Question #cbdcf
1 Answer
Some esters are good leaving groups.
Explanation:
If a good nucleophile is a strong base, a good leaving group is a weak base.
Another way of saying it is, A good leaving group is the conjugate base of a strong acid.
Consider the reaction
The ester of a carboxylic acid is not a good leaving group because the carboxylate ion
Some common strong acids are
-
trifluoromethanesulfonic acid (
#"CF"_3"SO"_3"H", "TfOH"# ),#color(white)(l)"p"K_a "= -14"# -
p-toluenesulfonic acid (
#"CH"_3"C"_6"H"_4"SO"_3"H", "TsOH"# ),#color(white)(ll)"p"K_a "= -2.8"# -
methanesulfonic acid (
#"CH"_3"SO"_3"H", "MsOH"# ),#color(white)(mmml)"p"K_a "= -2.6"#
Their esters make good leaving groups.
They also have the advantage that their esters are usually solids and therefore easier to handle.
If you want to convert an