Chapter 18.SE, Problem 48AP

Interpretation Introduction

Interpretation:

The stereochemistry of the product formed during the acid-catalyzed hydrolysis of trans-5, 6-epoxydecane is to be given. How the product differs from that formed from cis-5, 6-epoxydecane.

Concept introduction:

The acid protonates the epoxide and then water attacks the protonated epoxide to yield the diol. When both epoxide carbons are either primary or secondary the nucleophilic attack of water mainly occurs at the less highly substituted side. When one of the epoxide carbons is tertiary, the nucleophilic attack of water mainly occurs at the more highly substituted side.

To give:

The stereochemistry of the product formed during the acid-catalyzed hydrolysis of trans-5, 6-epoxydecane is to be given. How the product differs from that formed from cis-5, 6-epoxydecane.