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    NOTES-The Acidity of Terminal Alkynes PDF

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    Shashikant Thakre
    The terminal hydrogen of a terminal alkyne is more acidic than other C-H bonds due to the stability of its deprotonated form, an acetylide anion. Upon deprotonation, the terminal alkyne forms a carbon-centered acetylide anion that is sp hybridized, which is better at stabilizing negative charge than sp2 or sp3 hybridized carbons. This makes the pKa of a terminal alkyne hydrogen around 25, lower than the pKa of 44 for a vinylic hydrogen.

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    NOTES-The Acidity of Terminal Alkynes PDF

    Uploaded by

    Shashikant Thakre
    262 views1 page
    The terminal hydrogen of a terminal alkyne is more acidic than other C-H bonds due to the stability of its deprotonated form, an acetylide anion. Upon deprotonation, the terminal alkyne forms a carbon-centered acetylide anion that is sp hybridized, which is better at stabilizing negative charge than sp2 or sp3 hybridized carbons. This makes the pKa of a terminal alkyne hydrogen around 25, lower than the pKa of 44 for a vinylic hydrogen.

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    NOTES-The_Acidity_of_Terminal_Alkynes.pdf

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    The terminal hydrogen of a terminal alkyne is more acidic than other C-H bonds due to the stability of its deprotonated form, an acetylide anion. Upon deprotonation, the terminal alkyne forms a carbon-centered acetylide anion that is sp hybridized, which is better at stabilizing negative charge than sp2 or sp3 hybridized carbons. This makes the pKa of a terminal alkyne hydrogen around 25, lower than the pKa of 44 for a vinylic hydrogen.

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    NOTES-The Acidity of Terminal Alkynes PDF

    Uploaded by

    Shashikant Thakre
    The terminal hydrogen of a terminal alkyne is more acidic than other C-H bonds due to the stability of its deprotonated form, an acetylide anion. Upon deprotonation, the terminal alkyne forms a carbon-centered acetylide anion that is sp hybridized, which is better at stabilizing negative charge than sp2 or sp3 hybridized carbons. This makes the pKa of a terminal alkyne hydrogen around 25, lower than the pKa of 44 for a vinylic hydrogen.

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    The Alkyne’s Terminal Hydrogen Is Acidic

    CH3 C C CH3 CH3 C C H


    the triple bond ends
    an internal alkyne a terminal alkyne in a hydrogen atom

    Compared to other C-H bonds,


    the terminal hydrogen of a
    terminal alkyne is acidic. Yes, compared to other C–H
    bonds this one is acidic
    it is a weak acid, but
    comparatively speaking, it is
    acidic. Deprotonation results
    in a carbon-centered anion that
    CH3 C C H H + CH3 C C
    an acetylide anion
    is sp hybridized. This anion is
    called an acetylide anion. As pKa = 25
    stated earlier, sp hybrid orbitals
    are more effective at
    stabilizing negative charge
    than sp2 or sp3 orbitals. It is H
    H
    the stability of the anion that CH2 C H +
    makes the C-H of a terminal
    CH2
    alkyne more acidic than other
    H
    a vinylic anion
    C-H bonds.
    pKa = 44

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