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MHT CET202525 Apr 2025Morning ShiftChemistryAlcohols Phenols and EthersActual

Which of the following forms 2-Methylbut-2-ene on heating with concentrated sulphuric acid?

Options

  1. AButan-2-ol
  2. B2-Methyl-2-propanol
  3. C2-Methylbutan-1-ol
  4. D2-Methylbutan-2-ol

Correct answer

D. 2-Methylbutan-2-ol

Step-by-step solution

Target Product: 2-Methylbut-2-ene CH₃-C(CH₃)=CH-CH₃ Dehydration of alcohols with concentrated H₂ SO₄ proceeds via an E1 mechanism, forming carbocations that undergo elimination following Zaitsev's rule. Butan-2-ol yields but-2-ene as the major product, not the target compound. 2-Methyl-2-propanol dehydrates to form 2-methylpropene. 2-Methylbutan-1-ol undergoes dehydration with carbocation rearrangement: the primary carbocation CH₃-CH₂-CH(CH₃)-CH₂+ rearranges via 1,2-hydride shift to form the tertiary carbocation CH

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