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Question

Give reasons of the following.
(i) Phenol is more acidic than methanol.
(ii) The C-O-H bond angle in alcohols is slightly less than the tetrahedral angle (10928).
(iii) (CH3)3COCH3 on reaction with HI gives (CH3)3CIandCH3OH as the main products and not (CH3)3COHandCH3I.

Solution
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(1) Phenoxide ion is more stabilized than CH3O ion through resonance. Thus, phenol is more acidic than methanol.
(2) Due to extensive intermolecular H-bonding the COH bond angle in alcohol slightly less than tetrahedral angle. H-bond thrust the angle slightly.
(3) Since, (CH)3C+ is more stabilized through +I effect of three methyl group thus (CH3)3CI and CH3OH formed on treatment of HI with (CH3)3COCH3.
MeCOMeMe3C++MeO+HIMe3CI+MeOH

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(ii) The C-O-H bond angle in alcohols is slightly less than the tetrahedral angle (10928).
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