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Amines
Question
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Method by which aniline cannot be prepared is 

  • hydrolysis phenyl isocyanide with the acidic solution

  • degradation of benzamide with bromine in alkaline solution

  • reduction of nitrobenzene with H2/Pd in ethanol

  • potassium salt of phthalimide treated with chlorobenzene followed by the hydrolysis with aqueous NaOH solution

Answer

D.

potassium salt of phthalimide treated with chlorobenzene followed by the hydrolysis with aqueous NaOH solution

Due to resonance in chlorobenzene C- Cl  bond accquires double bond chracter hence, C -Cl bond is inert towards nucleophile (phthalimide ion)

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