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Anisole on reaction with HI produces only phenol and methyl iodide. Give a reason?

Answer
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Hint: In organic chemistry, the electrophilic substitution reactions are the type of chemical reactions in which an electrophile displaces a group in a compound. This reaction involves the initial attack of an electrophile followed by the reaction with a nucleophile in order to form the final product. Most of the aromatic compounds undergo electrophilic substitution reactions due to the nucleophilic nature of the benzene ring.

Complete answer:
The reaction mechanism for the given substitution reaction is as follows:
Step-1: Dissociation of hydrogen iodide takes place into hydrogen and iodide ions respectively. The reaction is as follows:
HIH++I
Step-2: The lone pair present on the oxygen atom of the anisole will act as a nucleophile and an attack of hydrogen ion will take place. The reaction proceeds as follows:
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Step-3: Iodide ions will attack the methyl group and formation of phenol and methyl iodide will take place. The reaction proceeds as follows:
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In the reaction process, only phenol and methyl iodide are formed because the bond between OCH3 is weaker as compared to OC6H5 due to the presence of partial double bond character. Therefore, when iodide ion attacks the cleavage of OCH3 bonds take place to form methyl iodide instead of cleavage of OC6H5 to form iodobenzene and methyl alcohol.
Note:
It is important to note that phenols do not further react to give halides because the carbon atoms of the ring are sp2 hybridized and consist of a cloud of pi electrons over the bonds. So, it cannot undergo a nucleophilic substitution reaction to form respective halides.