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  • Substitution Elimination Flowchart

    Enviado por

    Ayah Al-Anani
    145 visualizações2 páginas
    This document outlines the factors that determine whether a nucleophilic substitution (SN) or elimination (E) reaction will occur. It first considers the strength of the nucleophile/base - strong bases favor SN2/E2, while moderate-weak bases allow for any mechanism. It then examines the substrate - primary alkyl halides undergo SN2, tertiary undergo E2/SN1/E1, and secondary can follow multiple paths. Steric effects and reaction conditions like heat can also influence the reaction mechanism.

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    flow chart

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    This document outlines the factors that determine whether a nucleophilic substitution (SN) or elimination (E) reaction will occur. It first considers the strength of the nucleophile/base - strong bases favor SN2/E2, while moderate-weak bases allow for any mechanism. It then examines the substrate - primary alkyl halides undergo SN2, tertiary undergo E2/SN1/E1, and secondary can follow multiple paths. Steric effects and reaction conditions like heat can also influence the reaction mechanism.

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    © All Rights Reserved
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    Sinalizar o conteúdo como inadequado
    145 visualizações2 páginas

    Substitution Elimination Flowchart

    Enviado por

    Ayah Al-Anani
    This document outlines the factors that determine whether a nucleophilic substitution (SN) or elimination (E) reaction will occur. It first considers the strength of the nucleophile/base - strong bases favor SN2/E2, while moderate-weak bases allow for any mechanism. It then examines the substrate - primary alkyl halides undergo SN2, tertiary undergo E2/SN1/E1, and secondary can follow multiple paths. Steric effects and reaction conditions like heat can also influence the reaction mechanism.

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    © All Rights Reserved
    Baixe no formato PDF, TXT ou leia online no Scribd
    Sinalizar o conteúdo como inadequado
    de 2

    First,'look'at'the'

    nucleophile'or'base'

    If'strong'nucleophile'or'base'(nega7vely' If'moderate'to'weak'nucleophile'(typically'uncharged,'or'
    charged,'no'resonance,'not'halide)' charged'but'resonance'stabilized,'or'halide)'

    Look'at'the'substrate'(alkyl'
    SN2'or'E2'(the'nucleophile/base'cannot'wait'for'the'alkyl' halide)'
    halide'to'lose'its'leaving'group'and'become'a'carboca7on)'

    Primary' Ter7ary' Secondary'


    Now,'look'at'the'substrate'(alkyl'
    halide)'
    SN1'or'E1'
    (typically' All'mechanisms'
    SN2' possible'here'
    mixtures'
    Primary' Ter7ary' Secondary'
    ClP,'IP,'CH3CO2P'are' If'alkyl'halide'sterically'
    weak'bases'but' encumbered'at'both''and''
    SN2' E2' SN2'or'E2' reasonable'
    (E2'typically' posi7ons'OR'if'heat'
    nucleophiles'
    major)'

    If'HEAT'or'LARGE,' SN1'more'than'E1'(s7ll' E1'more'than'


    sterically'encumbered' mixture)' SN1'(s7ll'
    BASES' mixture)'

    E2'
    Notes:'
    '
    1. Primary'halides'usually'give'SN2,'occasionally'E2'
    2. Ter=ary'halides'undergo'E2,'or'a'mixture'of'SN1'and'E1'
    3. Sterically'hindered'bases'(potassium'tDbutoxide,'LDA)'give'E2'
    4. Heat'favors'elimina=on'
    5. Secondary'halides'are'more'dicult'to'predict;'you'can'get'a'mixture'of'products'
    6. When'alcohols'are'treated'with'strong'acid'(HX):'only'primary'alcohols'undergo'SN2'
    or'E2.''Secondary'and'ter=ary'alcohols'undergo'SN1'or'E1.'

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