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' A ' is a neutral organic compound ( M . F : C ₈ H ₉ ON ). On treatment with aqueous Br ₂ / HO ^ (-) , ' A ' forms a compound ' B ' which is soluble in dilute acid. ' B ' on treatment with aqueous NaNO ₂ / HCl (0-5^ C ) produces a compound ' C ' which on treatment with CuCN / NaCN produces ' D '. Hydrolysis of ' D ' produces ' E ' which is also obtainable from the hydrolysis of ' A '. ' E ' on treatment with acidifi

Correct answer

2

Step-by-step solution

Compound A undergoes bromination with aqueous Br₂/HO⁻ to form B, which is soluble in dilute acid, indicating an amino group is present. B undergoes diazotization with NaNO₂/HCl at 0-5°C to form diazonium compound C. The diazonium compound is then treated with CaCN/NaOH to form nitrile compound D. Hydrolysis of D produces carboxylic acid E. When A is treated with acidified KMnO₄, it produces F containing two different types of hydrogen atoms. This reaction sequence is characteristic of anthranilic acid (2-aminobenzo

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