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
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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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