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    SN1 VS SN2 VS E1 VS E2

    Uploaded by

    Lily Lilon
    The document summarizes key concepts in organic reaction mechanisms: - SN2, E2, SN1 and E1 reactions are discussed in terms of their rate determining steps, stereochemistry, factors that influence their rates, and preferred substrates. SN2 and E2 occur in one step while SN1 and E1 occur in two steps. - Relative nucleophilicity, basicity, and leaving group ability are compared for different elements based on factors like charge, size, electronegativity and ability to stabilize charge. - Guidelines are provided for determining whether SN2, E2, SN1 or E1 will be the major reaction pathway based on the nucleophile/base, substrate structure and conditions.

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    © All Rights Reserved
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    SN1 VS SN2 VS E1 VS E2

    Uploaded by

    Lily Lilon
    149 views3 pages
    The document summarizes key concepts in organic reaction mechanisms: - SN2, E2, SN1 and E1 reactions are discussed in terms of their rate determining steps, stereochemistry, factors that influence their rates, and preferred substrates. SN2 and E2 occur in one step while SN1 and E1 occur in two steps. - Relative nucleophilicity, basicity, and leaving group ability are compared for different elements based on factors like charge, size, electronegativity and ability to stabilize charge. - Guidelines are provided for determining whether SN2, E2, SN1 or E1 will be the major reaction pathway based on the nucleophile/base, substrate structure and conditions.

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    Chemistry

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    The document summarizes key concepts in organic reaction mechanisms: - SN2, E2, SN1 and E1 reactions are discussed in terms of their rate determining steps, stereochemistry, factors that influence their rates, and preferred substrates. SN2 and E2 occur in one step while SN1 and E1 occur in two steps. - Relative nucleophilicity, basicity, and leaving group ability are compared for different elements based on factors like charge, size, electronegativity and ability to stabilize charge. - Guidelines are provided for determining whether SN2, E2, SN1 or E1 will be the major reaction pathway based on the nucleophile/base, substrate structure and conditions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    149 views3 pages

    SN1 VS SN2 VS E1 VS E2

    Uploaded by

    Lily Lilon
    The document summarizes key concepts in organic reaction mechanisms: - SN2, E2, SN1 and E1 reactions are discussed in terms of their rate determining steps, stereochemistry, factors that influence their rates, and preferred substrates. SN2 and E2 occur in one step while SN1 and E1 occur in two steps. - Relative nucleophilicity, basicity, and leaving group ability are compared for different elements based on factors like charge, size, electronegativity and ability to stabilize charge. - Guidelines are provided for determining whether SN2, E2, SN1 or E1 will be the major reaction pathway based on the nucleophile/base, substrate structure and conditions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 3

    organic chemistry: SN2, E2, SN1, E1

    SN 2

    SN1/E1

    E2

    SN1 and E1 have identical rate determining steps, so they


    generally occur simultaneously and have the same properties.

    mechanism
    big
    obstacle
    stereochemistry
    regiochemistry
    rate
    expression
    Nu quality
    LG quality
    preferred
    solvent?
    substrate

    SN2 and E2
    one stepthis single step is the rate-determining step (RDS)
    SN2: steric hindrance blocking Nu (Nu is in RDS)
    E2: blocking B isnt a big obstacle (B doesnt join substrate)
    SN2: inversion (backside attack, since LG blocks frontside)
    E2: cis vs. trans determined by anti-periplanar transition-state
    E2: possible products from deprotonation of any -carbon
    major product w/ bulky base: less substituted (steric hindrance)
    major product with non-bulky base: more substituted
    Rate = k [substrate] [Nu- or B-], so [Nu-/B-] rate
    (substrate and Nu-/B- are in RDS)
    requires good Nu/strong B (Nu/B is in RDS)
    bulky Nu/B favors E2 vs. SN2 (blocking B isnt a big obstacle)
    requires good leaving group (because leaving group is in RDS)
    polar aprotic (no O-H or N-H bonds)
    (for SN2, hydrogen-bonds to solvent would block Nu)
    (for E2, protic solvent would protonate the base)
    SN2: methyl>1>2; 3 gives no SN2 (substitutents block Nu)
    E2: 1, 2, or 3 (blocking B is not a big obstacle)

    SN1/E1
    two stepsRDS is formation of carbocation
    stabilizing carbocation
    (Nu/B isnt in RDS, so blocking it isnt an obstacle)
    SN1: racemization (planar carbocation intermediate)
    E1: both cis and trans isomers will be produced
    E1: possible products from deprotonation of any -C
    major product: more substituted alkene
    (e--donating alkyl substituents stabilize alkenes)
    Rate = k [substrate], so [Nu-/B-] rate unchanged
    (only the substrate is in RDS)
    can work with a poor Nu/weak B
    (Nu/B isnt in RDS)
    requires good leaving group (because LG is in RDS)
    polar protic (at least one O-H or N-H bond)
    (hydrogen-bonds to solvent stabilize carbocation)
    3 > 2; methyl and 1 give no SN1/E1
    (alkyl substituents stabilize the carbocation)
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    organic chemistry: SN2, E2, SN1, E1

    nucleophilicity
    basicity
    leaving-group ability

    comparing the same element


    charge
    resonance
    negative charge better Nu
    resonance worse Nu
    (charge is stabilized)
    negative charge stronger base
    resonance weaker base
    (charge is stabilized)
    positive charge better LG
    resonance better LG
    (more willing to accept electrons)
    (charge will be stabilized)
    comparing different elements

    big difference
    nucleophilicity
    basicity
    leaving-group ability

    N O F
    P S Cl
    Se Br
    I

    N O F
    P S Cl
    Br
    I
    2

    same row
    electronegativity
    less electronegative better Nu
    (willing to donate electrons)
    less electronegative stronger base
    (willing to donate electrons)
    more electronegative better LG
    (willing to accept electrons)

    same column
    size
    bigger better Nu (usually)
    (big Nus are less hindered by solvent, more polarizable)
    bigger weaker base
    (large base can spread out and stabilize electron density)
    bigger better leaving group
    (big LGs can spread out and stabilize electron density)

    nucleophiles, leaving groups, bases


    nucleophiles
    leaving groups
    N O F
    good Nu (SN2 or SN1) N O F
    N+ O+ good LG
    P- S- Clpoor Nu (SN1 only)
    P S Cl
    P+ S+
    not a LG
    Se Br
    not a Nu
    Br
    II
    The carbon is attached to
    the oxygen, not to the sulfur.
    cyanide NC (charge on the C)
    azide N3
    bases
    Nucleophiles and bases shown with charges before attacking.
    Leaving groups shown with charges before leaving.
    N- Ostrong base (E2)
    The tables for individual atoms assume no resonance. Resonance
    P S Cl
    weak base (E1)
    makes atoms into worse nucleophiles and bases and into better leaving
    Brnot a base
    groups.
    I
    www.freelance-teacher.com

    organic chemistry: SN2, E2, SN1, E1

    what happens in SN2, SN1, E2, and E1 mechanisms


    what happens
    One step: Nucleophile joins carbon and leaving group leaves carbon
    Step one: Leaving group leaves carbon
    Step two: Nucleophile joins carbon
    One step: Base takes hydrogen, bond forms between and carbons, leaving group leaves carbon.
    Step one: Leaving group leaves carbon
    Step two: Base takes hydrogen, bond forms between and carbons

    SN 2
    SN 1
    E2
    E1

    big obstacle
    steric hindrance
    stabilizing the
    carbocation
    none
    stabilizing the
    carbocation

    how to determine SN2 vs. E2 vs. SN1 vs. E1 for haloalkane and alkylsulfonate substrates
    poor Nu / weak base
    good Nu / weak base
    good Nu / strong base
    - O with no formal charge
    Cl , Br , I , NC , N3 , S , Se , or
    N- , OCH3COO
    or N, S, or Se with no formal charge
    methyl -carbon no reaction
    SN 2 1
    E2 with tert-butyl-oxide (bulky base) 2
    1 -carbon
    Otherwise, SN2
    2 -carbon 95% SN1
    SN 2 1
    E2
    5% E1 (usually not shown)
    3 -carbon 95% SN1
    95% SN1
    E2
    5% E1 (usually not shown) 5% E1 (usually not shown)
    For cases with 95% SN1, 5% E1, E1 products are generally not shown unless the problem specifies all possible products.
    1
    2

    No reaction if beta-carbon is 4.
    SN2 for methyl -carbon.

    The table displays the major reaction(s) for each casein some cases there may be significant levels of other competing
    reactions.
    This table may not give the correct answer in all real-world situations, but it will generally be accurate for the questions that
    are typical of exams.

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