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Chapter 27: Q 14. (page 1090)

Question:Draw the product (including stereochemistry) formed from each pair ofreactants in a thermal [4 + 2] cycloaddition reaction.

Short Answer

Expert verified

For a [4+2] cycloaddition, the bond formation can occur superficially under thermal conditions.

The [4+2] cycloaddition considering HOMO of diene and LUMO of alkene is shown below:

Bond formation between HOMO of diene and LUMO of alkene

Step by step solution

01

[4+2] Cycloaddition reactions

For a [4+2] cycloaddition, the bond formation can occur superficially under thermal conditions.

The [4+2] cycloaddition considering HOMO of diene and LUMO of alkene is shown below:

Bond formation between HOMO of diene and LUMO of alkene

02

Determination of products

a. Both the reactants are redrawn, and the [4+2] cycloaddition is carried out. The product is shown below:

b. Both the reactants are redrawn, and the [4+2] cycloaddition is carried out. The product is shown below:

[4+2] cycloaddition of compound b

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Most popular questions from this chapter

Question: Use curved arrows to show how E is converted to F by a two-step reaction sequence consisting of a [1,5] sigmatropic rearrangement followed by a [4 + 2] cycloaddition.

Question:Using the Woodward鈥揌offmann rules, predict the stereochemical pathway for each cycloaddition:

(a) a [6 + 4] photochemical reaction;

(b) an [8 + 2] thermal reaction.

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 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: A solution of 5-methylcyclopenta-1,3-diene rearranges at room temperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products are formed from the starting material by a sigmatropic rearrangement involving a C鈥揌 bond. (b) Explain why 2-methylcyclopenta-1,3-diene is not formed directly from 5-methylcyclopenta-1,3-diene by a [1,3] rearrangement.
See all solutions

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