Phenol is commercially produced synthetically nowadays, but it was first isolated from coal tar in the early nineteenth century.

Commercially, carboxylic acids are reduced to alcohols by first converting them to esters, followed by catalytic hydrogenation. Lithium aluminium hydride (LiAlH₄) is considered less economical for this purpose due to its high cost, and it is primarily used for specialized ...

Aldehydes yield primary alcohols, while ketones give secondary alcohols upon reduction. Reduction by lithium aluminium hydride involves the addition of hydride ions and is an effective method for obtaining alcohols from aldehydes and ketones.

Aldehydes and ketones are reduced to alcohols by catalytic hydrogenation, employing finely divided metals like platinum, palladium, or nickel as catalysts. Alternatively, sodium borohydride (NaBH₄) or lithium aluminium hydride (LiAlH₄) can be used.

In hydroboration–oxidation, borane adds to the double bond with the boron atom attaching to the sp² carbon carrying more hydrogen atoms, contrary to Markovnikov’s rule. The reaction yields excellent alcohol formation.

Hydroboration–oxidation involves the reaction of alkenes with diborane to form trialkyl boranes, which are then oxidized to alcohols by hydrogen peroxide in the presence of aqueous sodium hydroxide. This process contradicts Markovnikov’s rule as the boron atom attaches to the ...

Reactions with carboxylic acids and acid anhydrides require concentrated sulfuric acid, while reactions with acid chlorides use a base like pyridine. Acetylation, as seen in the production of aspirin from salicylic acid, involves introducing an acetyl group (CH₃CO) into alcohols ...

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.