Structures, Reactions, Uses and Properties of Monosubstituted Benzene Compounds

Monosubstituted Benzene Compounds

Structures

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).

Reactions

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.

Uses

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.

Properties

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.