Chapter 18.SE, Problem 50AP

Interpretation Introduction

Interpretation:

Imagining that the epoxide ring in (2R, 3R)-2, 3-epoxy-3-methylpentane is opened when treated with aqueous acids. a) The structure of the epoxide with stereochemistry is to be drawn. b) The name and structure of the product with stereochemistry are to be given. c) Whether the product is chiral or not is to be explained. d) Whether the product is optically active or not is to be explained.

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 draw:

The structure of the epoxide with stereochemistry.

To give:

The name and structure of the product with stereochemistry.

To explain:

Whether the product is chiral or not and whether the product is optically active or not.