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Question:

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

2-Hydroxycyclopentanone

3-Hydroxypentan-2-one

1-Pentanol

4-Hydroxypentan-2-one

Solution:

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−βunsaturated 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.