Reactions of Aromatic Compounds Using Methylbenzene or Methoxybenzene

Reactions of Aromatic Compounds

Aromatic compounds such as methylbenzene or methoxybenzene are compounds that contain a benzene ring, a cyclic structure with six carbon atoms and alternating single and double bonds. The unique stability of these compounds drives many of their characteristic reactions.

Electrophilic Substitution Reactions

Electrophilic substitution is the most common reaction of aromatic compounds. This is because of the presence of delocalised π electrons in the benzene ring which can draw in and react with electrophiles.
Methylbenzene can undergo nitration, sulphonation, and halogenation through the aid of a halogen carrier.
In the nitration of methylbenzene, a nitro group replaces a hydrogen atom on the benzene ring. This is facilitated by the electrophile, the nitronium ion (NO_2^+), formed from the reaction of concentrated nitric and sulphuric acid.
In halogenation, a halogen atom substitutes a hydrogen atom. This reaction requires a halogen carrier, such as FeBr3 for bromination or AlCl3 for chlorination.
Despite having a methoxy group, methoxybenzene undergoes similar electrophilic substitution reactions to methylbenzene.

Nucleophilic Substitution Reactions

Nucleophilic substitution in aromatic compounds is less common because the benzene ring is less likely to react with nucleophiles.
However, methoxybenzene can participate in nucleophilic substitution reactions due to the activating effect of the oxygen atom in the methoxy group.
Under acidic conditions, the reaction of methoxybenzene with a nucleophile leads to the substitution of the methoxy group.

Oxidation Reactions

Methylbenzene can be oxidised to benzoic acid particularly when using a strong oxidising agent such as potassium manganate(VII) solution (KMnO4) under reflux. However, this reaction requires harsh conditions as the methyl group is quite stable.
Unlike methylbenzene, methoxybenzene doesn’t undergo oxidation as the methoxy group is resistant to it.

Understanding the reactions of aromatic compounds like methylbenzene and methoxybenzene is crucial in mastering the foundations of organic chemistry. This provides the basis for understanding the reactivity, stability and synthetic utility of these compounds.