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Dolbier HW Solutions 409 - 503 CARBOXYLIC ACIDS 19.2...

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CARBOXYLIC ACIDS 503 19.2 Ionization of peroxy acids such as peroxyacetic acid yields an anion that cannot be stabilized by res- onance in the same way that acetate can. 19.3 Recall from Chapter 4 (text Section 4.6) that an acid–base equilibrium favors formation of the weaker acid and base. Also remember that the weaker acid forms the stronger conjugate base, and vice versa. ( b ) The acid–base reaction between acetic acid and tert -butoxide ion is represented by the equation Alcohols 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 a weaker acid than hydrogen bromide. ( d ) Acetylide ion is a rather strong base, and acetylene, with a K a of 10 26 , is a much weaker acid than 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. The position of equilibrium lies to the left.
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