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Chapter 25: PROBLEM 24.17 (page 1016)

Question: Draw the products of each acid鈥揵ase reaction. Indicate whether equilibrium favors the reactants or products.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Equilibrium  

The pKa of many protonated amines is 10鈥�11. So, the pKa of the starting acid must be less than 10 for the equilibrium to favor the products.

Amines are thus readily protonated by strong inorganic acids, such as HCl and H2SO4 and by carboxylic acid (organic acid) as well.

02

Explanation

a. The reaction of the butane amine is represented as

pKavalues of HCl is -7

The pKa of the product is 10. Therefore, the product is a weaker acid.

b. The reaction of the piperidine with water does not favor the product, as shown below.

Favored equilibrium

c. The reaction of the given amine is represented a

pKa value of CH3COOH is 4.2

pKa (CH3)2NH2+ is 10.7

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