Which of the following compounds will most readily be dehydrated to give alkene under acidic condition?
A
2-Hydroxycyclopentanone
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B
1-Pentanol
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C
3-Hydroxypentan-2-one
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D
4-Hydroxypentan-2-one
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Solution
The correct option is D 4-Hydroxypentan-2-one 3-Hydroxypentan-2-one and 4-Hydroxypentan-2-one will most readily be dehydrated to give alkene under acidic condition. This will lead to formation of α−β unsaturated ketone. But out of both 4-Hydroxypentan-2-one will most readily be dehydrate to give alkene under acidic condition. Note: Dehydration of 2-Hydroxycyclopentanone will lead to C=C double bond in 5 member ring that will cause strain and product is less likely to be formed.