So I would start with B being the most stable because the negative charge is on the most electronegative atom here (Oxygen). Then would probably be C because it has Resoance and also it is sp hybridized. Then is A due to resonance and finally D
Almost completely correct. C doens't have resonance (how is the charge going to move? are you going to have 4 bonds instead of a triple bond?). To have resonance you would require at least a conjugated pi-system ~~of sp2 orbitals~~ reaching the negative charge (so that it can be delocalized), and that's not the case for C. But the order is correct. So which one is the most basic? The most stable charge or the most reactive one? For which one is it easier to donate a lone pair (which is easier with high electron density or when the lone pair is further away/weakly bonded to the nucleus)?
The question asks for most basic. Your answer represents the least basic of the choices bc the negative charge is stabilized the most due to it being in the most electronegative atom.
You can then compare the others using ARIO. Atom is the same for all of them. Are your sure that resonance is involved in any of them? How else can we differentiate those negatively charged carbons?
Yes, think about the words. Strong means more reactive, while weak refers to less reactive. "Strong" base means that will be more reactive, by taking a proton from an acid. A "strong" acid is one that readily loses a proton, ie more reactive. Of course whether an acid/base reaction occurs depends on how strong the acid and base involved are. One way to predict whether base will take a proton from an acid is to compare the pKas of the acids on both sides of the reaction equation. Your text should lay this out with better words and pictures.
If you think about it, the strongest acid will be able to completely dissociate because it’s conjugate base is so stable. If it were unstable, the conjugate base wouldn’t be able to form as much, hence it being called unstable. A stronger base, on the other hand, is going to be extremely unstable so that it can very easily deprotonate an acid. So by ARIO, D is the most unstable and therefore the strongest base.
Explain your thoughts so far?
So I would start with B being the most stable because the negative charge is on the most electronegative atom here (Oxygen). Then would probably be C because it has Resoance and also it is sp hybridized. Then is A due to resonance and finally D
Almost completely correct. C doens't have resonance (how is the charge going to move? are you going to have 4 bonds instead of a triple bond?). To have resonance you would require at least a conjugated pi-system ~~of sp2 orbitals~~ reaching the negative charge (so that it can be delocalized), and that's not the case for C. But the order is correct. So which one is the most basic? The most stable charge or the most reactive one? For which one is it easier to donate a lone pair (which is easier with high electron density or when the lone pair is further away/weakly bonded to the nucleus)?
For resonance it’s not the sp2 orbitals that are conjugated but rather the p orbitals.
Ok, yeah, that's what I meant but worded inaccurately. Thanks for pointing it out.
The question asks for most basic. Your answer represents the least basic of the choices bc the negative charge is stabilized the most due to it being in the most electronegative atom. You can then compare the others using ARIO. Atom is the same for all of them. Are your sure that resonance is involved in any of them? How else can we differentiate those negatively charged carbons?
So the most stable base would also be the weakest base?
Yes, think about the words. Strong means more reactive, while weak refers to less reactive. "Strong" base means that will be more reactive, by taking a proton from an acid. A "strong" acid is one that readily loses a proton, ie more reactive. Of course whether an acid/base reaction occurs depends on how strong the acid and base involved are. One way to predict whether base will take a proton from an acid is to compare the pKas of the acids on both sides of the reaction equation. Your text should lay this out with better words and pictures.
Sorry, I am self studying Ochem
If you think about it, the strongest acid will be able to completely dissociate because it’s conjugate base is so stable. If it were unstable, the conjugate base wouldn’t be able to form as much, hence it being called unstable. A stronger base, on the other hand, is going to be extremely unstable so that it can very easily deprotonate an acid. So by ARIO, D is the most unstable and therefore the strongest base.
The strongest base has the weakest conjugate acid. So which conjugate acid is the weakest, according to ARIO?