?Benzoic acid \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\right)\) and aniline

Chapter 16, Problem 16.11

(choose chapter or problem)

Benzoic acid \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\right)\) and aniline \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\right)\) are both derivatives of benzene. Benzoic acid is an acid with \(K_{a}=6.3 \times 10^{-5}\) and aniline is a base with \(K_{a}=4.3 \times 10^{-10}\).

(a) What are the conjugate base of benzoic acid and the conjugate acid of aniline?

(b) Anilinium chloride \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3} \mathrm{Cl}\right)\) is a strong electrolyte that dissociates into anilinium ions \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}^{+}\right)\) and chloride ions. Which will be more acidic, a 0.10 M solution of benzoic acid or a 0.10 M solution of anilinium chloride?

(c) What is the value of the equilibrium constant for the following equilibrium?

\(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}(a q)+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}(a q) & \rightleftharpoons \\

\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COO}^{-}(a q)+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}^{+}(a q)\)

Text Transcription:

(C6H5COOH)

(C6H5NH2)

Ka = 6.3 x 10-5

 Ka = 4.3 x 10-10

(C6H5NH3Cl)

(C6H5NH3 +)

C6H5COOH(aq) + C6H5NH2(aq) rightleftharpoons

C6H5COO-(aq) + C6H5NH3 +(aq)