Bromination of 4-nitrotoluene is directed by the methyl group to the position ortho to it, which is also meta to the nitro group, giving 2-bromo-4-nitrotoluene as the first product. Tin and hydrochloric acid reduce the nitro group to an amino group, which is diazotised at low temperature, and hypophosphorous acid then replaces the diazonium group by hydrogen to leave 2-bromotoluene. Alkaline potassium permanganate followed by acidification oxidises the methyl group to a carboxylic acid. The first isolated product is 2-bromo-4-nitrotoluene and the final product is 2-bromobenzoic acid.
JEE Main · 2023 · 25 Jan 2023 · Shift 1 · Single correct option
