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  • Write the mechanism of the reaction of HI with methoxybenzene.

Write the mechanism of the reaction of HI with methoxybenzene.

 

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Phenol and an alkyl halide are always the products of alkyl aryl ethers because C_{6}H_{5}-O bond has a partial double bond character when resonance takes place.

Mechanism :

Step 1 – The protonation of ether molecules forms a methylphenyl oxonium ion

The above-mentioned ion has a weaker O-CH_{3} bond as compared to the O-C_{3}H_{5} as it has a partial double bond character. This double bond character is exhibited due to the resonance between the lone pair of electrons present on O-atom and the carbon atom of the phenyl group, which is sp^{2} hybridised.

Step 2 – The protonated ether gives methyl iodide and phenol after interacting with I ion in SN^{2} mechanism.

 

 

 

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