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A cyclic hydrocarbon 'M' with the molecular formula C ₆ H ₁₀ yields 5 -oxohexanal on reductive ozonolysis. When 'M' is treated with HBr in the presence of benzoyl peroxide, it forms a major product 'P'. The IUPAC name of 'P' is :

Options

  1. A1 -bromo- 1 -methylcyclopentane
  2. B1 -bromo- 3 -methylcyclopentane
  3. C1 -bromo- 2 -methylcyclopentane
  4. D6 -bromohexan- 2 -one

Correct answer

C. 1 -bromo- 2 -methylcyclopentane

Step-by-step solution

The reductive ozonolysis of 'M' ( C ₆ H ₁₀ ) yields 5 -oxohexanal ( CH ₃ COCH ₂ CH ₂ CH ₂ CHO ). To deduce the structure of 'M', we connect the carbonyl carbons (C 1 of the aldehyde and C 5 of the ketone) with a double bond. This intramolecular ring closure results in a five-membered ring with a methyl group attached to one of the double-bonded carbons. Thus, 'M' is 1 -methylcyclopentene. When 1 -methylcyclopentene is treated with HBr in the presence of benzoyl peroxide, it undergoes anti-Markovnikov addition (pero

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