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Exercise Solutions
Lewis acid: A molecule or ion that accepts a pair of electrons to form a new
covalent bond.
Lewis base: A molecule or ion that donates a pair of electrons to form a new
covalent bond.
Solution 1:
a. Butyric acid is similar in structure to CH3CO2H (acetic acid), in that both
are carboxylic acids. The pKa of acetic acid is 4.78. Therefore we can
estimate the pKa of butyric acid to be approximately 4 - 5.
b. The closest structural match for the oxonium ion in the pKa table is the
hydronium ion (H3O+), pKa -1.74. Thus we can estimate the pKa of
CH3OH2+ to be approximately -2.
The pKa table is also useful to estimate the position of a proton transfer
equilibrium. Such reactions are common in many aspects of chemistry and
biology. Any equilibrium favors the thermodynamically most stable side. In
the case of a proton transfer reaction, the equilibrium favors the side with the
weakest acid and weakest base. Because a stronger conjugate acid yields a
weaker conjugate base, base strength can be determined from the pKa table.
Analysis of the relative acid and base strengths suggests that this equilibrium
lies to the right.
Exercises:
Estimate the pKa of the circled hydrogens.