What happens when anisole is nitrated?

Nitration of anisole, which is an aromatic compound with a methoxy group (-OCH3) attached to a benzene ring, leads to the formation of nitroanisole. This reaction typically occurs when anisole is treated with a mixture of concentrated nitric acid and sulfuric acid.

The Nitration Process

During nitration, the electrophilic aromatic substitution mechanism is employed. Here’s a brief overview of the steps involved:

• Formation of the Electrophile: The nitric acid generates the nitronium ion (NO2+), which acts as the electrophile.
• Attack on the Aromatic Ring: The methoxy group is an activating group, directing the electrophile to the ortho and para positions of the benzene ring.
• Formation of Nitroanisole: The nitronium ion substitutes one of the hydrogen atoms on the aromatic ring, resulting in ortho-nitroanisole or para-nitroanisole.

Product Distribution

The methoxy group enhances the reactivity of the ring, leading to a mixture of ortho and para products. However, the para product is usually favored due to less steric hindrance.

Applications of Nitroanisole

Nitroanisoles are important intermediates in organic synthesis and can be further transformed into various chemical compounds, including pharmaceuticals and dyes.

In summary, nitrating anisole results in the formation of nitroanisole, primarily at the ortho and para positions, due to the activating effect of the methoxy group.