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 S N 2/E2 when the substrate is a secondary alcohol (or toluene sulfonate ester). In E2 elimination, the proton and the other group being eliminated must be axial and anti to each other. In S N 2 mechanism, the nucleophile approaches from the less hindered side. The anti-coplanar geometry of the beta proton and the leaving group increase the rate of elimination reaction. The low level of steric hindrance increase the rate of substitution reaction.

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Chapter 7, Problem 57P

Interpretation Introduction

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 SN2/E2 when the substrate is a secondary alcohol (or toluene sulfonate ester).

In E2 elimination, the proton and the other group being eliminated must be axial and anti to each other.

In SN2

mechanism, the nucleophile approaches from the less hindered side.

The anti-coplanar geometry of the beta proton and the leaving group increase the rate of elimination reaction.

The low level of steric hindrance increase the rate of substitution reaction.

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