Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable?
A)I
B)II
C)III
D)IV
E)None of these choices.

Question

Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable? 
A)I 
B)II 
C)III 
D)IV 
E)None of these choices.

Quizplus · Accepted Answer

Contributor II involves the delocalization of the lone pair of electrons on the nitrogen atom into the ring, creating a stable aromatic system. This is known as the "aniline resonance structure" and is commonly seen in substituted anilines. Therefore, Contributor II is exceptionally stable.

Which of the Following Contributors to the Resonance Stabilized Hybrid