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Aldehydes Ketones and Carboxylic Acids question

2018 · 16 Apr · Shift 1 · Q13
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Aldehydes Ketones and Carboxylic Acids question

2018 · 16 Apr · Shift 1 · Q13

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Which of the following compounds will most readily be dehydrated to give alkene under acidic condition ?
  1. A
    1- Pentanol
  2. B
    4-Hydroxypentan - 2-one
  3. C
    3-Hydroxypentan - 2-one
  4. D
    2-Hydroxycyclopentanone
View written solutionFree

Correct answer: C

  1. 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.

  2. Key idea for β\betaβ-hydroxy carbonyl compounds
    Compounds containing the pattern \ce−CO−CH(OH)−\ce{-CO-CH(OH)-}\ce−CO−CH(OH)− or, more generally, a β\betaβ-hydroxy carbonyl system, dehydrate very easily under acidic conditions because they give an α,β\alpha,\betaα,β-unsaturated carbonyl compound, which is strongly stabilized by conjugation.

  3. Examine each option

    Option A: 1-Pentanol

    Structure: \ceCH3−CH2−CH2−CH2−CH2OH\ce{CH3-CH2-CH2-CH2-CH2OH}\ceCH3−CH2−CH2−CH2−CH2OH 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: \ceCH3−CO−CH2−CH(OH)−CH3\ce{CH3-CO-CH2-CH(OH)-CH3}\ceCH3−CO−CH2−CH(OH)−CH3 Here the \ceOH\ce{OH}\ceOH is at the γ\gammaγ-position relative to the carbonyl, not the β\betaβ-position. Dehydration would not directly give a conjugated α,β\alpha,\betaα,β-unsaturated ketone in the most straightforward way.

    Hence, it is not especially activated for easy dehydration.

    Option C: 3-Hydroxypentan-2-one

    Structure: \ceCH3−CO−CH(OH)−CH2−CH3\ce{CH3-CO-CH(OH)-CH2-CH3}\ceCH3−CO−CH(OH)−CH2−CH3 Here the \ceOH\ce{OH}\ceOH is on the β\betaβ-carbon relative to the carbonyl group. This is a β\betaβ-hydroxy ketone. On dehydration, it forms: \ceCH3−CO−CH=CH−CH3\ce{CH3-CO-CH=CH-CH3}\ceCH3−CO−CH=CH−CH3 which is an α,β\alpha,\betaα,β-unsaturated ketone, stabilized by conjugation.

    Therefore, this compound dehydrates very readily under acidic conditions.

    Option D: 2-Hydroxycyclopentanone

    This is also an α\alphaα-hydroxy ketone (the \ceOH\ce{OH}\ceOH is adjacent to the carbonyl). Dehydration here would not be as straightforward/favorable as in a β\betaβ-hydroxy carbonyl leading to a conjugated enone.

    So, it is less readily dehydrated than option C.

  4. Conclusion
    The compound that most readily undergoes dehydration is the one that forms a conjugated enone most directly, i.e. 3-hydroxypentan-2-one.

Option C\boxed{\text{Option C}}Option C​

  1. Comparison with stored answer
    Stored correct answer: B
    Derived answer: C

    These do not match. The likely reason is that option C is the true β\betaβ-hydroxy ketone, which dehydrates most easily to an α,β\alpha,\betaα,β-unsaturated ketone. Option B is a γ\gammaγ-hydroxy ketone and does not enjoy the same direct conjugation-driven dehydration advantage.

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