OMe OMe tert-Butanol H2SO4 Acetic acid OMe OMe

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
Chapter1: Chemical Foundations
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Draw the mechanism

### Electrophilic Aromatic Substitution Reaction

**Overview:**
The image depicts an example of an electrophilic aromatic substitution reaction, where a methoxy-substituted benzene compound undergoes an alkylation process.

**Reactants and Conditions:**
- **Starting Material**: A benzene ring with two methoxy groups (OMe) in para positions.
- **Reagents**: 
  - tert-Butanol (tertiary butanol)
  - Sulfuric Acid (H₂SO₄)
  - Acetic Acid as a solvent

**Reaction Mechanism:**
1. **tert-Butanol** acts as an alkylating agent. In the presence of sulfuric acid, it forms a carbocation.
2. The methoxy groups on the benzene ring are electron-donating groups that activate the ring towards electrophilic substitution.
3. The electrophilic tert-butyl carbocation attacks the para position with respect to the methoxy groups (already occupied by OMe groups), resulting in the formation of a new alkylated aromatic compound.

**Product:**
- **Final Compound**: A benzene ring with methoxy groups and a new tert-butyl group attached.

**Explanation of Diagrams:**
- **Left Structure**: The starting material (dimethoxybenzene).
- **Right Structure**: The product, showing the addition of the tert-butyl group.

This reaction is an example of how activating substituents on a benzene ring can direct further substitution to the ortho and para positions, following typical electrophilic aromatic substitution patterns.
Transcribed Image Text:### Electrophilic Aromatic Substitution Reaction **Overview:** The image depicts an example of an electrophilic aromatic substitution reaction, where a methoxy-substituted benzene compound undergoes an alkylation process. **Reactants and Conditions:** - **Starting Material**: A benzene ring with two methoxy groups (OMe) in para positions. - **Reagents**: - tert-Butanol (tertiary butanol) - Sulfuric Acid (H₂SO₄) - Acetic Acid as a solvent **Reaction Mechanism:** 1. **tert-Butanol** acts as an alkylating agent. In the presence of sulfuric acid, it forms a carbocation. 2. The methoxy groups on the benzene ring are electron-donating groups that activate the ring towards electrophilic substitution. 3. The electrophilic tert-butyl carbocation attacks the para position with respect to the methoxy groups (already occupied by OMe groups), resulting in the formation of a new alkylated aromatic compound. **Product:** - **Final Compound**: A benzene ring with methoxy groups and a new tert-butyl group attached. **Explanation of Diagrams:** - **Left Structure**: The starting material (dimethoxybenzene). - **Right Structure**: The product, showing the addition of the tert-butyl group. This reaction is an example of how activating substituents on a benzene ring can direct further substitution to the ortho and para positions, following typical electrophilic aromatic substitution patterns.
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