Cyclic Compounds

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The syn arrangement is eclipsed. Optional: if you want to know why periplanarity is important, look at the discussion of a forced syn elimination. Maybe at this point it suffices if you realize that in the product, the alkene, the pi bond consists of two p orbitals in the same plane.

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This preference controls the stereochemical outcome of the E2 reaction. If we place the Br and the H in one particular isomer of 1-bromo-1,2-diphenylpropane see below in an anti position, all other substituents are fixed and preset for their positions in the alkene.


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Next try to determine whether the Z or the E alkene is formed by dehydrohalogenation of the following structures. In structure 1 H and Br are already in an anti position; in 2 you have to imagine what happens if you rotate around the central bond. Indicate for both structures whether they lead to the Z - or the E -1,2-diphenylpropene.

Now that we have a basic knowledge of the E2 elimination reaction in acyclic compounds, we will have a look at the same reaction on cyclic compounds. In this particular case, we will look at substituted cyclohexanes.

In cyclic structures, free rotation around the single bonds, as in compound 2 above, is not possible. What is left of this degree of freedom is the ring flip, which interchanges the axial and equatorial positions. At this point it is important to note that an anti arrangement of the two groups to be eliminated, requires both of them to occupy axial positions.

cyclic compound

In structure 1 H and Br are already in an anti position; in 2 you have to imagine what happens if you rotate around the central bond. Indicate for both structures whether they lead to the Z - or the E -1,2-diphenylpropene. Now that we have a basic knowledge of the E2 elimination reaction in acyclic compounds, we will have a look at the same reaction on cyclic compounds.

In this particular case, we will look at substituted cyclohexanes.

IUPAC Nomenclature of Cyclic Compounds

In cyclic structures, free rotation around the single bonds, as in compound 2 above, is not possible. What is left of this degree of freedom is the ring flip, which interchanges the axial and equatorial positions.

Introduction

At this point it is important to note that an anti arrangement of the two groups to be eliminated, requires both of them to occupy axial positions. It also implies that they have a trans relation.


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For a halogen to be eliminated, it should have a hydrogen in a trans position. Keeping this in mind, look at the models below.

Aromatics and Cyclic Compounds | Crash Course Chemistry | PBS LearningMedia

Question: How many products will be formed? Neomenthyl chloride differs from the previous compound in the position of the chlorine. Here it is cis to the isopropyl group.

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