6.3 qualitative estimates of acidity Flashcards
anything that shift equilibrium away form the acid…
increases relative acidity
(stabilize the products; destabilize the starting material
what is the best way to predict relative strength of a neutral acid
by looking at the stability of its conj base
what are some stabilizing features of conj base
resonance, inductive, electronegativity, size
anything that stabilizes the conj base, especially things that stabilize the neg formal charge…
increase acidity
generally the strongest acids have…
very stable conj base
the more electronegitive an atom is…
the better it can stabilize extra electron density
when comparing to acids (other factors being =) the acid with the more electro- atom becoming antionic will be more…
acidic
what do inductive effects do
if there are electroneg atoms near by. they pull electron density away making that anion more stable
what does the strength of induction depend on
electronegativity, number of atoms and proximity
how does size effect electron density
they larger an atom and its orbitals are the better it can stabilize extra alectron density
(when other factors are equal) the acid with the larger atom becoming anionic will be…
more acidic (only in the same column of periodic table
(when other factors are equal) the acid with more “s character” at the atom carrying the H will be…
more acidic
if the electron density on the conjugate base can be delocalized by resonance than the conj base is…
much more stable
when compairing two acids (with other factors =) the acid with more delocalization of the anion will be…
more acidic
when comparing two acids if you have residence that isnt delocalizing of the charge what does this do
nothing only important if resonance is delocalizing the charge
