The higher electronegativity of sp² hybridized carbon in phenol decreases electron density on oxygen, increasing the polarity of the O-H bond. This leads to greater ionization of phenols compared to alcohols.
What is the impact of the higher electronegativity of sp² hybridized carbon in phenol on the acidity of O-H bond compared to alcohols?
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The higher electronegativity of sp² hybridized carbon in phenol, compared to the sp³ hybridized carbon in alcohols, contributes to the increased acidity of the O-H bond in phenol. In phenol, the oxygen’s lone pair is more effectively delocalized into the aromatic ring due to the greater electronegativity of the sp² carbon. This resonance stabilization enhances the stability of the resulting phenoxide ion, making it easier for phenol to donate a proton. In contrast, the oxygen lone pair in alcohols is less efficiently delocalized, making the O-H bond in alcohols less acidic than that in phenol.