Read the passage carefully and answer the questions :
Replacement of a hydrogen atom in a hydrocarbon by an alkoxy or carboxyl group yields a class of compounds known as ethers. Ethers are classified as symmetrical or unsymmetrical on the basis of groups attached to the oxygen atoms. Diethyl ether, a symmetrical ether, has been widely used as an inhalation anesthetic. Ethers can be prepared by acid catalyzed intermolecular dehydration of alcohols and Williamson's synthesis. Acid catalyzed dehydration of alcohols is not generally preferred as it gives a mixture of elimination and substitution products.
In Williamson's synthesis, an alkyl halide is allowed to react with sodium alkoxide. Ethers containing substituted Alkyl groups may also be prepared by this method. The C-O bond in ether is weakly polar and is cleaved under drastic conditions with excess of hydrogen halides. In electrophilic substitution, the alkoxy group deactivates the aromatic ring and directs the incoming group to ortho and para positions.
Q)The major product in the reaction of anisole with bromine in ethanoic acid, is:
Correct Answer :
o-bromoanisole and p-bromoanisole
Solution :
The correct option is o-bromoanisole and p-bromoanisole.
Anisole (methoxybenzene) contains a methoxy group () attached to the benzene ring. The oxygen atom of the methoxy group has lone pairs of electrons, which can undergo resonance with the pi-electron system of the benzene ring. This resonance effect (+R effect) increases the electron density on the benzene ring, activating it towards electrophilic aromatic substitution reactions.
Due to the resonance structures of anisole, the electron density increases specifically at the ortho and para positions relative to the methoxy group. Therefore, the methoxy group acts as an ortho/para-directing group. When anisole reacts with bromine in the presence of ethanoic acid (acetic acid), bromination occurs at these activated positions.
The reaction yields a mixture of both ortho-bromoanisole and para-bromoanisole as products. Out of these, para-bromoanisole is typically the major product due to less steric hindrance at the para-position compared to the ortho-position, but both isomers are formed. Thus, the reaction of anisole with bromine in ethanoic acid gives o-bromoanisole and p-bromoanisole.
Access expert-curated educational resources and study materials—completely free.
Create, conduct, and manage professional online assessments with Mindyard. Perfect for teachers and institutes.
Copyright © 2026 Mindyard. All Rights Reserved.