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NEETChemistryCarboxylic Acid Derivatives

An unknown alkene 'X' with molecular formula C₈H₁₆ undergoes reductive ozonolysis to yield two moles of a single compound 'Y'. Compound 'Y' gives a positive Iodoform test but fails to give a silver mirror with Tollens' reagent. Identify the IUPAC name of alkene 'X'.

Options

  1. A3,4-Dimethylhex-3-ene
  2. BOct-4-ene
  3. C2,5-Dimethylhex-3-ene
  4. D2,4,4-Trimethylpent-2-ene

Correct answer

A. 3,4-Dimethylhex-3-ene

Step-by-step solution

Since alkene 'X' gives two moles of a single compound 'Y' on reductive ozonolysis, 'X' must be a symmetrical alkene. Compound 'Y' does not give a silver mirror with Tollens' reagent, indicating it is a ketone, not an aldehyde. It gives a positive Iodoform test, which means it is a methyl ketone (contains a -COCH₃ group). Given the molecular formula of 'X' is C₈H₁₆ , compound 'Y' must have 4 carbon atoms ( C₄H₈O ). The only 4-carbon methyl ketone is butan-2-one ( CH₃COCH₂CH₃ ). Connecting two molecules of butan-2-on

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