Discussion
The relative ease of dehydration of the following alcohols is
(i) Propan-2-ol (ii) Propan-1-ol (iii) 2-Methylpropan-2-ol
Answer: E
The order is (iii) \(\gt\) (i) \(\gt\) (ii).
Acid-catalysed dehydration goes through a carbocation, so its ease follows carbocation stability: tertiary \(\gt\) secondary \(\gt\) primary. 2-Methylpropan-2-ol is tertiary, propan-2-ol is secondary and propan-1-ol is primary.
The tertiary alcohol dehydrates with dilute acid at a lower temperature, while the primary alcohol needs concentrated acid and a higher temperature. Every other option puts the primary alcohol ahead of a more substituted one.
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