Arrange the following bases in order of increasing strength on the basis of the pK_a values of their conjugate acids, which are given in parentheses:

(a) Aniline (4.63; see Exercise 6C.12);

(b) 2-hydroxyaniline (4.72);

(c) 3-hydroxyaniline (4.17);

(d) 4-hydroxyaniline (5.47). Is there a simple pattern of strengths?

Exercise 6C.12

The value of pK_b for aniline is 9.37 and that for 4-chloroaniline is 9.85. Which is the stronger base? Account for the difference in strength.

Transcribed Image Text:

NH OH NH 2-Hydroxyaniline 3-Hydroxyaniline OH NH OH 4-Hydroxyaniline