Organic Chemistry Basics 2 Question 77

77. You have an ether solution containing 4-hydroxybenzoic acid and 4-aminobenzoic acid. Explain, how will you separate the two in not more than 3 steps? Give confirmatory tests with reagents and conditions for functional groups of each.

(2003)

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Solution:

(aqueous layer)

$\xrightarrow{\mathrm{FeCl}_{3}}$ violet colouration confirm phenolic group

$$ \xrightarrow{\mathrm{NaHCO}{3}} \mathrm{CO}{2} \uparrow \xrightarrow[\text { water }]{\text { lime }} \text { milky } \longrightarrow-\mathrm{COOH} $$