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Alcohols Phenols and Ethers question

2003 · Shift 0 · Q16
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Alcohols Phenols and Ethers question

2003 · Shift 0 · Q16

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
During dehydration of alcohols to alkenes by heating with conc. H2SO4H_2SO_4H2​SO4​ the initiation step is
  1. A
    formation of carbocation
  2. B
    elimination of water
  3. C
    formation of an ester
  4. D
    protonation of alcohol molecule
View written solutionFree

Correct answer: D

  1. Reaction type

    Dehydration of an alcohol with concentrated H2SO4H_2SO_4H2​SO4​ is an acid-catalyzed elimination reaction that gives an alkene.

  2. What happens first?

    Alcohol contains the −OH-OH−OH group, but OH−OH^-OH− is a poor leaving group. So, before elimination can occur, the alcohol must be converted into a better leaving group.

  3. Initiation step

    In acidic medium, the lone pair on oxygen of the alcohol attacks a proton from the acid:

    R−OH+H+→R−OH2+R-OH + H^+ \rightarrow R-OH_2^+R−OH+H+→R−OH2+​

    This is protonation of the alcohol molecule.

  4. Why not the other options?

    • A: formation of carbocation — this may occur later (especially in 2∘2^\circ2∘ and 3∘3^\circ3∘ alcohols), but it is not the first step.
    • B: elimination of water — water leaves after protonation, so this is also not the initiation step.
    • C: formation of an ester — not the initiating step in alkene formation by dehydration.
    • D: protonation of alcohol molecule — correct, because this is the first event that activates the alcohol.
  5. Conclusion

    The initiation step is:

    Protonation of alcohol molecule\boxed{\text{Protonation of alcohol molecule}}Protonation of alcohol molecule​

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