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    Understanding The Elimination Reaction

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    nirmla
    The document describes the reaction mechanisms of elimination reactions. Cyclopropyl methyl substrates undergo solvolysis with abnormally high rates, producing rearranged cyclopropyl-methyl and cyclobutyl compounds. The reaction of tert-butyl bromide with dilute sodium hydroxide proceeds through an E1 mechanism, forming a carbocation intermediate. With concentrated sodium hydroxide, an alkene product is formed via an elimination reaction instead of substitution. Dehydrohalogenation and alcohol dehydration reactions proceed through a two-step E1 mechanism, with the rate-determining step being unimolecular formation of the carbocation intermediate.

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    Understanding The Elimination Reaction

    Uploaded by

    nirmla
    20 views33 pages
    The document describes the reaction mechanisms of elimination reactions. Cyclopropyl methyl substrates undergo solvolysis with abnormally high rates, producing rearranged cyclopropyl-methyl and cyclobutyl compounds. The reaction of tert-butyl bromide with dilute sodium hydroxide proceeds through an E1 mechanism, forming a carbocation intermediate. With concentrated sodium hydroxide, an alkene product is formed via an elimination reaction instead of substitution. Dehydrohalogenation and alcohol dehydration reactions proceed through a two-step E1 mechanism, with the rate-determining step being unimolecular formation of the carbocation intermediate.

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    Understanding the Elimination reaction

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    The document describes the reaction mechanisms of elimination reactions. Cyclopropyl methyl substrates undergo solvolysis with abnormally high rates, producing rearranged cyclopropyl-methyl and cyclobutyl compounds. The reaction of tert-butyl bromide with dilute sodium hydroxide proceeds through an E1 mechanism, forming a carbocation intermediate. With concentrated sodium hydroxide, an alkene product is formed via an elimination reaction instead of substitution. Dehydrohalogenation and alcohol dehydration reactions proceed through a two-step E1 mechanism, with the rate-determining step being unimolecular formation of the carbocation intermediate.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    20 views33 pages

    Understanding The Elimination Reaction

    Uploaded by

    nirmla
    The document describes the reaction mechanisms of elimination reactions. Cyclopropyl methyl substrates undergo solvolysis with abnormally high rates, producing rearranged cyclopropyl-methyl and cyclobutyl compounds. The reaction of tert-butyl bromide with dilute sodium hydroxide proceeds through an E1 mechanism, forming a carbocation intermediate. With concentrated sodium hydroxide, an alkene product is formed via an elimination reaction instead of substitution. Dehydrohalogenation and alcohol dehydration reactions proceed through a two-step E1 mechanism, with the rate-determining step being unimolecular formation of the carbocation intermediate.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
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    Neighbouring group
    participation by
    Cyclopropyl methyl substrates
    solvolyse with abnormally high rates.
    Species having
    lone pair
    The products often include not
    Aromatic rings as only disarranged cyclopropyl-
    neighbouring groups methyl, but also cyclobutyl
    and homoallylic compounds.

    Cyclopropyl methyl system


    EtOH H2O
    +
    ~ 48%

    ~ 47% ~ 5%
    NaOH,
    H2O
    AcOH
    AcOH
    SOCl2
    Ether
    A PCl5

    B C6H5-CH2-SNa
    Δ
    C SOCl2

    D HI
    Δ
    A B

    C D
    A C

    B D
    Reaction of t-BuBr
    slow
    with dil. NaOH

    t-Butyl
    bromide fast or

    t-butanol
    Reaction of t-BuBr
    with conc. NaOH

    + + +

    t-Butyl Isobutene
    bromide (2-Methylpropene)
    The reaction stops being a substitution
    and an alkene is formed instead.

    Overall, HBr is lost from


    the alkyl halide, and the reaction
    is known as an elimination.
    It is an organic reaction in which two groups/substituents/atoms
    are removed from a molecule so that a new bond is formed.

    General reaction

    When two atoms/substituents


    are removed from the adjacent
    atoms (𝝰 and 𝛃 positions) to
    form a new multiple bond.
    𝛃

    Alkene

    Also known as 1,2-elimination


    𝛃

    E1

    E2
    𝛃-Elimination
    reactions
    E1cB

    Ei
    E1 describes an elimination reaction
    ELIMINATION (E) in which RDS is unimolecular (1).

    UNIMOLECULAR The rate-determining step (RDS)


    refers to the ionisation of the substrate
    to give a carbocation and it
    does not involve the base.
    Rate = k[Alkyl halide]

    RDS

    Carbocation
    Step 1 Formation of carbocation

    Slow
    X + X‒

    Carbocation
    Step 2 Attack of base

    + +
    TS (1)

    TS (2)
    Free energy (∆G)

    Bˉ Xˉ
    Bˉ

    Progress of the reaction


    Examples
    It is a unimolecular,
    1
    two-step process.
    Dehydrohalogenation
    of alkyl halide

    The reaction intermediate


    2 is a carbocation. Hence,
    Dehydration of alcohol
    rearrangement is possible.
    Step 1 Formation of carbocation
    Mechanism of
    Dehydrohalogenation
    Step 2 Attack of base
    Step 1 Formation of carbocation

    Slow
    I + I‒

    Carbocation
    Step 2 Attack of base

    + +
    CH3OH
    Δ
    CH3OH
    (X)
    Δ

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