Structures, Reactions, Uses and Properties of Monosubstituted Benzene Compounds

Structures, Reactions, Uses and Properties of Monosubstituted Benzene Compounds

Monosubstituted Benzene Compounds


  • Monosubstituted benzene is a type of aromatic compound in which a single hydrogen atom in the benzene ring is replaced by a substitute (R), denoted as C6H5-R.
  • Examples include Phenol (C6H5-OH), Aniline (C6H5-NH2), and Toluene (C6H5-CH3).


  • Monosubstituted benzene compounds primarily undergo three types of reactions: Electrophilic aromatic substitution, Nucleophilic aromatic substitution, and Oxidative reactions.
  • For example, Toluene reacts with a mixture of nitric and sulfuric acid to yield nitrotoluene in an electrophilic substitution reaction.
  • Aniline can be acylated with acyl chlorides or anhydrides to form secondary amides.
  • Phenol can be oxidised to form benzoquinone, a type of organic compound widely used in industry.


  • Toluene is widely used as a solvent, in the production of benzene and xylene, and in the manufacture of drugs and dyes.
  • Aniline is used in the manufacture of polyurethane foam, rubber, dyes, drugs, plastics, and photographic chemicals.
  • Phenol is used in the production of plastics, resins, disinfectants, pharmaceuticals, and dyes.


  • Monosubstituted benzene compounds generally have higher boiling points and are less volatile than the parent benzene due to the ability of the substitute to form dipole-dipole interactions or hydrogen bonds.
  • Compared to benzene, the addition of a substitute can increase the chemical reactivity of the benzene ring, as seen in reactions involving nucleophile or electrophile.
  • The presence of a substitute also affects the acidic or basic properties of benzene. For example, aniline is a weak base while phenol is a weak acid.

Achieving an understanding of structures, reactions, uses, and properties of monosubstituted benzene compounds is a key step in mastering Applications of Organic Chemistry.