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Mobile App Chapter 16: Q2P (page 486)
Propose a mechanism for the electrophilic fluorination of benzene with.
Short Answer
Formation of fluorobenzene
Step by step solution
Electrophilic substitution
In electrophilic aromatic substitution reactions, the hydrogen atom present in the aromatic ring is replaced by an electrophile.
The pi-electron of benzene attacks the fluorine ofand the non-aromatic intermediates losses – H to give the fluorinated product.
Mechanism
The mechanism begins with the aromatic ring attacking the fluorine atom bound to nitrogen in . This is because this fluorine is the most electrophilic atom. With this attack, we generate structure 2 which upon reacting with base rearomatizes to give the final product, fluorobenzene. The mechanism is as follows:
Formation of fluorobenzene
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Benzanilide