JEE MainChemistryGeneral Organic Chemistry
Which of the following cyclic ketones will form an oxime that exhibits geometrical isomerism upon reaction with hydroxylamine?
Options
- A4-Ethylcyclohexanone
- B4,4-Dimethylcyclohexanone
- C3-Methylcyclohexanone
- 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