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A mixture of 4-methylphenol and 4-methylcyclohexanol was run on a TLC plate using 3:1 hexane:ethyl acetate...

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Chemistry

A mixture of 4-methylphenol and 4-methylcyclohexanol was run ona TLC plate using 3:1 hexane:ethyl acetate as the eluent. Only onespot was seen using a UV lamp. Does this mean that both spots havethe same Rf or is there another explanation? How mightyou solve this problem?

Answer & Explanation Solved by verified expert
3.9 Ratings (524 Votes)
4methylphenol is more acid than 4methylcyclohexanol which in turn should lead us to conclude that 4methylphenol is more polar This is actually expected since the lone pair of Oatom can participate in resonance with the ring No such resonance stabilization is offered in 4methylcyclohexanol However on the TLC plate with 31 hexaneethyl    See Answer
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