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  • Aromatic Halogen

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    Ashila Nuraini
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    The document summarizes the halogenation of benzene through electrophilic aromatic substitution. Bromine reacts with a Lewis acid catalyst like iron(III) bromide to form an electrophilic bromonium ion. This attacks the pi electrons of benzene's aromatic carbon-carbon bonds. The resulting cyclohexadienyl cation loses a proton, reforming the aromatic system with a bromine atom substituted on the ring and regenerating the Lewis acid catalyst.

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    The document summarizes the halogenation of benzene through electrophilic aromatic substitution. Bromine reacts with a Lewis acid catalyst like iron(III) bromide to form an electrophilic bromonium ion. This attacks the pi electrons of benzene's aromatic carbon-carbon bonds. The resulting cyclohexadienyl cation loses a proton, reforming the aromatic system with a bromine atom substituted on the ring and regenerating the Lewis acid catalyst.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as DOCX, PDF, TXT or read online from Scribd
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    19 views1 page

    Aromatic Halogen

    Uploaded by

    Ashila Nuraini
    The document summarizes the halogenation of benzene through electrophilic aromatic substitution. Bromine reacts with a Lewis acid catalyst like iron(III) bromide to form an electrophilic bromonium ion. This attacks the pi electrons of benzene's aromatic carbon-carbon bonds. The resulting cyclohexadienyl cation loses a proton, reforming the aromatic system with a bromine atom substituted on the ring and regenerating the Lewis acid catalyst.

    Copyright:

    Attribution Non-Commercial (BY-NC)
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    Halogenation of Benzene

    Reaction type: Electrophilic Aromatic Substitution

    Summary.

    Overall transformation : Ar-H to Ar-X Reagent : normally the halogen (e.g. Br2) with a Lewis acid catalyst The active catalyst is not Fe (0) but the FeX3 formed by reaction of Fe with X2 Electrophilic species : the halonium ion (i.e. X +) formed by the removal of a halide ion by the Lewis acid catalyst Restricted to Cl2 and Br2. I- or F- are usually introduced using alternative methods
    MECHANISM FOR HALOGENATION OF BENZENE Step 1: The bromine reacts with the Lewis acid to form a complex that makes the bromine more electrophilic. Step 2: The electrons of the aromatic C=C act as a nucleophile, attacking the electrophilic Br, and displacing iron tetrabromide. This step destroys the aromaticity giving the cyclohexadienyl cation intermediate.

    Step 3: Removal of the proton from the sp3 C bearing the bromo- group reforms the C=C and the aromatic system, generating HBr and regenerating the active catalyst.

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