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JEE Main Chemistry Amines 2026 JEE Main 2026 (22 January Shift 1)

JEE Main Chemistry Question (2026) — Solution

Question

' 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 acidified KMnO _ 4 produces ' F '. ' F ' contains two different types of hydrogen atoms. The structure of ' A ' is

Options

  1. A.
  2. B.
  3. C.
  4. D.

Answer

C.

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-aminobenzoic acid), where the amino group directs bromination to the para position, and subsequent reactions proceed through the diazonium intermediate. The structure shown in option (3), which is 2-aminobenzoic acid, fits all these transformations.

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