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How are the following conversions accomplished (1) Aniline to chlorobenzene (2) Nitrobenzene to phenol
why chlorobenzene is less reactive towards nucleophilic substitution reaction towards nucleophilic reaction???? In chlorobenzene, the electron pair of chlorine atom is in conjugation with π electrons of benzene ring. Thus, chlorobenzene is a resonance hybrid of the following structures:The contributing structures III, IV and V indicate that C-Cl bond has partial double character.As a result, the C-Cl bond in chlorobenzene is shorter and hence, stronger.Thus, cleavage of C-Cl bond in benzene becomes difficult which makes it less reactive towards nucleophilic substitution.