Propose a mechanism for the following Cope rearrangement.

Short Answer

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Question: Describe the mechanism of the Cope rearrangement in a 1,5-diene system. Answer: The mechanism of the Cope rearrangement in a 1,5-diene system involves a [3,3]-sigmatropic shift with a concerted movement of electron pairs. This leads to the formation of a new double bond between the second and sixth atom, while breaking the original double bonds between the first and second atom, and between the fourth and fifth atom. Simultaneously, new single bonds are formed between the first and fourth atom, and between the fifth and sixth atom. The transition state during this rearrangement is stabilized by the delocalization of electron pairs over the six atoms in the 1,5-diene system. The final product has a new double bond between the second and sixth atom, and new single bonds between the first and fourth atom, and between the fifth and sixth atom.

Step by step solution

01

Identify the 1,5-diene system

First, identify the 1,5-diene system in the given molecule. The 1,5-diene system consists of a chain of six atoms, with double bonds at the first and fifth positions.
02

Formation of the new double bond

In the Cope rearrangement, the [3,3]-sigmatropic shift involves movement of electron pairs in a concerted way to form a new double bond. The new double bond will be formed between the second and sixth atom of the 1,5-diene system.
03

Breaking of the old double bonds

As the new double bond is formed, the old double bonds (between the first and second atom, and between the fourth and fifth atom) will break. The electron pairs from these double bonds will shift to form new single bonds between the first and fourth atom, and between the fifth and sixth atom.
04

Stabilization of the transition state

During the Cope rearrangement, the transition state is stabilized by the delocalization of electron pairs over the six atoms in the 1,5-diene system. This delocalization allows for the simultaneous breaking and forming of the bonds without the need for any intermediates.
05

Final product

After the completion of the Cope rearrangement, the final product formed has a new double bond between the second and sixth atom, and new single bonds between the first and fourth atom, and between the fifth and sixth atom. This constitutes the overall reaction mechanism of the Cope rearrangement.

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