
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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![**Step-by-Step Organic Chemistry Mechanism: Friedel-Crafts Alkylation**
**Question 18.49d1:**
*Task: Draw Step 1 of the Mechanism for the Following Transformation*
**Transformation Description:**
For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogens explicitly in your products. Do not use abbreviations such as Me or Ph.
**Reaction Overview:**
\[ \text{Benzene} \xrightarrow{\text{CH}_3\text{Cl}, \text{AlCl}_3} \text{Toluene} \]
**Step 1:**
In this step, you will initiate the Friedel-Crafts alkylation by forming the electrophile.
### Reactants:
1. methyl chloride (CH₃-Cl)
2. aluminum chloride (AlCl₃)
### Diagram:
*On the left side:*
- Show the structure of methyl chloride.
- Show the structure of aluminum chloride.
**Diagram Explanation:**
1. **Methyl Chloride (CH₃-Cl)**:
- The molecule is represented with a CH₃ group bonded to a Cl atom.
2. **Aluminum Chloride (AlCl₃)**:
- This is a Lewis acid, represented with an Al atom bonded to three Cl atoms.
3. **Formation of Electrophile**:
- Illustrate the interaction between the lone pair of electrons on the chlorine atom (CH₃-Cl) and the aluminum atom (AlCl₃).
**Instructions for Drawing:**
- Draw the curved arrows indicating the movement of electrons from the chlorine atom to the aluminum atom.
- Depict the formation of the complex, where AlCl₃ coordinates with CH₃-Cl.
**Begin Drawing** (using the edit drawing tool provided in the interface):
\[ \text{CH}_3\text{-Cl} + \text{AlCl}_3 \rightarrow [\text{CH}_3^+- \ \ \ \ \text{Cl-AlCl}_3^-] \arrow \]
By following these steps and correctly drawing the reaction mechanism, you'll outline the initial step of the Friedel-Crafts alkylation reaction, focusing on the formation of the electrophile. This will set the stage for the alkylation of benzene to form toluene in subsequent steps.](https://content.bartleby.com/qna-images/question/233396bf-72f6-4e47-8d0d-be3130c6d58a/f68315e1-0d85-4ac8-944f-31cdc4f90a60/7zfloqp_thumbnail.jpeg)
Transcribed Image Text:**Step-by-Step Organic Chemistry Mechanism: Friedel-Crafts Alkylation**
**Question 18.49d1:**
*Task: Draw Step 1 of the Mechanism for the Following Transformation*
**Transformation Description:**
For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogens explicitly in your products. Do not use abbreviations such as Me or Ph.
**Reaction Overview:**
\[ \text{Benzene} \xrightarrow{\text{CH}_3\text{Cl}, \text{AlCl}_3} \text{Toluene} \]
**Step 1:**
In this step, you will initiate the Friedel-Crafts alkylation by forming the electrophile.
### Reactants:
1. methyl chloride (CH₃-Cl)
2. aluminum chloride (AlCl₃)
### Diagram:
*On the left side:*
- Show the structure of methyl chloride.
- Show the structure of aluminum chloride.
**Diagram Explanation:**
1. **Methyl Chloride (CH₃-Cl)**:
- The molecule is represented with a CH₃ group bonded to a Cl atom.
2. **Aluminum Chloride (AlCl₃)**:
- This is a Lewis acid, represented with an Al atom bonded to three Cl atoms.
3. **Formation of Electrophile**:
- Illustrate the interaction between the lone pair of electrons on the chlorine atom (CH₃-Cl) and the aluminum atom (AlCl₃).
**Instructions for Drawing:**
- Draw the curved arrows indicating the movement of electrons from the chlorine atom to the aluminum atom.
- Depict the formation of the complex, where AlCl₃ coordinates with CH₃-Cl.
**Begin Drawing** (using the edit drawing tool provided in the interface):
\[ \text{CH}_3\text{-Cl} + \text{AlCl}_3 \rightarrow [\text{CH}_3^+- \ \ \ \ \text{Cl-AlCl}_3^-] \arrow \]
By following these steps and correctly drawing the reaction mechanism, you'll outline the initial step of the Friedel-Crafts alkylation reaction, focusing on the formation of the electrophile. This will set the stage for the alkylation of benzene to form toluene in subsequent steps.
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