Chemistry Reference
In-Depth Information
Scheme 3.1 General representation of bases reacting with acids.
Common base classes and examples of bases used in organic chemistry are shown in
Figure 3.1 along with their conjugate acids and associated pK
a
values.
In looking at the conjugate acid pK
a
values listed in Figure 3.1, we realize that in order
for the reactions represented in Scheme 3.1 to occur, the conjugate acid of a given base must
have a pK
a
value that is higher than the pK
a
value associated with a proton of interest. For
example, as shown in Scheme 3.2, we would not expect triethylamine to effectively depro-
tonate methyl acetate because the pK
a
of methyl acetate is 15 pK
a
units higher than the pK
a
Figure 3.1 Common bases used in organic chemistry.
