Chapter 8, Problem 56PP

Interpretation Introduction

Interpretation:

The stereochemical outcome of the E2 reaction of $\text{(2S,3S)-2-Bromo-3-phenylbutane}$ when treated with strong base to produce $\text{(E)-3-phenyl-3-butene}$ should be explained by using Newman projections.

Concept introduction:

E2 elimination reaction: E2 elimination occurs in a compound when the leaving group is antiperiplaner to the β-proton in presence of strong base.

Stereospecific reaction: reaction undergoes from a stereoisomer to a unique stereoisomeric product.

Newman projection: Newman projection of molecule is one type of representations for the alkanes, where the projection visualization from one carbon to another carbon. In this Newman projection, front carbon which represented with dot is called proximal and the back carbon which represented with circle is called distal.

From the angle of observer the front carbon is proximal and second carbon is distal.

In wedge-dash line representation wedge is coming out of the plane and dash is going behind the plane, the wedge line and the dash line of front carbon in Newman projection are pointing up and the wedge line and the dash line of back carbon in Newman projection are pointing down.