The correct increasing order of basic strength for the following compounds is [figure]
- III < I < II
- III < II < I
- II < I < III
- II < III < I
Answer
(3) II < I < III
Solution
In arylamines the lone pair of N is delocalised into the ring; the more available the lone pair, the stronger the base.
II: -NO2 at para position withdraws electrons (-R, -I) ⇒ lone pair on N is least available ⇒ weakest base.
III: -CH3 at para position releases electrons (+I, hyperconjugation) ⇒ lone pair more available than in aniline ⇒ strongest base.
As per NCERT, pKb values: p-nitroaniline = 13.0, aniline = 9.38, p-toluidine = 8.92 (lower pKb ⇒ stronger base).
∴ Increasing order of basic strength: II < I < III.
Answer: (3)