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Guilherme Mazui

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What is the Difference Between Alkoxide and Phenoxide?

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The main difference between an alkoxide and a phenoxide lies in the substituent attached to the oxygen atom. Both alkoxides and phenoxides are anions, but they have distinct properties and are important functional groups in chemical synthesis reactions.

Alkoxides:

  • Conjugate base of an alcohol, with the general chemical formula RO−, where R is the organic substituent.
  • Strong bases and good nucleophiles when R is not bulky.
  • Occur widely as intermediates in various reactions and are used as catalysts and in coatings.

Phenoxides:

  • Conjugate base of phenol, with the general chemical formula C6H5O−.
  • Less basic and less nucleophilic than alkoxides due to the resonance stabilization of the phenoxide anion.
  • Phenol is more acidic than a typical alcohol, making phenoxides weaker bases than alkoxides.

In summary, both alkoxides and phenoxides are anions and play crucial roles in chemical synthesis reactions. While alkoxides are derived from alcohols and are generally strong bases, phenoxides are derived from phenols and are less basic due to resonance stabilization.

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  • What is the Difference Between Alkoxide and Phenoxide?
  • Comparative Table: Alkoxide vs Phenoxide

    • Comparative Table: Alkoxide vs Phenoxide

    Here is a table comparing the differences between alkoxides and phenoxides:

    Property Alkoxides Phenoxides
    Formation Alkoxides form when the hydrogen atom is removed from the -OH group of an alcohol. Phenoxides form when the hydrogen atom is removed from the -OH group of a phenol molecule.
    Chemical Formula General chemical formula: RO-. General chemical formula: C6H5O-.
    Acidity Alkoxides are generally less acidic than phenoxides. Phenoxides are more acidic than alkoxides due to resonance stabilization.
    Basicity Alkoxides can act as strong bases and are often used as reagents in organic chemistry. Phenoxides can also act as bases, but they are less basic than alkoxides.
    Nucleophilicity Alkoxides can act as good nucleophiles when the R group is a simple alkyl group (not a bulky group). Phenoxides are less nucleophilic than alkoxides due to the delocalization of the negative charge over the aromatic ring.
    Stability Alkoxides are stabilized by the solvation effect, which can be reduced by steric effects in bulky alkoxides. Phenoxides are stabilized by resonance stabilization, which allows the negative charge to be delocalized over the aromatic ring.

    Both alkoxides and phenoxides are anions and play important roles as functional groups in chemical synthesis reactions.

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    Guilherme Mazui

    Guilherme Mazui is graduated in journalism from the Federal University of Minas Gerais (UFMG) and a master's degree in Communication from the University of São Paulo (USP). In addition, he has experience in advertising writing and has worked as a content editor in several companies.