- A1- Pentanol
- B4-Hydroxypentan - 2-one
- C3-Hydroxypentan - 2-one
- D2-Hydroxycyclopentanone
View written solutionFree
Correct answer: C
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Principle involved: acid-catalyzed dehydration of alcohols
Under acidic conditions, alcohols lose water to form alkenes. The ease of dehydration depends mainly on the stability of the intermediate/cation-like transition state and on whether the product alkene is especially stabilized. -
Key idea for -hydroxy carbonyl compounds
Compounds containing the pattern or, more generally, a -hydroxy carbonyl system, dehydrate very easily under acidic conditions because they give an -unsaturated carbonyl compound, which is strongly stabilized by conjugation. -
Examine each option
Option A: 1-Pentanol
Structure: This is a simple primary alcohol. Its dehydration requires harsher conditions because it does not gain any special stabilization in the alkene product.
So, not the most readily dehydrated.
Option B: 4-Hydroxypentan-2-one
Structure: Here the is at the -position relative to the carbonyl, not the -position. Dehydration would not directly give a conjugated -unsaturated ketone in the most straightforward way.
Hence, it is not especially activated for easy dehydration.
Option C: 3-Hydroxypentan-2-one
Structure: Here the is on the -carbon relative to the carbonyl group. This is a -hydroxy ketone. On dehydration, it forms: which is an -unsaturated ketone, stabilized by conjugation.
Therefore, this compound dehydrates very readily under acidic conditions.
Option D: 2-Hydroxycyclopentanone
This is also an -hydroxy ketone (the is adjacent to the carbonyl). Dehydration here would not be as straightforward/favorable as in a -hydroxy carbonyl leading to a conjugated enone.
So, it is less readily dehydrated than option C.
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Conclusion
The compound that most readily undergoes dehydration is the one that forms a conjugated enone most directly, i.e. 3-hydroxypentan-2-one.
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Comparison with stored answer
Stored correct answer: B
Derived answer: CThese do not match. The likely reason is that option C is the true -hydroxy ketone, which dehydrates most easily to an -unsaturated ketone. Option B is a -hydroxy ketone and does not enjoy the same direct conjugation-driven dehydration advantage.
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