Benzyl chloride more reactive than chlorobenzene toward nsr
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hey mates,
We know that chloro benzene is resonance stabilized , if we look at the resonating structures ,

We can see that , the loan pair on chlorine participates in the resonance and hence forms a partial double bond. Therefore the loan pair of chlorine is not always available for reaction. Onthe other hand, benzyl chloride , has no resonance and the loan pair on chlorine is always available for reaction. Thus ,benzyl chloride is more reactive than chloro benzene.
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Avs Sharma, Balaji Study Circle (2001-present)
Answered Dec 20, 2017
In case of chlorobenzene,chlorine is directly attached to the sp² hybridised carbon of the ring. Chlorine is deactivating and ortho para directing.
Due to resonance C-Cl bond aqlcquires double bond characters. There is electronic repulsion between chlorobenzene and approaching nucleophile also.Phenyl cation is highly unstable,hence chlorobenzene is less reactive.
In case of benzyl chloride ,benzyl cation is highly stable due to resonance.Hence it gives nucleophilic substitution reactions by SN¹
We know that chloro benzene is resonance stabilized , if we look at the resonating structures ,

We can see that , the loan pair on chlorine participates in the resonance and hence forms a partial double bond. Therefore the loan pair of chlorine is not always available for reaction. Onthe other hand, benzyl chloride , has no resonance and the loan pair on chlorine is always available for reaction. Thus ,benzyl chloride is more reactive than chloro benzene.
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Avs Sharma, Balaji Study Circle (2001-present)
Answered Dec 20, 2017
In case of chlorobenzene,chlorine is directly attached to the sp² hybridised carbon of the ring. Chlorine is deactivating and ortho para directing.
Due to resonance C-Cl bond aqlcquires double bond characters. There is electronic repulsion between chlorobenzene and approaching nucleophile also.Phenyl cation is highly unstable,hence chlorobenzene is less reactive.
In case of benzyl chloride ,benzyl cation is highly stable due to resonance.Hence it gives nucleophilic substitution reactions by SN¹
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