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when benzyl chloride is boiled with aque...

when benzyl chloride is boiled with aqueous `KOH` solution and the solution is acidified by a few drops of dilute `HNO_(3)` followed by `AgNO_(3)` solution, a white precipitate is formed. However, no such precipitate is noticed when the reaction is carried with chlorobenzene. explain.

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In case of `C_(6)H_(5)CH_(2)Cl`, the benzyl carbocation `(C_(6)H_(5) overset(o+)(C)H_(2))` formed by releasing `Cl^(-)` ion is resonance stabilised. Therefore, the `C - Cl` bond can cleave to form `KCl`. However, the phenyl carbocation `(C_(6)overset(o+)(H)_(5))` expected to be formed in case of chlorobenzene does not show any resonance. therefore, `C - Cl` bond does not cleave in case of chlorobenzene and no white precipitate is formed in this case.
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Knowledge Check

  • When aqueous solution of potassium fluoride is added to the blue coloured aqueous CuSO_(4) solution , a green precipitate is formed . This observation can be explained as follows .

    A
    On adding `KF , H_(2)O` being weak field ligand is replaced by `F^(-)` ions forming `[CuF_(4)]^(2-)` which is green in colour .
    B
    Potassium is coordinated to `[Cu(H_(2)O)_(4)]^(2+)` ion present in `CuSO_(4)` and gives green colour .
    C
    On adding `KF , Cu^(2+)` are replaced by `K^(+)` forming a green complex .
    D
    Blue colour of `CuSO_(4)` and yellow colour of KF form green colour on mixing .

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