Ch_322a_3.09

Ch_322a_3.09 - of a highly favorable equilibrium: R-NH 2 :...

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Predicting the Outcome of Acid-Base Reactions Acid-base reactions proceed to give the weaker acid and weaker base as products . This is the reaction favored by product stability and is the tendency of reactions under equilibrium control . R-C-OH O = : + Na + - OH R-C-O: O - + Na + H-O-H pK a ~ ~ 3-5 pK a = 15.7 stronger acid weaker acid stronger base weaker base products more stable than reactants Even though the above reaction is an equilibrium, only a one-way arrow is used because the equilibrium is far to the right (>99%). The practical consequence of the above reaction is that carboxylic acids (RCO 2 H) can be dissolved as their carboxylate salts in aqueous NaOH solutions.
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Another Example: Amines in Aqueous HCl Solution Amines (RNH 2 ) dissolve in hydrochloric acid solution because
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Unformatted text preview: of a highly favorable equilibrium: R-NH 2 : + H-O-H H + Cl-R-N-H H H + Cl-+ H 2 O pK a = -1.74 pK a ~ ~ 9-10 stronger acid weaker acid stronger base weaker base products are more stable than reactants This equilibrium highly favors the products on the right, which means that water-insoluble amines may be dissolved in hydrochloric acid solution. SA WA WB SB NO SA WA SB WB YES N-H Quiz 3.09 Based on the information provided below, determine if each reaction below will proceed as written. phthalimide pK a 8.3 N H 4 + Cl-ammonium chloride N: 9.2 CH 3 COO H acetic acid 4.7 :-NH + NH 3 + KCl K + + N H 4 + Cl-N:-K + + NH CH 3 COOH + CH 3 COO-K + O O O O O O O O O O...
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322a_3.09 - of a highly favorable equilibrium: R-NH 2 :...

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