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Chapter 27: Q 57. (page 1104)

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.

Short Answer

Expert verified

Answer

Step 1- Ring-opening

Step 2- Ring-closing

Step by step solution

01

Ring-opening reaction

The smaller ring is less stable than the large rings. On heating, the small ring undergoes a ring-opening reaction by following the conrotation of the molecular orbitals.

02

Ring-closing reaction

On heating, the 6 蟺-molecular orbitals undergo a ring-closing reaction by following disrotation of the molecular orbitals.

03

Explanation of the given reaction

The first step is the ring-opening reaction as the smaller rings are strained; hence they undergo a ring-opening reaction quickly even on less heating.

In the next step, the two reactants undergo a ring-closing reaction by following the disrotation of molecular orbitals.

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Most popular questions from this chapter

Question: What product is formed from the Cope or oxy-Cope rearrangement of each starting material?

Question:What product would be formed by the disrotatory cyclization of the given triene? Would this reaction occur under photochemical or thermal conditions?

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: Draw the product of each Diels鈥揂lder reaction and indicate the stereochemistry at all stereogenic centers

Question: Using the Woodward鈥揌offmann rules in Table 27.4, predict the stereochemistry of each reaction.

a. a [6 + 4] thermal cycloaddition

b. photochemical electrocyclic ring closure of deca-1,3,5,7,9-pentaene

c. a [4 + 4] photochemical cycloaddition

d. a thermal [5,5] sigmatropic rearrangement
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