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Chapter 27: Q 59. (page 1104)

Question: What product is formed by [3,3] sigmatropic rearrangement of the following compound? Clearly indicate the stereochemistry around all tetrahedral stereogenic centers.

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01

[3,3] sigmatropic rearrangement

The net change in the number of σ-bonds is zero. This rearrangement requires little to no heat; no catalyst is required. Along with the change of the position of a -bond, the position of a group is changed.

02

Ring stability

The driving force for this rearrangement to occur is the instability of the five-membered small ring with a double bond and a hydroxide group in close proximity of the C=C.

03

Mechanism of the given reaction

The -bond from the -bond is rearranged to change the position of the group. The rearrangement takes place in between the two -bonds and a -bond. The mechanism of the rearrangement is given hereunder

The product of rearrangement has the OH group far from the C=C of the five-membered ring.

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Most popular questions from this chapter

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.

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.

Question: Draw the product of the [3,3] sigmatropic rearrangement of each compound.

Question: Using the Woodward–Hoffmann 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

Question: Draw the product formed when diene M undergoes disrotatory cyclization. Indicate the stereochemistry at new hybridized carbons. Will the reaction occur under thermal or photochemical conditions?
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