Give reason for following:
(i) O-nitrophenol is more acidic than o-methoxyphenol.
(ii) Butan-1-ol has a higher boiling point than diethyl ether
(iii) (CH3)3C-O-CH3 on reaction with HI gives (CH3)3C-I and CH3OH as main products and not (CH3)3C-OH and CH3I.
(i) Nitro group is an electron withdrawing group which decreases the electron density of phenol and shows –I effect and hence increase the acidity of phenol. Whereas OCH3 (methoxy) is an electron releasing group which shows +I effect and increases the electron density on Phenol ring and hence decreases its acidity.
(ii) Butanol is a polar molecule with a very strong intermolecular H bonding in H and OH group resulting in very strong bond and hence by, it has very high boiling point. On the other hand, no such strong H bonding is present in ether, so they have relatively very low boiling point.
(iii) Territory ethers when react with HI follows SN1 mechanism. And as 3° carbocation is more stable than 1° carbocation, I- attacks on it results in the formation of (CH3)3C-I and OH group acts on CH3+ and forms CH3OH.
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