Question

Which of the following compounds will most readily be dehydrated to give alkene under acidic condition?

A

2-Hydroxycyclopentanone

B

1-Pentanol

C

3-Hydroxypentan-2-one

D

4-Hydroxypentan-2-one

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Solution
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Correct option is D)

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 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 double bond in 5 member ring that will cause strain and product is less likely to be formed.

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