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In the case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles while one on C1 is unreactive towards nucleophiles. Rationalize this difference in behavior. 0

In the case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles while one on C1 is unreactive towards nucleophiles. Rationalize this difference in behavior. 0

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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In the case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles while one on C1 is unreactive towards nucleophiles. Rationalize this difference in behavior. N 14 UNREAD MESSAGES 6 Examination of the resonance structures that can be drawn in the SNAr intermediate in the first case reveals that the five -membered ring has cyclopentadienyl character. This is a stabilizing feature. In the latter case, anion Seven Membered ring electrons in that ring, which is not a electron-delocalization in the seven -membered ring results in stabilizing feature.
Transcribed Image Text:In the case of halogen-substituted azulenes, a halogen atom on C6 can be displaced by nucleophiles while one on C1 is unreactive towards nucleophiles. Rationalize this difference in behavior. N 14 UNREAD MESSAGES 6 Examination of the resonance structures that can be drawn in the SNAr intermediate in the first case reveals that the five -membered ring has cyclopentadienyl character. This is a stabilizing feature. In the latter case, anion Seven Membered ring electrons in that ring, which is not a electron-delocalization in the seven -membered ring results in stabilizing feature.
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