Chapter 8.SE, Problem 68AP

Interpretation Introduction

Interpretation:

The observation that cis-diol A cleaved approximately I million times faster than the trans-diol B is to be explained.

Concept introduction:

The cleavage of diols by HIO₄ takes place through the formation of a five membered cyclic periodate intermediate. In the diol if the two –OH groups are cis- to each other then the formation of the cyclic intermediate will be easier than the diol wherein the two –OH groups are trans to each other. Thus the intermediate in the case of cis-diol will be easily formed and the reaction occurs at faster rate.

To explain:

The observation that cis-diol A cleaved approximately 1 million times faster than the trans-diol B is to be explained.