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  • Amines and Nitrogen Compounds-1

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    CBIT CIVIL A1
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    This document discusses the nomenclature of various amines and provides methods for their preparation, including: 1) Reduction of nitro compounds can produce amines by reducing the nitro group to an amine. 2) Reduction of amides and cyanides using lithium aluminum hydride can produce amines. 3) The Gabriel phthalimide synthesis involves reaction of a potassium phthalimide with a halide to form an alkyl phthalimide, which upon hydrolysis produces the amine. Electron withdrawing groups on the aryl group increase the rate of this reaction.

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    AMINES AND NITROGEN COMPOUNDS-1

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    This document discusses the nomenclature of various amines and provides methods for their preparation, including: 1) Reduction of nitro compounds can produce amines by reducing the nitro group to an amine. 2) Reduction of amides and cyanides using lithium aluminum hydride can produce amines. 3) The Gabriel phthalimide synthesis involves reaction of a potassium phthalimide with a halide to form an alkyl phthalimide, which upon hydrolysis produces the amine. Electron withdrawing groups on the aryl group increase the rate of this reaction.

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    © All Rights Reserved
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    32 views8 pages

    Amines and Nitrogen Compounds-1

    Uploaded by

    CBIT CIVIL A1
    This document discusses the nomenclature of various amines and provides methods for their preparation, including: 1) Reduction of nitro compounds can produce amines by reducing the nitro group to an amine. 2) Reduction of amides and cyanides using lithium aluminum hydride can produce amines. 3) The Gabriel phthalimide synthesis involves reaction of a potassium phthalimide with a halide to form an alkyl phthalimide, which upon hydrolysis produces the amine. Electron withdrawing groups on the aryl group increase the rate of this reaction.

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    of 8

    NOMENCLATURE OF 10 20 30 Amines

    MHz Ethanamine

    MHz propanamine

    MHz propan 2 amine

    NH N ethyl Ethanamine

    N N N dimethyl Methanamine

    Me N N
    N
    Me diethyl
    Butan 1 amine
    Me

    Me

    Me N N N diethyl
    me
    Pentan Z amine
    Me
    CHz
    I phenyl Ethanamine
    MHz
    pin
    Me
    Me
    NH N Isopropyl
    Me Me
    2 methyl propanamine

    NHz
    Benzenamine
    or Aniline

    NHz
    Z Amino
    CH Toluene
    Ortho Toluidine

    NHz Benzen 1,2 diamine

    MHz
    10 phenylene diamine

    NHz
    2 Amino
    COOH Benzoic acid
    Anthranilic acid
    Me
    N N dimethyl Beneenamine
    N
    Me or aniline
    Nin dimethyl

    Me
    N N Z Trimethyl Aniline
    N
    Me

    Me

    Me Me N N 2,6 Tetra methyl Aniline


    N
    Me

    Me

    AZIRIDINE IN AZITIDINE
    1

    PYRROLIDINE
    ri pKa 11.33 PIPERIDINE
    I
    N
    H
    pka 11.22
    PYRIDINE
    ni PYRROLE my
    I i

    Quinoline N
    ni ISOQUINOLINE

    QUINDIDINE
    ri
    I
    IMIDAZOLE
    y
    N
    DABCO
    DIAZO BICYCLO OCTANE
    r

    Q Write the structural isomers for Catti.sn


    and each structure must have cyclohexane

    ring
    CH NHz NH CH3 Hz MHz
    MHz
    CHz
    NHL NHL

    CHz
    CHz
    Q Write the structural isomers for Cahan
    and each structure must have Benzene

    ring
    NH CH CH NHL CH3

    NHz
    Hz Hz

    NHz
    NHL
    C5HizN MHz

    NHL NHL MHz

    MHZ
    MHz MHz

    NH NH
    NH
    NH NH

    NH N N

    PREPARATION OF AMINES
    Reduction of Nitro compounds

    R NO LEAHY R NHz

    N 2
    Ha Pd a Pt Ni 42

    nor Fe He
    Aniline

    Coty NIN 645


    AZO RETENE
    Yy NO2zn MHz
    ya Aniline

    v18 É se
    x
    NHOH
    Colts NH NH Colts
    HYDRAZO BENZENE
    phenyl Hydroxyl
    Colts N N Colts
    AZOXY BENZENE

    If two NO
    groups are present on
    benzene at meta position to each
    ring
    other then one NO
    group selectively
    reduced into Nitz in the presence of
    reducing agents like Nau as for Naas
    on any
    reagent which readily produce
    52 base
    MHz
    NOz
    NHU 2S
    or Nass
    No
    NOz

    Reduction of Amides and Cyanides

    R É NH
    Liality
    NABHu
    CH NE

    YEE
    WAI HU R Cha MHz
    R C EN
    LEITH R Nit city
    R m
    N methylamine

    Gabriel Phthalimide Synthesis


    For synthesis of aliphatic for aromatic
    y
    COOH CO Co
    42144

    COOH
    H2O
    of cos
    phthalic Phthalic phthalimid
    Acid
    anhydride
    AIC KOI

    CO
    CO R X
    R Sma cake
    M N potassium
    N
    Alkyl phthalimide
    phthalimide

    Hydrolysis

    COOH
    T R NH
    COOL

    EWG group Halides will increase


    on
    Aryl
    the rate of reaction Unsubstituted Arx
    will not 10 this method
    amine
    by

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