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  • Haloalkanes

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    GAMEPORIUM
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    The document summarizes several substitution reactions including Sn1, Sn2, Grignard's reaction, E1, and E2. It provides information on the mechanism, starting materials, solvents/catalysts, and products for each reaction. For example, it states that Sn1 is a unimolecular, two step reaction with a carbocation intermediate that favors tertiary substrates. It also notes that the leaving group ability is OH < Cl < Br < I ~ H2O under acidic conditions.

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    Original Title

    Haloalkanes (1)

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    The document summarizes several substitution reactions including Sn1, Sn2, Grignard's reaction, E1, and E2. It provides information on the mechanism, starting materials, solvents/catalysts, and products for each reaction. For example, it states that Sn1 is a unimolecular, two step reaction with a carbocation intermediate that favors tertiary substrates. It also notes that the leaving group ability is OH < Cl < Br < I ~ H2O under acidic conditions.

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    © All Rights Reserved
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    3 views2 pages

    Haloalkanes

    Uploaded by

    GAMEPORIUM
    The document summarizes several substitution reactions including Sn1, Sn2, Grignard's reaction, E1, and E2. It provides information on the mechanism, starting materials, solvents/catalysts, and products for each reaction. For example, it states that Sn1 is a unimolecular, two step reaction with a carbocation intermediate that favors tertiary substrates. It also notes that the leaving group ability is OH < Cl < Br < I ~ H2O under acidic conditions.

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    of 2

    Mechanism Name Starting Material Solvent/Catalyst Product

    Tertiary
    Sn1 Tertiary OH HX in ether
    Synthesize RX Haloalkane
    with -OH Primary/Secondary PBr2 in ether Primary/Secondary
    Sn2
    OH SOCl2 in pyridine Haloalkane
    RX
    Where,
    Grignard’s reagent R – 1-3* alkyl, vinyl, Mg in ether or THF R-Mg-X
    aryl
    X- Cl, Br, I
    Neutral/acidic
    conditions using
    hydroxyl solvent or
    Sn1 water

    Unimolecular, 2 Reactivity of leaving


    Tertiary (forms
    step, w/ grp:
    most stable
    carbocation RNu
    carbocation
    intermediate OH<Cl<Br<I ~ H2O
    intermediates)
    Under acidic, -OH
    Dependent: RX becomes better
    (substrate) leaving grp in the
    form of its
    conjugate acid
    (water)
    Sn2

    Bimolecular, 1
    step, methyl &
    1-2* carbons, no Reactivity of leaving
    carbocation grp:
    Primary and
    intermediate, RNu
    Secondary
    stereochemistry OH, NH2, OR< F<
    occurs, 180 Cl<Br<I
    degrees angle

    Dependent: Nü
    & RX (substrate)
    En2 Bimolecular
    Tertiary OH
    reaction Alkene product
    Primary OH and strong stable
    (carbocation Ethanolic hydroxide HX biproduct
    En1 Unimolecular intermediate) (-OH in ethanol)
    reaction (based on Zaitsev’s
    If E1cB, carbanion rule)
    intermediate

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