InterviewSolution
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InterviewSolution
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(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 |
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Answer» Solution :(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)` |
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