Reactions of Aromatic Compounds
Reactions of Aromatic Compounds
Reactions of Aromatic Compounds
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(4) Acid-Base Equilibrium<br />
:O:<br />
S O:<br />
.<br />
. O<br />
.<br />
= =<br />
-<br />
: :<br />
Synthetic Applications<br />
+ H 3O<br />
fast<br />
+ S<br />
:O:<br />
O-H<br />
.<br />
.<br />
. O.<br />
= =<br />
: :<br />
Benzenesulfonic acid<br />
pKa = 0.699<br />
+ H 2O<br />
Although introduction <strong>of</strong> a sulfonic acid group is generally <strong>of</strong> more<br />
limited interest than other electrophilic substitution reactions, the<br />
reversibility <strong>of</strong> sulfonation leads to its use in synthetic strategy.<br />
Heating arylsulfonic acids in dilute sulfuric acid removes the sulfonic<br />
acid function.<br />
SO 3H<br />
+ H 2O<br />
heat<br />
dilute H 2SO 4<br />
+ H 2SO 4
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