Question

What is the major product Y in the following reaction sequence?

• A.
• B.
• C.
• D.

Hint:

Diazotization followed by nucleophilic substitution and electrophilic aromatic substitution are classic transformations in aromatic chemistry.

Answer 1

The Correct Option is C

The sequence first involves diazotization of aniline to form a diazonium salt. 
Hydrolysis gives phenol, which undergoes Williamson ether synthesis to give anisole. 
Bromination of anisole in acetic acid selectively yields para-bromoanisole as the major product.