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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:(a) Draw the product of the following [4 + 2] cycloaddition, which was carried out in the early stages of the synthesis of the alkaloid reserpine (Problem 22.83). Indicate the stereochemistry at any newly formed stereogenic centers. (b) Draw the porbitals of the alkene and the terminal carbons of the conjugated diene, and show how the orientation of the reactants and orbital overlap lead to the observed stereochemistry.

Question: (a) What product is formed by the Claisen rearrangement of compound Z? (b) Using what you have learned about ring-closing metathesis in Chapter 26, draw the product formed when the product in part (a) is treated with Grubbs catalyst. These two reactions are key steps in the synthesis of garsubellin A, a biologically active natural product that stimulates the synthesis of the neurotransmitter acetylcholine. Compounds of this sort may prove to be useful drugs for the treatment of neurodegenerative diseases such as Alzheimer’s disease.

Question:Show that a thermal suprafacial addition is symmetry allowed in a [4 + 2] cycloaddition by using the HOMO of the alkene and the LUMO of the diene.

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

Question: Draw the product formed (including stereochemistry) in each pericyclic reaction.
See all solutions

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