Electron-withdrawing groups enhance the acidic strength of phenol, with a more pronounced effect at ortho and para positions. Effective delocalization of negative charge in the phenoxide ion occurs when the substituent is at these positions.

Charge delocalization, illustrated by resonance structures I-V, increases the stability of phenoxide ions. The phenol molecule is less stable due to charge separation in its resonance structures, favoring the ionization of phenol.

In alkoxide ions, the negative charge is localized on oxygen, while in phenoxide ions, the charge is delocalized. The delocalization of charge in phenoxide ions contributes to their increased stability compared to the localized charge in alkoxide ions.

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.

The hydroxyl group in phenol is directly attached to the sp² hybridized carbon of the benzene ring, acting as an electron-withdrawing group. This, along with resonance structures, results in a positive charge on the oxygen, making phenols stronger acids than ...

Alkoxide ions are better proton acceptors than hydroxide ions, indicating stronger bases. Alcohols act as Bronsted bases due to the presence of unshared electron pairs on oxygen, making them capable of accepting protons.

Alcohols and phenols react with active metals (e.g., sodium, potassium, aluminum), forming alkoxides/phenoxides and releasing hydrogen. Phenols also react with aqueous sodium hydroxide to produce sodium phenoxides.

The polar nature of the O-H bond contributes to the acidic character of alcohols. Electron-releasing groups like –CH₃ and –C₂H₅ decrease the acid strength by increasing electron density on oxygen.

Alcohols and phenols, despite having comparable molecular masses with hydrocarbons, ethers, haloalkanes, and haloarenes, exhibit higher boiling points due to the presence of intermolecular hydrogen bonding, which is lacking in the other compound classes.

The boiling points of alcohols and phenols increase with an increase in the number of carbon atoms, but in alcohols, boiling points decrease with increased branching due to a decrease in van der Waals forces and surface area.