Question

Method by which aniline cannot be prepared is:
A. hydrolysis phenyl isocyanide with acidic solution
B. degradation of benzamide with bromine in alkaline solution
C. reduction of nitrobenzene with `H_(2)//Pd` in ethanol
D. potassium salt of phthalimide treated with chlorobenzene followed by the hydrolysis with aqueous NaOH solution

Answer 1

Correct Answer - D
Due to resonance in chlorobenzene C-Cl bond acquires double bond character hence, C-Cl bond is inert towards nucleophile (phthalimide ion). Therefore aniline cannot be prepared.