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Chapter 27: Q 55. (page 1103)

Question: Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.

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01

Electrocyclic reaction

The reactions that involve the conversion of a pi bond of a conjugated system to a sigma bond or vice-versa are named electrocyclic reactions.

Conjugated systems involving an even number of pi electrons undergo conrotation, while conjugated systems with an odd number of pi electrons undergo disrotation under thermal conditions.

02

Preparation of the given product

The conversion of the starting material to the given product involves two main steps:

  • 8 pi electrocyclic ring-opening (conrotatory) and
  • 6 pi electrocyclic ring-opening (conrotatory).

The reactions are shown below.

Reactions involved in the formation of the product

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Most popular questions from this chapter

Question:Show that a thermal suprafacial addition is symmetry allowed in a [4 + 2] cycloaddition by using the HOMO of the alkene and the LUMO of the diene.

Question: What type of cycloaddition occurs in Reaction [1]? Draw the product of a similar process in Reaction [2]. Would you predict that these reactions occur under thermal or photochemical conditions?

Question: Use curved arrows and draw the product of each electrocyclic reaction.

Question: Draw a stepwise, detailed mechanism for the following reaction.

Question: What product is formed when each compound undergoes a photochemical electrocyclic reaction? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.
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