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 (109∘28′).
(iii) (CH3)3C−O−CH3 on reaction with HI gives (CH3)3C−IandCH3−OH as the main products and not (CH3)3C−OHandCH3−I.
(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 −C−O−H 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)3C−I and CH3OH formed on treatment of HI with −(CH3)3−CO−CH3.
MeC−O−Me→Me3C++MeO−+HI→Me3C−I+MeOH