Rank the amines W through Z below in order of decreasing basicity (1 = most basic). Explain your reasoning.
Electron withdrawing groups (EWG) reduce electron density and reduce basicity. Resonance delocalizes electron density and so also decreases basicity (the electrons are less available to pick up a proton).
Electron donating groups (EDG) add electron density and increase basicity.
Alkyl groups are weakly EDG (induction), and hydrogen is neither EDG nor EWG. So cyclohexylamine (compound X) is a stronger base than ammonia (compound W).
Aniline (compound Y) has resonance, so it is less basic than compound X, which does not have resonance.
N-acyl aniline (compound Z) has more resonance forms than aniline, so it will be the least basic.
So the overall over is:
(most basic) X > W > Y > Z (least basic)
MendelSet practice problem # 753 submitted by Matt on July 27, 2011.