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Question

Why preparation of aryl iodide by electrophillic substitution requires presence of an oxidising agent? why can arylflouride not be prepared by this method?

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Solution

During the electrophilic substitution of aromatic hydrocarbon, HI is produced during the reaction.Since it is a good reducing agent, it reduces the aryl iodide back to the aromatic hydrocarbon and iodine i.e the reaction is reversible.Therefore, oxidising agents such as HNO3, HgO etc. are used to remove HI produced in the reaction as follows:

4HI + 2 HNO3→ 2N2O3 + 3H2O + 2I2

Arylfluorides, cannot be prepared by this method due to high reactivity fluorine since the reaction is very violent.


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