Concept explainers
Interpretation:
The structure of the resulting azide is to be determined and the difference in reactivity between the two diastereomers is to be explained.
Concept introduction:
Azide is an ionic base and a good nucleophile, so the mechanisms of substitution/elimination reaction using azide will be
In
In
mechanism, the nucleophile approaches from the less hindered side.
The anti-coplanar geometry of the beta proton and the leaving group increase the
The low level of steric hindrance increase the rate of substitution reaction.
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning