[Methyl_Manic]

Hi Guys,

so im confused with the below question, i have ordered the functional groups below in what i think is the correct order for Basic -> less Basic, and the reason, however i have two conflicting answers. any help with this would be much appreciated!

Question: list the following functional groups in order of basicity: R-NH2, R-O(-), R-OH

my answer:
 R-O(-) > R-NH2 > R-OH
 basic -> less Basic

explanation: the definition of a lewis base is any species that donates a pair of electrons to a lewis acid, R-O(-) has extra negative charge and wants to get rid of it, R-OH oxygen is more electronegative than R-NH2 Nitrogen and wants to hold onto its electrons therefore less likely to be nucleophilic compared to Nitrogen.

however this is where im confused, Oxygen is "happy" with two lone pairs of electrons, Nitrogen is "happy" with one lone pair.. would Oxygen not have more lone pairs to donate, thus making it more basic?
 

[Dan]

Quantity is not the most important thing. Consider the "inert" gases for example.

[Babcock_Hall]

I would think in terms of the acidity (acid strength) of the conjugate acid of each of the three chemical species.  The strength of the acid is something that can be measured.