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  • Friedel-Crafts Acylation of Benzene with Acetyl Chloride: Mechanism & Products
    The reaction of benzene with CH3COCl (acetyl chloride) in the presence of AlCl3 is a classic example of Friedel-Crafts acylation. Here's what happens:

    1. Formation of the Electrophile:

    * AlCl3 is a Lewis acid and acts as a catalyst. It reacts with CH3COCl to form an electrophilic acylium ion (CH3CO+). This is the key step, as the acylium ion is the species that will attack the benzene ring.

    2. Electrophilic Attack:

    * The acylium ion is a strong electrophile. It attacks the electron-rich benzene ring, forming a carbocation intermediate. This step is the rate-determining step of the reaction.

    3. Rearrangement and Deprotonation:

    * The carbocation intermediate undergoes a resonance-stabilized rearrangement.

    * A proton (H+) is removed from the ring, regenerating the aromatic system.

    4. Regeneration of the Catalyst:

    * AlCl3 is regenerated and can continue to catalyze the reaction.

    Overall Reaction:

    ```

    Benzene + CH3COCl (AlCl3) --> Acetophenone + HCl

    ```

    Product:

    The final product of this reaction is acetophenone, a ketone with a phenyl group attached to the carbonyl group.

    Important Notes:

    * The reaction requires anhydrous conditions. Water will deactivate the catalyst (AlCl3) and prevent the reaction from proceeding.

    * The reaction is exothermic and can be violent if not carefully controlled.

    * Friedel-Crafts acylation is a versatile reaction that can be used to introduce a variety of acyl groups onto aromatic rings.

    Let me know if you have any more questions!

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