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  • Stability of CarbocationsUP2

    Încărcat de

    Scott M Denton
    18 vizualizări2 pagini
    1) The rates of SN1 reactions correspond to the stability of the corresponding carbocations, with more stable carbocations forming at faster rates. 2) Carbocation stability increases with increasing alkyl substituents on the carbocation center, from primary to secondary to tertiary carbocations. 3) Primary carbocations that are resonance stabilized, such as allyl, benzyl, and methoxymethyl carbocations, are more stable than simple primary carbocations but less stable than secondary carbocations. Their reaction rates fall between secondary and tertiary carbocations.

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    Information about the stability of carbocations

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    1) The rates of SN1 reactions correspond to the stability of the corresponding carbocations, with more stable carbocations forming at faster rates. 2) Carbocation stability increases with increasing alkyl substituents on the carbocation center, from primary to secondary to tertiary carbocations. 3) Primary carbocations that are resonance stabilized, such as allyl, benzyl, and methoxymethyl carbocations, are more stable than simple primary carbocations but less stable than secondary carbocations. Their reaction rates fall between secondary and tertiary carbocations.

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    18 vizualizări2 pagini

    Stability of CarbocationsUP2

    Încărcat de

    Scott M Denton
    1) The rates of SN1 reactions correspond to the stability of the corresponding carbocations, with more stable carbocations forming at faster rates. 2) Carbocation stability increases with increasing alkyl substituents on the carbocation center, from primary to secondary to tertiary carbocations. 3) Primary carbocations that are resonance stabilized, such as allyl, benzyl, and methoxymethyl carbocations, are more stable than simple primary carbocations but less stable than secondary carbocations. Their reaction rates fall between secondary and tertiary carbocations.

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    din 2

    Stability of Carbocations (updated)

    Look @ the relative rates of SN1 reactions for various alkyl chlorides:
    Krel

    CH3Cl 1.0

    CH3CH2Cl 1.0

    CH3CHCl 12
    CH3

    H2C CHCH2Cl 40

    CH2Cl 120 These compounds ionize easily


    even though they are primary carbons
    because the carbocation formed by
    CH3O-CH2-Cl >103 ionization is stabilized by
    resonance delocalization
    CH3
    CH3CCl >106
    CH3

    Notice:
    • As the number of R groups on the carbon with the leaving group increases, the
    rate of the SN1 reaction increases.
    • Alkyl halides that form resonance stabilized carbocations have a faster rate of
    reaction.

     The rates of SN1 reactions correspond to the stability of the corresponding


    carbocations!

    From the chart above we can rank the stability of carbocations. Notice that
    primary resonance stabilized carbocations (allyl cation, benzyl cation, and
    methoxymethyl cation) are in between secondary carbocation and tertiary
    carbocations in stability (their rate of SN1 reaction is in between secondary alkyl
    chlorides and tertiary alkyl chlorides.)
    Stability of carbocations:

    H2C CHCH2
    CH3
    CH3C > CH2 > CH3CH > CH3CH2 > > CH3
    CH3 CH3
    CH3O CH2 H2C CH

    3° > resonance- > 2° > 1° > phenyl, > methyl


    tertiary stabilized secondary primary vinyl
    primary (least
    (most
    stable) (allyl, benzyl, stable)
    methoxymethyl)

    Important note:
    Although primary resonance stabilized carbocations (allyl cation, benzyl cation,
    and methoxymethyl cation) are less stable than tertiary carbocations, secondary
    resonance stabilized carbocations more stable than tertiary carbocations.

    Example:

    H2 C CHCHCH3
    CH3
    CHCH3 > CH3C
    CH3
    CH3O CHCH3

    secondary resonance 3°
    stabilized carbocations

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