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An unknown straight-chain diol X ( C₄H₁₀O₂ ) is heated with concentrated H₂SO₄ to yield a hydrocarbon Y . Reductive ozonolysis of Y produces two moles of formaldehyde and one mole of glyoxal. The IUPAC name of diol X is:

Options

  1. AButane-1,4-diol
  2. BButane-1,2-diol
  3. CButane-2,3-diol
  4. DButane-1,3-diol

Correct answer

D. Butane-1,3-diol

Step-by-step solution

Reductive ozonolysis of hydrocarbon Y yields two moles of formaldehyde ( HCHO ) and one mole of glyoxal ( OHC-CHO ). Working backwards, the structure of Y is obtained by joining the carbonyl carbons with double bonds: CH₂=O + O=CH-CH=O + O=CH₂ CH₂=CH-CH=CH₂ Thus, Y is 1,3-butadiene. Diol X is a straight-chain compound with the formula C₄H₁₀O₂ that undergoes dehydration to form 1,3-butadiene. Let us examine the dehydration of the given straight-chain diols: Butane-1,4-diol undergoes intramolecular dehydration to for

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