Chapter 14.SE, Problem 56AP

Interpretation Introduction

Interpretation:

Given that norbornadiene can be prepared by reaction of chloroethylene with 1,3-cyclopentadiene, followed by treatment of the product with sodium ethoxide. The overall scheme is to be written and the two kinds of the reactions involved are to be identified.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. These reactions occur rapidly with dienophiles having electron withdrawing substituent groups in conjugation with the double bond and if the diene adapts a s-cis conformation during the reaction. The reaction takes place in endo manner.

On treatment with bases, organic halides dehydrohalogenate to yield alkenes.

To write:

The overall scheme for preparing norbornadiene by reacting chloroethylene with 1,3-cyclopentadiene, followed by treating the product with sodium ethoxide and to identify the two kinds of the reactions involved.