One of the first methods that was used for determining the relative orientations of substituents on aromatic rings was devised by Korner. The “Korner Method of Absolute Orientation” was first applied to determine the structuresof the three isomeric dibromobenzenes A, B, and C. Each isomer can be converted into one or more mononitro derivatives. Isomer A produces one mononitro derivative when treated with nitric acid, isomer B yields two mononitro derivatives and isomer C produces three mononitro derivatives. All mononitro derivatives have the same molecular formula C6H3Br2NO2. Based on this information, assign structural formulas to A, B, and C. There are three positional isomers of dibromobenzene: o, m, and p. These are A, B, and C but which is which?
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The solution determines the relative orientations of substituents on aromatic rings was devised by Korner.