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    Deprotonation: Proton Brønsted-Lowryacid Acid-Basereaction Conjugatebase Brønsted-Lowrybase Protonation Conjugateacid

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    Deprotonation is the removal of a proton (H+) from an acid during an acid-base reaction. This forms the conjugate base of the acid. The ability of a molecule to lose a proton, known as its pKa value, depends on how stable the conjugate base is. A more stable conjugate base indicates a stronger acid that more easily donates its proton. Common bases used for deprotonation include hydroxides for weaker acids and hydrides for stronger acids. Deprotonation increases a molecule's nucleophilicity by making it more electron-rich, which can impact chemical reactivity.

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    Deprotonation: Proton Brønsted-Lowryacid Acid-Basereaction Conjugatebase Brønsted-Lowrybase Protonation Conjugateacid

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    Tanzim
    31 views3 pages
    Deprotonation is the removal of a proton (H+) from an acid during an acid-base reaction. This forms the conjugate base of the acid. The ability of a molecule to lose a proton, known as its pKa value, depends on how stable the conjugate base is. A more stable conjugate base indicates a stronger acid that more easily donates its proton. Common bases used for deprotonation include hydroxides for weaker acids and hydrides for stronger acids. Deprotonation increases a molecule's nucleophilicity by making it more electron-rich, which can impact chemical reactivity.

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    Deprotonation

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    Deprotonation is the removal of a proton (H+) from an acid during an acid-base reaction. This forms the conjugate base of the acid. The ability of a molecule to lose a proton, known as its pKa value, depends on how stable the conjugate base is. A more stable conjugate base indicates a stronger acid that more easily donates its proton. Common bases used for deprotonation include hydroxides for weaker acids and hydrides for stronger acids. Deprotonation increases a molecule's nucleophilicity by making it more electron-rich, which can impact chemical reactivity.

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    31 views3 pages

    Deprotonation: Proton Brønsted-Lowryacid Acid-Basereaction Conjugatebase Brønsted-Lowrybase Protonation Conjugateacid

    Uploaded by

    Tanzim
    Deprotonation is the removal of a proton (H+) from an acid during an acid-base reaction. This forms the conjugate base of the acid. The ability of a molecule to lose a proton, known as its pKa value, depends on how stable the conjugate base is. A more stable conjugate base indicates a stronger acid that more easily donates its proton. Common bases used for deprotonation include hydroxides for weaker acids and hydrides for stronger acids. Deprotonation increases a molecule's nucleophilicity by making it more electron-rich, which can impact chemical reactivity.

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    Deprotonation

    Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen
    cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.[1][2] The species formed is
    the conjugate base of that acid. The complementary process, when a proton is added
    (transferred) to a Brønsted–Lowry base, is protonation (or hydronation). The species formed is
    the conjugate acid of that base.

    Deprotonation of acetic acid by a hydroxide ion

    A species that can either accept or donate a proton is referred to as amphiprotic. An example is
    the H2O (water) molecule, which can gain a proton to form the hydronium ion, H3O+, or lose a
    proton, leaving the hydroxide ion, OH−.

    The relative ability of a molecule to give up a proton is measured by its pKa value. A low pKa
    value indicates that the compound is acidic and will easily give up its proton to a base. The pKa
    of a compound is determined by many aspects, but the most significant is the stability of the
    conjugate base. This is primarily determined by the ability (or inability) of the conjugated base to
    stabilize negative charge. One of the most important ways of assessing a conjugate base's
    ability to distribute negative charge is using resonance. Electron withdrawing groups (which can
    stabilize the molecule by increasing charge distribution) or electron donating groups (which
    destabilize by decreasing charge distribution) present on a molecule also determine its pKa.
    The solvent used can also assist in the stabilization of the negative charge on a conjugated
    base.

    Bases used to deprotonate depend on the pKa of the compound. When the compound is not
    particularly acidic, and, as such, the molecule does not give up its proton easily, a base stronger
    than the commonly known hydroxides is required. Hydrides are one of the many types of
    powerful deprotonating agents. Common hydrides used are sodium hydride and potassium
    hydride. The hydride forms hydrogen gas with the liberated proton from the other molecule. The
    hydrogen is dangerous and could ignite with the oxygen in the air, so the chemical procedure
    should be done in an inert atmosphere (e.g., nitrogen).

    Deprotonation can be an important step in a chemical reaction. Acid–base reactions typically


    occur faster than any other step which may determine the product of a reaction. The conjugate
    base is more electron-rich than the molecule which can alter the reactivity of the molecule. For
    example, deprotonation of an alcohol forms the negatively charged alkoxide, which is a much
    stronger nucleophile.

    To determine whether or not a given base will be sufficient to deprotonate a specific acid,
    compare the conjugate base with the original base. A conjugate base is formed when the acid is
    deprotonated by the base. In the image above, hydroxide acts as a base to deprotonate the
    carboxylic acid. The conjugate base is the carboxylate salt. In this case, hydroxide is a strong
    enough base to deprotonate the carboxylic acid because the conjugate base is more stable
    than the base because the negative charge is delocalized over two electronegative atoms
    compared to one. Using pKa values, the carboxylic acid is approximately 4 and the conjugate
    acid, water, is 15.7. Because acids with higher pKa values are less likely to donate their protons,
    the equilibrium will favor their formation. Therefore, the side of the equation with water will be
    formed preferentially. If, for example, water, instead of hydroxide, was used to deprotonate the
    carboxylic acid, the equilibrium would not favor the formation of the carboxylate salt. This is
    because the conjugate acid, hydronium, has a pKa of -1.74, which is lower than the carboxylic
    acid. In this case, equilibrium would favor the carboxylic acid.

    References

    1. Zumdahl, S. S. (1986). Chemistry. Lexington, MA: Heath. ISBN 0-669-04529-2.

    2. Henry Jakubowski, Biochemistry Online Chapter 2A3,


    https://employees.csbsju.edu/hjakubowski/classes/ch331/protstructure/PS_2A3_AA_Charges.html
    , accessed 12/2/2020
    Retrieved from
    "https://en.wikipedia.org/w/index.php?
    title=Deprotonation&oldid=1055400619"


    Last edited 1 month ago by Ohnoitsjamie

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