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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

Consider the following reaction sequence: HO - CH ₂- CH = CH ₂ [ (ii) NaHSO ₃] (i) OsO ₄ (A) KHSO ₄, (B) The major product (B) is:

Options

  1. AH ₂ C = CH - CH ₂- OH
  2. BH ₂ C = C = CH ₂
  3. CH ₂ C = CH - COOH
  4. DH ₂ C = CH - CHO

Correct answer

D. H ₂ C = CH - CHO

Step-by-step solution

The starting material is allyl alcohol, HO - CH ₂- CH = CH ₂ . Reaction with OsO ₄ followed by NaHSO ₃ causes syn-dihydroxylation of the carbon-carbon double bond. This yields glycerol, HO - CH ₂- CH ( OH )- CH ₂- OH as product (A). Heating glycerol with a dehydrating agent like KHSO ₄ results in the elimination of two molecules of water. This dehydration process yields acrolein, H ₂ C = CH - CHO as the major product (B). Answer: H ₂ C = CH - CHO

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