Chapter 24, Problem 24.22P

Interpretation Introduction

Interpretation:

Compound A will undergo periodate oxidative cleavage but B will not. The reason for it is to be explained. The product of the reaction between A and ${\text{HIO}}_{\text{4}}$ is to be drawn including stereochemistry.

Concept introduction:

An alkene can be cleaved oxidatively by treatment with ${\text{OSO}}_{\text{4}}$, followed by the

periodate anion, ${\text{IO}}_{\text{4}}{}^{\text{-}}$. The addition of ${\text{IO}}_{\text{4}}{}^{\text{-}}$ produces a cyclic periodate ester. The final step in the mechanism is the key, because it cleaves the C-C bond and produces the two carbonyl groups. This step is a [4+2] cyclo elimination. Periodate oxidative cleavage can be carried out directly on a 1, 2-diol.