The following reaction is Friedel-Crafts alkylation. Considering the mechanism for Friedel-Crafts alkylation, how would you explain the formation of this particular product? Either describe or upload image of the mechanism. AICI,
The following reaction is Friedel-Crafts alkylation. Considering the mechanism for Friedel-Crafts alkylation, how would you explain the formation of this particular product? Either describe or upload image of the mechanism. AICI,
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![### Friedel-Crafts Alkylation Mechanism
#### Introduction
The following example illustrates the Friedel-Crafts alkylation reaction. In Friedel-Crafts alkylation, an alkyl group is introduced to an aromatic ring through the reaction of an alkyl chloride with a Lewis acid catalyst, such as aluminum chloride (AlCl₃).
#### Reaction Overview
**Reactants:**
1. Benzene (C₆H₆)
2. 1-Chlorobutane (C₄H₉Cl)
**Catalyst:**
- Aluminum chloride (AlCl₃)
**Product:**
- sec-Butylbenzene
**General Reaction:**
\[ \text{Benzene} + \text{1-Chlorobutane} \xrightarrow{\text{AlCl}_{3}} \text{sec-Butylbenzene} \]
#### Mechanism Explanation
The reaction proceeds through a multi-step mechanism, which can be outlined as follows:
1. **Formation of Carbocation:**
- Aluminum chloride (AlCl₃), a strong Lewis acid, interacts with 1-chlorobutane to form a butyl carbocation and the complex AlCl₄⁻.
\[ \text{C₄H₉Cl} + \text{AlCl₃} \rightarrow (\text{CH₃CH₂CH₂CH}_{2}^{+}) + \text{AlCl₄⁻} \]
2. **Generation of the Electrophile:**
- The generated sec-butyl carbocation (\(\text{CH₃CHCH₂}^{+}\text{CH₃}\)) serves as a highly reactive electrophile.
3. **Electrophilic Aromatic Substitution:**
- This carbocation then attacks the electron-rich benzene ring, forming a sigma complex (also known as the arenium ion).
\[ \text{Benzene} + \text{sec-Butyl carbocation} \rightarrow \text{Cyclohexadienyl cation} \]
4. **Regeneration of Aromaticity:**
- Finally, the complex loses a proton (H⁺) to regenerate the aromatic system, forming sec-butylbenzene as the major product.
#### Diagram Explanation
- **Left Side:** The reactants, including benzene and 1-chlorobutane with a visible](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fef4f72d3-80ca-49e0-beb6-c5f7f04e690f%2Fce1021ff-28cc-4af7-aa16-c2ed63c94491%2Fz353bej_processed.png&w=3840&q=75)
Transcribed Image Text:### Friedel-Crafts Alkylation Mechanism
#### Introduction
The following example illustrates the Friedel-Crafts alkylation reaction. In Friedel-Crafts alkylation, an alkyl group is introduced to an aromatic ring through the reaction of an alkyl chloride with a Lewis acid catalyst, such as aluminum chloride (AlCl₃).
#### Reaction Overview
**Reactants:**
1. Benzene (C₆H₆)
2. 1-Chlorobutane (C₄H₉Cl)
**Catalyst:**
- Aluminum chloride (AlCl₃)
**Product:**
- sec-Butylbenzene
**General Reaction:**
\[ \text{Benzene} + \text{1-Chlorobutane} \xrightarrow{\text{AlCl}_{3}} \text{sec-Butylbenzene} \]
#### Mechanism Explanation
The reaction proceeds through a multi-step mechanism, which can be outlined as follows:
1. **Formation of Carbocation:**
- Aluminum chloride (AlCl₃), a strong Lewis acid, interacts with 1-chlorobutane to form a butyl carbocation and the complex AlCl₄⁻.
\[ \text{C₄H₉Cl} + \text{AlCl₃} \rightarrow (\text{CH₃CH₂CH₂CH}_{2}^{+}) + \text{AlCl₄⁻} \]
2. **Generation of the Electrophile:**
- The generated sec-butyl carbocation (\(\text{CH₃CHCH₂}^{+}\text{CH₃}\)) serves as a highly reactive electrophile.
3. **Electrophilic Aromatic Substitution:**
- This carbocation then attacks the electron-rich benzene ring, forming a sigma complex (also known as the arenium ion).
\[ \text{Benzene} + \text{sec-Butyl carbocation} \rightarrow \text{Cyclohexadienyl cation} \]
4. **Regeneration of Aromaticity:**
- Finally, the complex loses a proton (H⁺) to regenerate the aromatic system, forming sec-butylbenzene as the major product.
#### Diagram Explanation
- **Left Side:** The reactants, including benzene and 1-chlorobutane with a visible
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