3
$\begingroup$

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?

$\endgroup$
1
  • $\begingroup$ 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. $\endgroup$ Mar 5, 2016 at 18:38

1 Answer 1

1
$\begingroup$

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.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge that you have read and understand our privacy policy and code of conduct.

Not the answer you're looking for? Browse other questions tagged or ask your own question.