When 2-(2-(2-bromoethyl)phenyl)acetamide is treated with Br ₂ / NaOH and heated, the major organic product formed is:

Step-by-step solution

The reaction involves two main steps: Hofmann bromamide degradation followed by an intramolecular nucleophilic substitution. First, the primary amide group ( - CH ₂ CONH ₂ ) undergoes Hofmann bromamide degradation in the presence of Br ₂ / NaOH to yield a primary amine with one less carbon. This forms the intermediate 2-(2-(2-bromoethyl)phenyl)methanamine. In the basic medium, the newly formed amine nitrogen acts as a nucleophile and attacks the carbon bearing the bromine atom via an intramolecular S _ N 2 mechanis