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Question

What is aromatic nucleophilic substitution reaction?


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Solution

1. Nucleophilic substitution occurs when the reactant is attacked by a nucleophile and its hydrogen is replaced and substituted by the attacking nucleophile.

2. In aromatic nucleophilic substitution, the aromatic ring is substituted by a nucleophile by replacing a hydrogen atom or any other substituent present in the ring.

3. Aromatic rings undergoing nucleophilic substitution is not easy due to the presence of electron cloud above and below the ring, it behaves as a nucleophile and can thus undergo electrophilic substitution easily.

4. The leaving group attached to the benzene ring, possesses double bond or a lone pair of electron can cause delocalization of charges in the ring. This leads to the formation of a partial double bond between the leaving group and benzene ring. This makes the nucleophilic substitution less feasible.

5. Thus, to enhance the nucleophilic substitution of the aromatic ring, electron withdrawing groups should be present on the ring as substituent which reduces the nucleophilic nature of the ring. The presence of heteroatoms like N,O,S etc as a part of the ring also helps to enhance the aromatic nucleophilic substitution.


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