Phenols vs Alcohols: Why Phenols are More Acidic?
Introduction
Phenols and alcohols are both organic compounds containing hydroxyl (-OH) group. However, phenols are more acidic in nature than alcohols. This can be attributed to several factors which are discussed below.
Electronic Effects
The acidity of a compound is determined by the ease with which it can donate a proton (H+). In phenols, the hydroxyl group is attached to an aromatic ring which has a delocalized π-electron system. This system creates an electron-withdrawing effect, making the hydroxyl group more acidic than in alcohols. In contrast, alcohols do not possess this electron-withdrawing effect as the hydroxyl group is attached to a non-aromatic carbon chain.
Resonance Stabilization
Phenols also exhibit resonance stabilization due to the presence of the aromatic ring. The delocalized π-electron system in the ring allows for the formation of resonance structures where the negative charge of the deprotonated hydroxyl group is spread over the entire ring. This results in the stabilization of the negative charge and increases the acidity of the compound.
Steric Effects
In alcohols, the -OH group is attached to a sp3 hybridized carbon atom which can undergo steric hindrance due to the size of the substituents attached to it. This results in a decrease in the acidity of the compound as the proton becomes more difficult to remove. In contrast, phenols possess an sp2 hybridized carbon atom which does not undergo steric hindrance due to the presence of the aromatic ring.
Conclusion
In summary, the acidity of phenols is higher than that of alcohols due to the presence of an electron-withdrawing effect, resonance stabilization, and no steric hindrance. This makes phenols useful in various chemical reactions and applications such as as a starting material for the synthesis of pharmaceuticals and dyes.