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Does the delocalisation of the lone pair of electrons in the NH2 group mean that they are less available to attack the carbon making the 4-aminocyclohexanol more reactive? Or does the polarisation of the neighbouring molecule due to the higher electron density of the benzene ring make the 4-aminophenol more reactive?

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  • $\begingroup$ p-Anisidine and DMAP are especially nucleophilic specifically because of the resonance caused by situations like what you describe. That's also why they're so toxic. Not an answer, but certainly related. $\endgroup$ – SendersReagent Mar 5 '16 at 18:38
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4-aminocyclohexanol should be more reactive towards acetylation because the reactivity depends on the availability of the lone pair on N to be able to attack the C atom during acetylation. Since in 4-aminophenol the lone pair resonates in the benzene ring, its availability to attack will get reduced making it lesser reactive towards acetylation.

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