L3 Acids and Bases Flashcards
(18 cards)
Which side does acid/base rxn favor?
weaker reagents
Factors influencing acidity/bascicity
FC, EN of reactive site, induction effect, resonance
Positive formal charge effect on acidity
increased acidity
Positive formal charge effect on bascisity
decreased bascisity
Negative formal charge effect on bascisity
increased bascisity
Negative formal charge effect on acidity
decreased acidity
Explanation of formal charge effect on acidity/bascisity
columb’s law - positive charge repels proton, negative charge attracts proton
High EN of atom @ reactive site effect on acidity
increased acidity - the dipole creates a larger partial + on H
High EN of atom @ reactive site effect on bascisity
decreased bascisity - the partial - is stabilized by the more EN nucleus
Low EN of atom @ reactive site effect on bascisity
increased bascisity
Low EN of atom @ reactive site effect on acidity
decreased acidity
Inductive effect definition
nearby EN atoms skew e density towards themselves and away from reactive site
Inductive effect relationship on acidity
increased acidity - less e density»_space; more positive»_space; repels proton more
Inductive effect relationship on bascicity
decreased bascisity - EN atoms pull e density away from hydrogen acceptors
In general, what makes an acid stronger?
Anything that increases the partial + on H
In general, what makes a base stronger?
Anything that increases the willingness of an atom to accept H+
the more resonance structures that have - charge on carbon…the more acidic/basic
more acidic; the - charge is stabilized by being smeared across more carbons
if no resonance available…
turn it to its con. base (remove H+) then do resonance and use acid/base relationships
