Q67E

Question

Draw resonance structures of the intermediate carbocations in the bromination of naphthalene, and account for the fact that naphthalene undergoes electrophilic substitution at C1 rather than C2.

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Answer

There are seven resonating structures from C₁ :

There are six resonating structures from C₂ :

1Resonating structures

The structure formed by the delocalization of the pi electrons in the ring is called Lewis acid structure.

2Resonating structures at C1

On the reaction of the naphthalene with the bromine and bromination occur at C1 seven resonating structures are formed and out of which the first four resonating structure have a second ring which is fully aromatic and in the last three structures the positive charge is induced in the second aromatic ring and disturb the aromaticity of the compound as shown below:

Q66E

Q68E

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