Solved: CHEMISTRY Question for NEET

NEET CHEMISTRYMedium

Which of the following is produced when anisole reacts with HI?

Benzaldehyde and ethanol

Acetophenone

Iodobenzene and methanol

Phenol and methyl iodide

Reactants: Anisole is methyl phenyl ether ( $C_6H_5-O-CH_3$ ). HI is Hydrogen Iodide.
Mechanism: The reaction involves the cleavage of the ether linkage. In alkyl aryl ethers, the oxygen atom is attached to a benzene ring. The lone pair on the oxygen enters into resonance with the benzene ring, imparting a partial double bond character to the $C_{phenyl}-O$ bond. This makes the $C_{phenyl}-O$ bond much stronger and difficult to break compared to the $C_{methyl}-O$ bond.
Cleavage: Consequently, the weaker $O-CH_3$ bond breaks. The proton ( $H^+$ ) from HI protonates the oxygen.
Nucleophilic Attack: The iodide ion ( $I^-$ ) attacks the smaller alkyl group (methyl group) via an $S_N2$ mechanism.
Products: This results in the formation of Phenol ( $C_6H_5OH$ ) and Methyl Iodide ( $CH_3I$ ).
Conclusion: The products are Phenol and methyl iodide.

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