound methyl benzoate. - This involves the electrophilic attack of NO₂⁺ on the benzene ring, forming a sigma complex (arenium ion). - A proton (H⁺) is subsequently lost, facilitated by HSO₄⁻, to restore aromaticity. 3. **Final Product:** - The final product of this reaction is a nitrated aromatic compound, specifically, nitro methyl benzoate. This reaction scheme is a classic example of electrophilic aromatic nitration, commonly used in organic chemistry to introduce nitro groups into aromatic rings.
**Title: Understanding the Stability of Substituted Benzene Compounds** **Diagram Explanation:** The image illustrates the resonance structures resulting from the electrophilic aromatic substitution of a benzene ring that has an acetyl group (CH₃C=O) attached. The compound is subjected to a nitration reaction, with the incoming electrophile being the nitronium ion (NO₂⁺). **Reaction Pathways:** 1. **Ortho Position Reaction (o⁻):** - The nitronium ion attacks the ortho position relative to the acetyl group. - Multiple resonance structures are shown where positive charges appear at different carbon atoms. - The structure marked "Least stable" indicates destabilization due to a positive charge on the carbon bearing the electron-withdrawing acetyl group. 2. **Meta Position Reaction (m⁻):** - The nitronium ion attacks the meta position. - Resonance structures illustrate positive charges without involving the carbon bonded to the acetyl group directly, suggesting relative stability. 3. **Para Position Reaction (p⁻):** - The nitronium ion attacks the para position. - Similar to the ortho pathway, resonance forms indicate instability due to positive charge localization at the acetyl-bonded carbon, also marked as "Least stable." **Text Explanation:** **Why Meta Position is the Most Stable Form:** Electrophilic attack at either the ortho or para position places a positive charge on the carbon that bears the substituent (CH₃C=O). This charge placement directly on the carbon with an electron-withdrawing group (acetyl group) leads to decreased stability due to the electron deficiency being exacerbated. Conversely, in the meta attack, such unfavorable charge arrangements are avoided, leading to greater overall stability of the product. This conceptual illustration highlights the significance of position selection in enhancing the stability of compounds through electrophilic aromatic substitution.
Transcribed Image Text:**Title: Understanding the Stability of Substituted Benzene Compounds** **Diagram Explanation:** The image illustrates the resonance structures resulting from the electrophilic aromatic substitution of a benzene ring that has an acetyl group (CH₃C=O) attached. The compound is subjected to a nitration reaction, with the incoming electrophile being the nitronium ion (NO₂⁺). **Reaction Pathways:** 1. **Ortho Position Reaction (o⁻):** - The nitronium ion attacks the ortho position relative to the acetyl group. - Multiple resonance structures are shown where positive charges appear at different carbon atoms. - The structure marked "Least stable" indicates destabilization due to a positive charge on the carbon bearing the electron-withdrawing acetyl group. 2. **Meta Position Reaction (m⁻):** - The nitronium ion attacks the meta position. - Resonance structures illustrate positive charges without involving the carbon bonded to the acetyl group directly, suggesting relative stability. 3. **Para Position Reaction (p⁻):** - The nitronium ion attacks the para position. - Similar to the ortho pathway, resonance forms indicate instability due to positive charge localization at the acetyl-bonded carbon, also marked as "Least stable." **Text Explanation:** **Why Meta Position is the Most Stable Form:** Electrophilic attack at either the ortho or para position places a positive charge on the carbon that bears the substituent (CH₃C=O). This charge placement directly on the carbon with an electron-withdrawing group (acetyl group) leads to decreased stability due to the electron deficiency being exacerbated. Conversely, in the meta attack, such unfavorable charge arrangements are avoided, leading to greater overall stability of the product. This conceptual illustration highlights the significance of position selection in enhancing the stability of compounds through electrophilic aromatic substitution.
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