(a) Out of t-butyl alcohol and n-butanol, which one will undergo acid catalysed dehydration faster and why?
(b) Carry out the following conversions:
(i) Phenol to Salicylaldehyde
(ii) t-butylchloride to t-butyl ethyl ether
(iii) Propene to Propanol

Explanation

(a) t-butyl alcohol will undergo acid catalysed dehydration faster. This is because the tertiary carbonium ion formed with t-butyl alcohol is more stable than primary carborium ion formed with n-butanol.
`underset("t-Butyl chloride")(CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-Cl)overset(NaOH)tounderset("t-Butyl alcohol")(CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-OH)overset(Na)toCH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-ONa overset(CH_(3)CH_(2)Cl)tounderset("t-Butylethyl ether")(CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-OCH_(2)CH_(3))+NaCl`
(b) (i) Phenol to Salicylaldehyde

(ii) t-butylchloride to t-butyl ethyl ether
`CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-O^(-)Na^(+)+CH_(3)CH_(2)Cl tounderset("t-Butylethyl ether")(CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-O-CH_(2)CH_(3))`
(iii) Propene to Propanol
`underset("Propene")(CH_(3)-CH=CH_(2)) underset("Peroxide")overset("HBr")to CH_(3)-CH_(2)-CH_(2)Br overset(NaOH)to underset("Propanol")(CH_(3)CH_(2)CH_(2)OH)`