CARBOXYLIC ACIDS50319.2Ionization of peroxy acids such as peroxyacetic acid yields an anion that cannot be stabilized by res-onance in the same way that acetate can.19.3Recall from Chapter 4 (text Section 4.6) that an acid–base equilibrium favors formation of theweaker acid and base. Also remember that the weaker acid forms the stronger conjugate base, andvice versa.(b)The acid–base reaction between acetic acid andtert-butoxide ion is represented by the equationAlcohols are weaker acids than carboxylic acids; the equilibrium lies to the right.(c)Bromide ion is the conjugate base of hydrogen bromide, a strong acid.In this case, the position of equilibrium favors the starting materials, because acetic acid is aweaker acid than hydrogen bromide.(d)Acetylide ion is a rather strong base, and acetylene, with a Kaof 1026, is a much weaker acidthan acetic acid. The position of equilibrium favors the formation of products.(e)Nitrate ion is a very weak base; it is the conjugate base of the strong acid nitric acid. Theposition of equilibrium lies to the left.
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