Basicity / Acidity of Cycloalkanes

[drill-and-fill]

When comparing the basicity or acidity of a cyclohexane, can you just compare what kind of substituents are attached to each choice?

For aromatic rings, I know that EWG increase acidity of the ring while EDG increase basicity.

Does the same rule apply to cyclohexanes as well? For example, if you have a cyclohexane with just an amine vs cyclohexane with an amine with two methyl groups, would the latter one be more basic?

Thanks in advance.

---

Members don't see this ad.

 

[BRZ24]

When comparing the basicity or acidity of a cyclohexane, can you just compare what kind of substituents are attached to each choice?

For aromatic rings, I know that EWG increase acidity of the ring while EDG increase basicity.

Does the same rule apply to cyclohexanes as well? For example, if you have a cyclohexane with just an amine vs cyclohexane with an amine with two methyl groups, would the latter one be more basic?

Thanks in advance.

In general, if you are ranking acid or bases, use the CARDIO rule.

When ranking phenol, that is a benzene with an OH group. You rank its conjugate base and if there is a EWG present that it will increase the acidity by stabilizing the base. Vice versa with EDG.

However, you can't assume the EWG and EDG rule for every bases out there. EWG and EDG rule works for phenol because its conjugate base is negatively charged.