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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: What compound forms geranial (Figure 21.6) by a Cope rearrangement ?

Question: What type of cycloaddition occurs in Reaction [1]? Draw the product of a similar process in Reaction [2]. Would you predict that these reactions occur under thermal or photochemical conditions?

Question: What cyclic product is formed when each decatetraene undergoes thermal electrocyclic ring closure?

Question: Use curved arrows and draw the product of each electrocyclic reaction.

Question: Draw the product of each electrocyclic reaction.

a. the thermal electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-triene

b. the photochemical electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-triene

c. the thermal electrocyclic ring-opening of cis-5-ethyl-6-methylcyclohexa-1,3-diene

d. the photochemical electrocyclic ring-opening of trans-5-ethyl-6-methylcyclohexa-1,3- diene

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