organic chemistry

[ankita paul]

when anisole reacts with HI .Phenol is produced insted of iodobenzene -why?give reason.............

[MOHINI BELANI]

when anisole reacts with HI .Phenol is produced insted of iodobenzene -why?give reason.............

When anisole reacts with HI, phenol is produced becoz of steric hiderance nucleophile Iodide cannot attack the benzene ring and moreover the vond between carbon of benzene ring acquire partial double bond character due to resonance hence is difficult to break.

[sushovan]

Anisole is a aryl alkyl ether.....in presence of HI the alkyl-oxygen bond breaks down and form phenoxide ion which has better resonance stabilization.HI also breaks into H+ and I-. Now PhO- and H+ combines to form PhOH. I- also unable to attack in OCH3 bond of anisole due to its double bond charecter.
Ph-O-CH3+HI=PhOH+CH3I.....By further HI addition PhOH transfers into PhI(U may ask also -OH bond has double bond charecter..thats why i suggest you to mention about the aryl alkyl linkage). PhBr also perform this reacton but slower in rate.:p