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JEE MainChemistryGeneral Organic Chemistry

Which of the following cyclic ketones will form an oxime that exhibits geometrical isomerism upon reaction with hydroxylamine?

Options

  1. A4-Ethylcyclohexanone
  2. B4,4-Dimethylcyclohexanone
  3. C3-Methylcyclohexanone
  4. DCyclohexanone

Correct answer

C. 3-Methylcyclohexanone

Step-by-step solution

For an oxime ( >C=N-OH ) to exhibit geometrical isomerism, the two groups attached to the carbon atom of the C=N bond must be different. In the case of cyclic ketones, this implies that the two paths around the ring starting from the carbonyl carbon must be non-identical. Let us examine the given ketones: 1. 4-Ethylcyclohexanone: The paths from C1 to C4 are identical (symmetric with respect to the plane passing through C1 and C4). Thus, the oxime will not show geometrical isomerism. 2. 4,4-Dimethylcyclohexanone: Si

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