Which of the following is not the product of dehydration of [figure]
- [figure]
- [figure]
- [figure]
- [figure]
Answer
(1) [figure]
Solution
The given alcohol, 2-cyclohexylbutan-2-ol, has 10 carbon atoms. Dehydration removes only H2O, so every product must also have 10 carbon atoms.
On heating with acid, a 3° carbocation is formed:
[figure]
Loss of a β-hydrogen from the ring CH, the CH2 group or the CH3 group gives the alkenes in options (3), (2) and (4) respectively (each with 10 carbon atoms).
∵ The compound in option (1) carries two methyl groups on the side-chain carbon, it has 11 carbon atoms.
∴ It cannot be formed by dehydration of the given alcohol.
Answer: (1)