Forming ionic compounds:
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Answer:
Here's what I get
Explanation:
(a) Intermediates
The three structures below represent one contributor to the resonance-stabilized intermediate, in which the lone pair electrons on the heteroatom are participating (the + charge on the heteroatoms do not show up very well).
(b) Relative Stabilities
The relative stabilities decrease in the order shown.
N is more basic than O, so NH₂ is the best electron donating group (EDG) and will best stabilize the positive charge in the ring. However, the lone pair electrons on the N in acetanilide are also involved in resonance with the carbonyl group, so they are not as available for stabilization of the ring.
(c) Relative reactivities
The relative reactivities would be
C₆H₅-NH₂ > C₆H₅-OCH₃ > C₆H₅-NHCOCH₃
