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

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) The reaction of methoxybenzene (anisole) with $HI$ proceeds via an $S_N2$ mechanism. The steps are as follows:
Step $1$: Protonation of the ether oxygen atom.
The lone pair on the oxygen atom of methoxybenzene attacks the proton $(H^+)$ from $HI$ to form a protonated ether (oxonium ion).
$C_6H_5-O-CH_3 + H^+ \rightleftharpoons C_6H_5-O^+(H)-CH_3$
Step $2$: Nucleophilic attack by the iodide ion $(I^-)$.
The iodide ion $(I^-)$ acts as a nucleophile and attacks the less sterically hindered methyl carbon atom of the protonated ether. This leads to the cleavage of the $C-O$ bond,resulting in the formation of phenol and methyl iodide $(CH_3I)$.
$C_6H_5-O^+(H)-CH_3 + I^- \xrightarrow{S_N2} C_6H_5-OH + CH_3I$

Explore More

Similar Questions

In which of the following reactions is the product obtained $t-$butyl methyl ether?

Which of the following is an appropriate set of reactants for the preparation of $1-methoxy-4-nitrobenzene$ and why?

Difficult
View Solution

Which of the following mixtures is obtained when $tert$-butyl methyl ether is heated with $HI$?

Difficult
View Solution

Assertion: Ethers behave as bases in the presence of mineral acids.
Reason: Due to the presence of lone pairs of electrons on oxygen.

Identify the products $R$ and $S$ in the reaction sequence given:
$(CH_3)_3 COH$ $\xrightarrow{Na} P$ $\xrightarrow{CH_3 Br} Q$ $\xrightarrow[\Delta]{HI} R + S$

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo