The reactant shown, having an axial p-toluenesulfonate in its most stable conformation, undergoes predominant elimination on reaction with sodium azide. TsO NaN3 N3 (46%) (37%) Its diastereomer having an equatorial p-toluenesulfonate gives predominant substitution (76%). Give the structure of the resulting azide and suggest an explanation for the difference in reactivity between the two diastereomeric p-toluenesulfonates.

The reactant shown, having an axial p-toluenesulfonate in its most stable conformation, undergoes predominant elimination on reaction with sodium azide. TsO NaN3 N3 (46%) (37%) Its diastereomer having an equatorial p-toluenesulfonate gives predominant substitution (76%). Give the structure of the resulting azide and suggest an explanation for the difference in reactivity between the two diastereomeric p-toluenesulfonates.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.55P

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