Answer Happy

Question 2. The following are all weak bases; however, you should be able to determine their relative basicity. For the following pairs of bases, identify the weaker base and match the explanation with the pair. Note: The more stabilized the lone pair of electrons being donated to an acid, the less basic the compound is. NO₂ O₂N. NH₂ N 3 CH3 10 5 "NH₂ NH₂ Fill in the chart: Weaker base Answer Correct Explanation 10 Marks total 1 or 2 2 Marks 2 Marks 3 or 4 2 Marks 5 or 6 2 Marks 7 or 8 2 Marks 9 or 10 a) Resonance onto electronegative atoms is more stabilizing than less electronegative atoms b) Resonance is more stabilizing than hybridization c) Electron withdrawing groups stabilize the lone pair on the nitrogen by inductively withdrawing electron density away from the nitrogen, bringing the lone pair on the nitrogen closer to the nucleus - electrons closer to the nucleus are more stable. d) sp² nitrogens are less reactive than sp³ nitrogens because the lone pair is closer to the nucleus. e) The lone pair on the amine delocalized onto the electron-withdrawing group, increasing the stability and decreasing the lone pair's reactivity. 6 NH₂ 8 NH₂