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Evidence that cleavage of 1, 2-diols by HIO 4 occurs through a five- membered cyclic periodate intermediate is based on kinetic data —the measurement of reaction rates. When diols A and B were prepared and the rates of their reaction with HI04 were measured, it was found that diol A cleaved approximately 1 million times faster than diol B . Make molecular models of A and B and of potential cyclic periodate intermediates, and then explain the kinetic results.

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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 8.SE, Problem 68AP
Textbook Problem
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Evidence that cleavage of 1, 2-diols by HIO4 occurs through a five- membered cyclic periodate intermediate is based on kinetic data—the measurement of reaction rates. When diols A and B were prepared and the rates of their reaction with HI04 were measured, it was found that diol A cleaved approximately 1 million times faster than diol B . Make molecular models of A and B and of potential cyclic periodate intermediates, and then explain the kinetic results.

Chapter 8.SE, Problem 68AP, Evidence that cleavage of 1, 2-diols by HIO4 occurs through a five- membered cyclic periodate

Interpretation Introduction

Interpretation:

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

Organic Chemistry, Chapter 8.SE, Problem 68AP

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.

Explanation of Solution

Answer & Explanation:

In the cis diol A the two –OH groups are in the same plane. The formation of the five membered cyclic periodate will be thus easier. In trans-diol (B) the two –OH groups are in opposite planes. The formation of the five membered cyclic periodate intermediate in this case will introduce a severe steric strain in the molecule making it less stable...

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Organic Chemistry
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