Ncert Exercises & Solutions

Write the mechanism of the reactioni of HI with methoxybenzene.

In case of alkyl aryl ethers, the products are always phenol and an alkyl halide because due to resonance

C_{6} H_{5} - O

bond has partial double bond character. The mechanism is given below:

Mechanism: Protonation of anisole gives methylphenyl oxonium ion.

In this ion, the bond between O —CH₃, is weaker than the bond between $O - C_{6} H_{5}$ which has partial double bond character. This partial double bond character is due to the resonance between the lone pair of electrons on the O -atom and the ${sp}^{2}$ hybridised carbon atom of the phenyl group. Therefore, attack by $I^{-}$ ion exclusively breaks the weaker $O - {CH}_{3}$ bond forming methyl iodide and phenol.

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