Identify the major product of the following reaction sequence: (i) Br ₂, NaOH (ii) MeOH / H ⁺ (iii) NaOMe

Step-by-step solution

The given starting material is 3-(2-acetylphenyl)propanoic acid. Step (i): The reagent Br ₂ and NaOH is used for the haloform reaction. The methyl ketone group ( - COCH ₃ ) is oxidized to a carboxylate salt, while the propanoic acid group is also converted to its sodium salt. Upon acidic workup (implied for the next step), the product is a dicarboxylic acid, 2-(2-carboxyethyl)benzoic acid. Step (ii): Treatment with MeOH and H ⁺ leads to Fischer esterification of both carboxylic acid groups. This yields a diester, m