Classifying types of pericyclic reaction


Assignment:

(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.

1291_Sigmatropic.JPG

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

1116_Molecular Orbit.JPG

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.

1467_pericyclic reaction.JPG


(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.

44_Sigmatropic rearrangements.JPG

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Chemistry: Classifying types of pericyclic reaction
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