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Write the mechanism of the reaction of H...

Write the mechanism of the reaction of HI with methoxybenzene.

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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.
`C_(6)H_(5)-underset(..)overset(..)(O)CH_(3)+H^(+) rarr C_(6)H_(5)-underset(H)underset(|)overset(+)(O):-CH_(3)`
In this ion, the bond between `O-CH_(3)` is weaker than the bond between `O-C_(6)H_(5)` which has partial double bond character. The 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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NCERT EXEMPLAR-ALCOHOLS, PHENOLS AND ETHERS-Alcohols, Phenols And Ethers
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  2. Arrange water, ethanol and phenol in increasing order of acidity and g...

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  4. Match the starting material given in Column I with the products formed...

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  5. Match the items of Column I with items of Column II.

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  6. Match the items of Column I with items of Column II.

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  7. Assertion (A) Addition reaction of water to but-1-ene in acidic medium...

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  8. Assertion (A) p-nitrophenol is more acidic than phenol. Reason (R) N...

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  9. Assertion (A) IUPAC name of the compound CH(3)-underset(CH(3))unders...

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  10. Assertion (A) Bond angle is ethers is slightly less than tetrahedral a...

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  11. Assertion (A) Boiling points of alcohols and ethers are high. Reason...

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  12. Assertion (A) Like bromination of benzene, bromination of phenol is al...

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  13. Assertion (A) o-nitrophenol is less soluble in water than the m and p-...

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  14. Assertion (A) Ethanol is a weaker acid than phenol. Reason (R) Sodiu...

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  15. Assertion (A) Phenol forms 2, 4, 6-tribromophenol o treatement with Br...

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  16. Assertion (A) Phenols give o-and p-nitrophenol on nitration with conc....

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

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  18. (a) Name the starting material used in the industrial preparation of p...

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  19. How can phenol be converted to aspirin ?

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