7.3 SN1 vs SN2

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    Unreactivity of sp2 Halides

    Aryl and Vinyl halides are unreactive in both SN2 and SN1 reactions.
    Nucleophile is repelled by pi electrons prohibiting SN2.
    The possible carbocation would be highly unstable prohibiting SN1.

    SN1 vs SN2 Chart

    aryl vinyl
    Substrate CH3 > 1° > 2° > 2° (or resonance)
    Nucleophile strong required weak is ok
    Solvent polar aprotic polar protic
    Leaving Group (OTs- > I- > Br- > Cl-)
    or alcohol in acid
    (OTs- > I- > Br- > Cl-)
    or alcohol in acid
    Rearrangements Not Possible Possible
    Stereoselectivity Inversion Racemization

    SN1 vs SN2: Predicting the Product

    Predict the mechanism and substitution product(s) for each of the following:

    SN1 vs SN2 product 1
    SN1 vs SN2 product 2
    SN1 vs SN2 product 3
    SN1 vs SN2 product 4
    SN1 vs SN2 product 5
    SN1 vs SN2 product 6
    SN1 vs SN2 product 7