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    Ansh pandey
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    The document discusses diazonium salts, which are organic compounds containing the diazonium functional group (R-N+=N). It provides three key points: 1) Diazonium salts are prepared through diazotization, the conversion of aromatic primary amines to diazonium salts using nitrous acid. This forms stable arenediazonium salts at low temperatures. 2) Diazonium salts are colored solids that are water soluble and stable in the cold but decompose when warmed. Benzenediazonium fluoroborate is water insoluble and stable at room temperature. 3) Diazonium salts undergo characteristic reactions through displacement of the

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    The document discusses diazonium salts, which are organic compounds containing the diazonium functional group (R-N+=N). It provides three key points: 1) Diazonium salts are prepared through diazotization, the conversion of aromatic primary amines to diazonium salts using nitrous acid. This forms stable arenediazonium salts at low temperatures. 2) Diazonium salts are colored solids that are water soluble and stable in the cold but decompose when warmed. Benzenediazonium fluoroborate is water insoluble and stable at room temperature. 3) Diazonium salts undergo characteristic reactions through displacement of the

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    © All Rights Reserved
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    11 views15 pages

    Amines 3

    Uploaded by

    Ansh pandey
    The document discusses diazonium salts, which are organic compounds containing the diazonium functional group (R-N+=N). It provides three key points: 1) Diazonium salts are prepared through diazotization, the conversion of aromatic primary amines to diazonium salts using nitrous acid. This forms stable arenediazonium salts at low temperatures. 2) Diazonium salts are colored solids that are water soluble and stable in the cold but decompose when warmed. Benzenediazonium fluoroborate is water insoluble and stable at room temperature. 3) Diazonium salts undergo characteristic reactions through displacement of the

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    © All Rights Reserved
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    of 15

    AMINES.

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    Flow chart

    Structure Of Amines

    Preparation of Amines
    Classification

    Reduction of Nitro Compounds


    Nomenclature
    Ammonolysis of alkyl halides

    Reduction of nitriles

    Reduction of amides
    Amines
    Physical Property

    -!
    Gabriel phthalimide synthesis

    Hoffmann bromoamide degradation


    reaction

    Chemical reactions

    I
    Basic Character Alkylation/Acylation
    Reaction with
    Arylsulphonyl chloride
    Carbylamine Reaction

    Electrophilic
    Reaction with nitrous acid substitution
    -0*-5-0

    Bhagat
    BBa*
    Godot
    Booger
    .
    -0

    Tq

    -BdoogoEtEoIntonated
    Fish
    3rd

    \
    ←*→ "

    ⇐@i-=---€@EE
    A

    Hatoyama -3
    Tayo

    fi:*
    •
    toady

    a.es?.EieEz
    . .
    -

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    308
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    ¥0688941

    #¥EEsA
    H
    H

    i
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    Diazonium Salts
    diazonium group
    I

    +
    General formula : R N N
    -
    Aryl Group X -
    Br - HSO4- BF -
    ⇐

    Fr
    Cl 4

    + +
    N N N N
    - HSO -
    Cl 4

    (Benzenediazonium Chloride) (Benzenediazonium hydrogensulphate)

    Methods of Preparation :

    Diazotisation :
    The conversion of primary aromatic amines into diazonium salts is known as diazotisation.

    1) Primary aliphatic amines :-


    -
    Cl
    + Primary aliphatic amines form
    R NH 2 + HNO2 R N N
    highly unstable alkyldiazonium salts.
    NaNO2 + HCl

    2) Aromatic Amines :-

    +
    NH2 N N
    -
    HNO2 Cl
    + I

    NaNO2 + HCl (Benzenediazonium Chloride)


    Aromatic Amines
    (Aniline) Salt

    Primary aromatic amines form


    arenediazonium salts which are stable for a short
    time in solution at low temperatures ( 0-5 C ).
    0

    Reason for stability of arenediazonium : Resonance phenomenon

    + + +
    + N N N +
    → N •
    "
    ☒
    N N N N
    Ap
    •
    •

    Ef Fg q⇐ ☒* 9$ Fg

    + +
    Physical Properties :

    +
    N N Colourless crystalline solid
    -
    BE

    Cl
    Tf
    It is readily soluble in water and is stable in cold but reacts
    with water when warmed. It decomposes easily in the dry
    (Benzenediazonium Chloride) state.

    +
    N N
    BF -
    BE Benzenediazonium fluoroborate is water insoluble and stable
    4 at room temperature.

    Chemical Reactions
    Reactions involving displacement of nitrogen

    Gattermann Reaction Sandmeyer reaction


    ×
    ×

    Cl
    - Cu 2 Cl2
    Cl To + N2
    Cl + HCl
    N N
    N2 + Cu/HCl
    #k☒£
    Br
    Cu 2 Br2
    ☒
    *
    + N2
    Br HBr
    Cu/HBr
    N2 + KEE
    CN
    CuCN → . + N2
    KCN
    Other important reactions :

    F
    -
    Heat Cl
    N2 + BF3 + BF -
    +
    Ke
    4
    N N N
    +
    N I
    HBF KI
    EE
    4 Ii + KCl + N2
    NO 2

    NaNO2
    N2 + NaBF4 + *☒
    Cu/Heat
    -
    Cl
    + H
    N N

    H3 PO2
    •¥ + H3 PO3 + HCl + N2
    H2 O

    CH3 CH2 OH
    ☒* + CH3 CHO + HCl + N2

    OH

    H2 O
    ☒* + HCl + N2

    Coupling Reaction :

    OH
    +
    N N N N OH
    - -OH
    Cl
    + D8

    Base

    Phenol p-Hydroxyazobenzne ( Orange Dye )

    NH2
    +
    N N N N NH2
    - +
    Cl H
    + D8
    Acid

    Aniline
    p-Aminoazobenzne ( Yellow Dye )

    The azo products obtained have an extended conjugate system having both the aromatic rings
    joined through the –N=N– bond. These compounds are often coloured and are used as dyes.

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