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Chapter 27: Q 47. (page 1102)

Question: What product is formed from the [5,5] sigmatropic rearrangement of the following unsaturated ether?

Short Answer

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Answer

Step by step solution

01

Step 1: [5,5]  sigmatropic shift

The 5,5sigmatropic shift is associated with the intramolecular rearrangement of the group at the fifth position and the fifth position of the other group.

The new sigma bond is formed between the fifth positions of the groups.

02

Explanation

In the given conversion, the group at the fifth position rearranges itself. Therefore, it is a 5,5 sigmatropic shift.

5,5sigmatropic shift.

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Most popular questions from this chapter

Question: The bicyclic alkene P can be prepared by thermal electrocyclic ring closure from cyclodecadiene Q or by photochemical electrocyclic ring closure from cyclodecadiene R.Draw the structures of Q and R, and indicate the stereochemistry of the process by which each reaction occurs.

Question: Consider the following electrocyclic ring closure. Does the product form by a conrotatory or disrotatory process? Would this reaction occur under photochemical or thermal conditions?

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

Question: What product is formed when each compound undergoes thermal electrocyclic ring-opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.

Question: What product is formed by the [3,3] sigmatropic rearrangement of each compound?
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