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Hypohalous Acids

The most common hypohalous acids, HOCl and HOBr, are relatively weak acids (pKa = 7.5 & 8.6 respectively) that are only stable in solution. These acids and their ester derivatives are formed reversibly when the corresponding halogens are dissolved in hydroxylic solvents.

X2 + H2O equilibrium arrow HOX + HX
X2 + ROH equilibrium arrow ROX + HX

For a solution of chlorine in water the equilibrium constant is only about 5 * 10-4. The concentration of HOCl may be increased by adding silver oxide ( Ag(+) reduces the chloride ion concentration and the oxide increases the pH ), but this is not a common procedure. As a rule, these reagents are prepared by hydrolysis of N-chloro and N-bromo precursors immediately prior to their use.

Hydrolysis of N-bromoacetamide to HOBr plus acetamide, and trichloroisocyanuric acid to 3 HOCl plus isocyanuric acid

Virtual Textbook: Alkenes — Hypohalous Acids, figure 1Virtual Textbook: Alkenes — Hypohalous Acids, figure 2