Influence of electronic and structural effects on acidity Flashcards
what happens when there’s an increase in pKa (increase in electronegativity)?
increase in acidity
more stabilization of conjugate base
what are the inductive effects of electrons being withdraw in an equilibirum?
stabilizing of the molecule
what is the inductive effect of electrons being donated in an equilibrium?
destabilizing of the molecule
what do electron withdrawing groups do to the acidity?
increase it
what does increasing the halogen atom do to the acidity?
increase in acidity
one chlorine increases acidity by a factor of 100
increasing the inductive effect
what is trichloroacetic acid?
strong acid
what are the electron donating groups?
opposite effect
increases electron density
destabilizing base
therefore forming weaker acid
what are the most common electron donating group?
alkyl groups
how does hybridization effect acidity?
the hybridization of carbon atom attached to acidic H effects acidity
the more S orbital an atom has the closer it is to the nucleus so more electronegative, and more acidic and more stable
which are more electronegative: sp, sp2, sp3?
sp most
sp2
sp3 lowest
how is delocalization of charge in base a stabilising factor?
through resonance
effect of halogen group in a benzene?
the closer it is to the carboxyl group the lower the pKa
effect of nitrophenols in benzene with ortho or para names?
further delocalization of acidic charge
increasing acidity
is m-nitrophenol less acidic for having a higher pKa than o-nitrophenol and p-nitrophenol?
no because inductive effect helps stabilize the anion
effect of more nitroxide groups on a phenol?
if there are more nitroxide groups on a phenol the more acidic it is
