Chapter 10, Problem 10.51P

Interpretation Introduction

Interpretation:

It is to be explained why the attempt to synthesize an epoxide according to the given reaction scheme failed.

Concept introduction:

Epoxides are three membered ring ethers and can be made using halohydrins. Halohydrins are the compounds containing a halogen and a hydroxyl group on adjacent carbon atoms. When a halohydrin is treated with a strong base, the strong base deprotonates the hydrogen atom in the hydroxyl group in halohydrin. The negatively charged oxygen atom then attacks the carbon atom to which the bromine or halogen atom is attached to form an epoxide via an ${\text{S}}_{\text{N}}\text{2}$ reaction pathway.

In the most stable form of substituted cyclohexane, the bulkiest group occupies the equatorial position. The substituents attached to the cyclohexane are cis if they lie on the same side of the plane of the ring, and they are trans if they lie on the opposite side of the plane of the ring.