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Sigmatropic rearrangements

(a) The pericyclic reaction shown below is an example of the Cope rearrangement.

(i) Classify the sigmatropic rearrangement as an [n,n]-sigmatropic rearrangement, where n is an integer. Show how the classification is arrived at as part of your answer.

Please see the attached document for the diagram.

(ii) An incomplete Molecular Orbital diagram for the Frontier Orbital approach to the above sigmatropic rearrangement is shown below.

Please see the attached document for the diagram.

Complete the Molecular Orbital diagram. As part of your answer, define all of the terms used and explain the meaning of any symbols. There is no need to apply the frontier orbital approach for this pericyclic reaction.

(b) Identify and classify the type of pericyclic reaction shown below and use Frontier Orbital Analysis to identify the reaction conditions under which the reaction will proceed. As part of your answer, draw the appropriate Molecular Orbital diagrams and define all new terms and symbols used as part of your answer.

Please see the attached document for the diagrams.

(c) The photochemical electrocyclic 4 electron reaction of the E,Z-hexa-2,4-diene is shown below. Use Frontier Orbital Analysis to identify the stereochemistry of the 1,2-dimethylcyclobutene product. As part of your answer define any new terms that you use.

Please see the attached document for the diagrams.

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Solution Summary

A Cope rearrangement example is classified as an [n,n] rearrangement. An MO diagram is also given for the reaction. Additionally, FMO analysis is carried out.

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