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Which of the following cycloalkenes, upon reductive ozonolysis, yields a product that gives both a positive iodoform test and a positive Tollens' test?

Options

  1. A1-methylcyclohexene
  2. B1,2-dimethylcyclohexene
  3. C3-methylcyclohexene
  4. D1-phenylcyclohexene

Correct answer

A. 1-methylcyclohexene

Step-by-step solution

To give a positive Tollens' test, the product must contain an aldehyde group ( -CHO ). To give a positive iodoform test, the product must contain a methyl ketone group ( -COCH₃ ). Let us evaluate the reductive ozonolysis product for each option: 1-methylcyclohexene undergoes reductive ozonolysis to yield 6-oxoheptanal ( CH₃-CO-CH₂-CH₂-CH₂-CH₂-CHO ). This molecule contains both a methyl ketone and an aldehyde group, so it will give both tests positive. 1,2-dimethylcyclohexene yields octane-2,7-dione ( CH₃-CO-CH₂-CH₂

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