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.

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7.57
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.
Transcribed Image Text:7.57 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.
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