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Account for the following: (i) The boi...

Account for the following:
(i) The boiling points of alchols decrease with increase in branching of the alkyl chain.
(ii) Phenol does not give protonation reaction readily.
(iii) Phenyl methyl ehter reacts with HI to give phenol and methyl iodide and not iodobenzene and methyl alcohol.

Text Solution

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(i) The boiling point of alcohols decrease with increase in branching of alkyl chain: This is because of attraction decreases with decrease in surface area, hence boiling point decreases.
(ii) Phenol does not give protonation reaction readily: In phenols, the Ione pair of oxygen is being shared with benzene ring through resonance. Hence the electron density around oxygen is relatively less and therefore penols does not give protonation easily.
(iii) Phenyl methyl ether reacts with HI to give phenol and methyl iodide and not iodobenzene and methyl alcohol,

It is probably due to the fact that phenyl oxygen bond has a partial double bond character due to resonance. Therefore its cleavage is difficult as compared to alkyl oxygen bond.
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