Artboard Created with Sketch. Close Search Dialog
! Error Created with Sketch.

Organic Chemistry: Sn2E2 Reactions

Chemistry
Summary

Problems 2

Summary Problems 2

Problem :

Will compound X undergo an E2 reaction? State your reasoning.

Compound X will not undergo an E2 reaction. It has no β-hydrogens.

Problem :

Predict the product of the following E2 reaction. Assume that there is no rotation about the C-C bond.

Problem : Predict the major product of the following E2 reaction:

According to Saytzeff's rule, the major product will be the most substituted alkene.

Problem :

The large tert-butyl group locks the ring into its current conformation.

Using the molecular orbital theory, determine whether this molecule is a good candidate for the E2 reaction and explain why.

This conforomation of the molecule is not a good candidate for the E2 reaction. All three β-hydrogens are locked into a non-antiperiplanar conformation. Thus there will be no electron density to donate into the σ* C-Br antibond.

Let's see how the situation would change if the carbon-bromine bond had been in an axial instead of an equatorial conformation. In this case there would be antiperiplanar β-hydrogens, and E2 would be possible.