Discuss the mechanism of chlorination of benzene. from Chemistr

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 Multiple Choice QuestionsLong Answer Type

234.

Discuss the mechanism of electrophilic substitution reactions of benzene?

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235. Discuss the mechanism of chlorination of benzene.


Mechanism of chlorination of benzene: Benzene on treatment with chlorine in the presence of halogen carrier (Fe or FeCl3) forms chlorobenzene.



Different steps involved in the mechanism are:
(i) Generation of an electrophile (Cl+): The catalyst Lewis acid (FeCl3) helps in the generation of an electrophile (Cl+) by causing polarisation of the chlorine molecule.



(ii) Formation of the carbocation: The electrophile (Cl+) attacks the benzene ring to form an intermediate carbocation which is resonance stabilised. It is a slow step.



Resonance hybrid of the above resonating structures can be represented as,



(iii) Proton transfer from the carbocation to form chlorobenzene. 



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239.

Why does benzene undergo electrophilic substitution reactions easily and nucleophilic substitutions with difficulty?

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