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Organic acids and bases homework
1.
Each of the following molecules has two potential Bronsted acid protons (indicated by boxes). Draw the
conjugate base that would be formed when the MORE acidic of the two protons is deprotonated. Explain
your choice.
conjugate base:
H
N
H
conjugate base:
H
explain:
S
H
S
conjugate base:
H
explain:
O
explain:
O
F
H
O
conjugate base:
explain:
H
H
conjugate base:
H
S
O H
explain:
2.
a) Using the table of pKa values in your notes, choose a conjugate base that reacts with the acid below to
favor the products (right) at equilibrium. Draw that base as a reactant, show the curved arrow mechanism
for the reaction, and draw the correct conjugate acid and conjugate base.
F
O
H
F F
pKa = 13
b) Using the table of pKa values in your notes, choose a conjugate base that react with the acid below to
favor the reactants (right) at equilibrium. Draw that base as a reactant, show the curved arrow
mechanism for the reaction, and draw the correct conjugate acid and conjugate base.
F
O
H
F F
pKa = 13
3. a) Draw the mechanism (curved arrows) and products for the following acid/base reaction
b) Assign approximate pKa values and give the direction of the equilibrium for each reaction
O
O
O
N
H
H
O
H
O
N
O
Na
H
O
H