' A' is a neutral organic compound (M. F : 
). On treatment with aqueous 
, ' A ' forms a compound ' B ' which is soluble in dilute acid. ' B ' on treatment with aqueous 
produces a compound ' C ' which on treatment with 
produces ' D '. Hydrolysis of ' D ' produces ' E ' which is also obtainable from the hydrolysis of ' 
on treatment with acidified 
produces 
. ' 
' contains two different types of hydrogen atoms. The structure of ' A ' is
Text Solution
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Compound A undergoes bromination with aqueous 
to form B , which is soluble in dilute acid, indicating an amino group is present.
B undergoes diazotization with 
at 
to form diazonium compound C .
The diazonium compound is then treated with 
to form nitrile compound D .
Hydrolysis of D produces carboxylic acid E.
When A is treated with acidified 
, 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 , which is 2 -aminobenzoic acid, fits all these transformations.
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