A hydrogen atom in the organic base pyridine, C 5 H 5 N, can be substituted by various atoms or groups to give XC 5 H 4 N, where X is an atom such as Cl or a group such as CH 3 The following table gives K a values for the conjugate acids of a variety of substituted pyridines (a) Suppose each conjug...

a The solution with the highest pH would be the one with the weakest conjugate acid which is the one ...

A hydrogen atom in the organic base pyridine, C 5 H 5 N, can be substituted by

Question:

A hydrogen atom in the organic base pyridine, C₅H₅N, can be substituted by various atoms or groups to give XC₅H₄N, where X is an atom such as Cl or a group such as CH₃. The following table gives K_a values for the conjugate acids of a variety of substituted pyridines. N (aq) + HCl(aq) X substituted pyridine H+ N X conjugate acid (aq) + Cl (aq)

Atom or Group X K of Conjugate Acid 5.9 x 10-2 1.5 x 10-4 6.8 x 10-6 1.0 x 10-6 NO CI H CH3

(a) Suppose each conjugate acid is dissolved in sufficient water to give a 0.050 M solution. Which solution would have the highest pH? The lowest pH?
(b) Which of the substituted pyridines is the strongest Brønsted base? Which is the weakest Brønsted base?

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