CHAPTER 9: Question 10

 

2D Explanations

If the alkene is treated as the nucleophile, then during the reaction electrons will be donated into the LUMO of the alkene, and if the diene is considered as the electrophile then during the reaction electrons will be donated from the HOMO of the diene. Thus, the interaction between the LUMO of an alkene and the HOMO of a diene must be considered. This is shown below, and it is still possible for the reaction to be suprafacial with respect to both components.
 

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