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Consider the compounds 4-tert-butylcyclohexanol and 4- tert-butylcyclohexanone. Using silica gel plates, which of the two compounds...

Consider the compounds 4-tert-butylcyclohexanol and 4- tert-butylcyclohexanone. Using silica gel plates, which of the two compounds will have the higher Rf value when ethyl acetate is the developing solvent? Which will have the higher Rf value when dichloromethane is the developing solvent? Give your reasoning in each case.

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Answer #1

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In both compounds, 4-tert-butylcyclohexanol is more polar than that of 4- tert-butylcyclohexanone because the alcohol group is more polar and ketone group is relatively less polar than alcohol group.

Thus, in ethyl acetate solvent, the Rf value for 4- tert-butylcyclohexanone​ is higher than that of 4-tert-butylcyclohexanol​ while in methylene dichloride solvent, the Rf value for 4- tert-butylcyclohexanone​ is higher than that of 4-tert-butylcyclohexanol​​ and greater than the Rf observed in ethyl acetate.

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