Acetanilide resonance structures

Asked by maham237 @ 12/01/2021 in Chemistry viewed by 279 People

Draw the most stable resonance structure for the intermediate in the electrophilic aromatic bromination of aniline, anisole, and acetanilide to make the respective monobrominated products. compare their relative stability and the predict the relative reactivities of each starting compound.

Answered by maham237 @ 12/01/2021

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

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Acetanilide resonance structures

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