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Question

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 $$\alpha - \beta$$ 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.
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Chemistry

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