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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: 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

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

Question:Consider cycloheptatrienone and ethylene, and draw a possible product formed from each type of cycloaddition:

(a) [2 + 2]

(b) [4 + 2]

(c) [6 + 2]

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: Classify each reaction as an electrocyclic reaction, a cycloaddition, or a sigmatropic rearrangement. Label the 蟽 bonds that are broken or formed in each reaction.
See all solutions

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